I'm not entirely sure if another more specific sub forum would better serve this question, so hopefully just posting here is okay.

So one thing I've never had the opportunity to do is dress up fully. It's always been the stray article of clothing that doesn't fit creating mismatched outfits, and it is wholly unsatisfying. The rest of my household will be gone for a week for Thanksgiving and possibly before that, so I want to take this chance to change this and experience the whole nine yards. Shopping in a store is 100% not an option for me at the moment, so I'm left with online avenues. But after a few hours of browsing... well, I'm hopelessly lost and daunted by the expense.

First, the issue of expense... My main concern is doing things on the cheap as I am still actively losing weight so don't want to go spending hundreds on stuff that won't even fit me a month later and I may not really be able to wear again. I know a few things I can get cheap off Amazon, such as wigs, some basic makeup, etc. Then some of the best deals actually seem to be on adult stores for the undergarment types. (I'm not going for comfort here as I'm not wearing this anywhere but in my own room pretty much just to stare at myself, so am not worried too much about cheap semi-disposable materials that such places tend to traffic in.) Where I'm really running into a problem is finding suitable "discount" dresses or shoes (which I know exist because my sister constantly brags about how her outfit only cost $20 ). Some stores specializing in crossdressing have things I'm interested in, but ranging a bit higher in price than I'd like(typically around $80, but I have the feeling the quality is a bit higher than I need for this experiment so thinking it's not worth it). Does anyone have any advice on where I should be looking, and what would be a realistic price? (Ie: Maybe I shouldn't be expecting to spend less than a couple hundred at all.)

Second, does anyone know any good sites that offer crash courses in women's clothing? It seems like there has to be something out there for those of us who couldn't learn the organic way to get started with. Maybe also dealing with issues that may be common to the transgender community in particular, such as proper fitting to broader shoulders/rib cage, and so forth. (I could tell with one look that most of the cheaper options I saw on some sites were not going to fit my upper torso right even if the measurements matched.)

If you want cheap stuff, go to a second hand store. You can even take some of your clothes to trade them,

Heya [emoji5].  Cheap clothing online would be your usual suspects Amazon,  but also eBay (many people sell bundles of used clothes,  and these may even be from a coordinated wardrobe). I've had cheap Chinese import clothes from Amazon, they aren't the best quality,  but a good starter.

Google will find you articles on 'dressing for your body type', I'm still learning myself,  but I know that v-necks help to draw the eye away from larger shoulders [emoji5]. The bad news is that figuring out the colors,  cuts and styles that suit you just takes time,  but we all have to start somewhere.

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One thing that always bothered me about how I grew up was that my mom shopped for me in the most expensive stores, and bought me a ton of things that I just plain didn't like, or didn't work with my tiny frame.  So she spent a lot of money on clothes just for me to not end up wearing them.  As I've gotten older, I've learned a lot about where to shop and what I like and what looks good on me. 


Being overweight has also often been a plague for me, so I don't shop or I shop at consignment stores. I found out there's a really good one a couple miles from me and for exploring my own gender identity, its been my best friend. I think when I splurged and bought clothes for my birthday, I spent 60 or so dollars on myself?  Maybe 80? Don't remember.  Course for me I was shopping in the mens section, though I did buy two pairs of pants in the female section because none of the mens pants they had fit me.  Similar prices across both genders.  Also... WALMART! Sounds crazy and cheap, but they really do have some cute stuff for fairly good prices.  (Still not as cheap as consignment stores in a lot of cases, but pretty good)

SOOOO as for dressing yourself and what looks good on you? Start with picking out things that you like.  Just grab anything and everything off the shelf, (this is what I hate about online shopping is it is much harder to do that) and try them on.  One thing I find is that fear overwhelms us when asking what we look good in, and really, often when it comes down to it, what we like is what we look best in.  Probably because what we like is what gives us the confidence we need to rock it.

The other idea is, if you're comfortable (or in a store where its a relatively safe place) telling a store clerk you are exploring your gender identity (or hell, you just are wanting to explore crossdressing) they can help you.  If not, just say, 'I have a sister/twin/gf that I'm shopping for, and she's built a lot like me.  Can you help me pick out clothes that would look good on my body type so I can pick out something for her?'  Believe it or not, cismen have to ask for clothes for their siblings/girlfriends a lot, they are more used to it than you think.



(Copying this paragraph so you can skip above section entirely)
SOOOO as for dressing yourself and what looks good on you? Start with picking out things that you like.  Just grab anything and everything off the shelf, (this is what I hate about online shopping is it is much harder to do that) and try them on.  One thing I find is that fear overwhelms us when asking what we look good in, and really, often when it comes down to it, what we like is what we look best in.  Probably because what we like is what gives us the confidence we need to rock it.

One of the great thing about female clothing too, just a tip, is YOU DON'T HAVE TO FRET ABOUT FINDING THE RIGHT PANT LENGTH!  They aren't going to go into great detail about leg length, like you would in the mens department. A few brands might, but its actually quite rare.  Pants for women come in long, regular, and short/ankle/petite.  (Though not always, so if you are tall you may need to make sure you look for brands that have the long leg sizes.  Although in my experience when there is no specific length attached, they really do make pants extra long.  'Regular' pants cover my feet. I can wear pants like they have built in shoes hahaha)

Another tip, don't be afraid to layer. Ladies' garment tops are freakishly short half the time, so I end up wearing tank tops with almost everything. (Yeah, I have a freakishly long torso, especially given my 5'2" frame) I make sure to bring this up because as you're exploring still, its not something you might think about.


AIIIIIIIIIII I just read that you can't do instore shopping, so focus on my clothing tips...  Leaving the other stuff in in case someone else finds this thread and needs the information though.  I do think there are some consignment stores that you can shop online.  If you're not afraid of the Asian Markets, Aliexpress I think it is, is pretty cheaply priced.  There are a few others too, but that's the only one I can think of off the top of my head. Also, Walmart.com still is a good option, and they, like Amazon, also gather items from other sites and will ship to you under their store/site policies.

I don't follow many MTF people on youtube, (Think Stef Sanjati is the only one I follow?  I don't remember... Though she does do some makeup tutorials. Don't know if she talks about fashion though) so I can't help you much there.  But I do know there are toooooons of makeup videos all over youtube.  This sounds weird, but I think even FTM videos where they invite someone to do their makeup for them may even help.  There's a few gay youtubers that also do this, and they talk a lot about contouring to shape your face and stuff, but obviously looking up MTF youtubers would help most.

Also anyone here ever wear the show 'What not to wear' back in the day? Hahaha loved that show!



Edit: Bolding sections and titling so you can see where to focus because I'm dumb and didn't realize till halfway through I missed a critical piece in your post

I wish I could just go try stuff on, that would be amazing. Unfortunately, courage and acceptance aside, I am in probably one of the worst places you can be logistically for this sort of thing without being in a country town with a 3 digit population. Clothes shopping in general is a chore, as there are literally no stores that aren't overpriced boutique type places here, designed to rip off the super rich and tourists. (I'm on a resort-y/summer home centric barrier island off of Georgia, so actual stores and support for residents are slim. Takes a trek across a bridge just to even get within 15 minutes of anything, and I'm on the opposite end of the island of the bridge.)

The pants length tip is a huge one though, I haven't seen that mentioned anywhere before! I struggled to find the right pants length with men's sizes for years (what genius decided being overweight means you suddenly have longer legs too?).

Hey Roll, sucks that you're not in a good place to try stuff out...I haven't had that particular problem, but I have had the problem of finding things that fit me and are affordable. In the UK we have this mega cheap clothes shop called Primark, and they have some loose, flowy tops that will fit anyone, which are basically what I wear all the time.  I don't know if they deliver to Georgia? (Worth mentioning that they're ethically dreadful, but hey, we're desperate.) Depending on your size, you could try getting some girl jeans? Walk into a shop, pick up some guy clothes and a pair of girl jeans and try them on. I know lots of guys that wear girl jeans, since they fit better.

Quote from: Roll on September 06, 2017, 04:51:20 PM
I wish I could just go try stuff on, that would be amazing. Unfortunately, courage and acceptance aside, I am in probably one of the worst places you can be logistically for this sort of thing without being in a country town with a 3 digit population. Clothes shopping in general is a chore, as there are literally no stores that aren't overpriced boutique type places here, designed to rip off the super rich and tourists. (I'm on a resort-y/summer home centric barrier island off of Georgia, so actual stores and support for residents are slim. Takes a trek across a bridge just to even get within 15 minutes of anything, and I'm on the opposite end of the island of the bridge.)

The pants length tip is a huge one though, I haven't seen that mentioned anywhere before! I struggled to find the right pants length with men's sizes for years (what genius decided being overweight means you suddenly have longer legs too?).

Dude, that's the completely and utterly most frustrating thing about shopping in the men's department for me, is the pant length thing... Still drives me crazy even in the women's section too though. But at least you don't have to spend hours saying, 'Where the heck am I going to find a freaking 36-30 pant?' (Using hubs' pants size as an example.  Kid you not, went to the consignment store... they had out of like 30ish pairs of size 36 pants, FOUR pairs that were 36-30... And two of them were grossly hideous that even my husband would have enough sense not to wear. [My husband has no sense of fashion whatsoever, so he just lets me and his mom shop for him hahaha... *gasp* Oh no! I have a sense of fashion and I dress my husband ... I can't be male... Or maybe I'm just gay... *eyeroll* Stereotypes... Am I right?])

But yes... I want to know who that genius is so I can give him a firm beating... Err... calmly explain that there are crap ton of body types, not just models.  You will find that in the women's department too.  Everything tends to cater to models, so even a size two regular pant often is made for a 5'6"-5'8" woman... Which is why I actually brought up the pant sizing point, to show that you're not entirely screwed when it comes to pant lengths.

Also, that's another thing I left out about women's clothes.  Most aren't sized like men's according to leg and waist size. And because they expect you to be model thin, your clothing size will probably be bigger than you expect.  I will have to try and find the waist size conversion chart that gave me a shock of my life when I realized my normal size when I'm not overweight is like an extra extra extra small in men's hahaha. (To give you a rough idea... Plus sizes for women start around size ten I think, and a 36 waist is a size twelve.  Size 6 pant is a 28 inch waist [that's what I'm shooting for within the next few months because I found my old jeans which are one of the few pairs that don't fall off my hips lol.  But my normal size is a 2 or a 4])

I'd have to second consignment / second hand stores, but since those aren't an option, I'd suggest Walmart online. Amazon is good too, but be sure to look at estimated delivery times before finishing an order - a lot of clothing items are actually shipping from China (despite claiming to be Prime!) and usually ship slow-boat (1 month or so delivery time). Be careful with sizes on Amazon clothes, too. They don't always tell you when they're Asian sizes (reviews will often reveal this, though).

Something else you'll discover about women's clothes (if you haven't already) - no two company's sizes are the same!  Wear size 10 Levis? Sorry, Wrangler 10's are too small! Same with tops, shoes, lingerie... pretty much everything. The trick is to find a brand you like and stick with them so you know the size will (/should) be consistent. I'm kind of in the middle between large & medium for tops, so It's always a shot in the dark for me unless I can try it on first.

As for makeup, watch some youtube videos for advice (there are a bunch by trans women - in fact, there are probably some about clothing, too now that I think about it!) first, so you have an idea of what you may need. I highly recommend the brand 'e.l.f.'. They are very cheap, but quite good (and not tested on animals). I love their foundation & blush, but I'm not 100% sold on their eye shadow just yet (need to pick up a couple more pallets to try out). Their basic synthetic brushes are only $1 each (you can pick up a set as a starter, if you don't know which ones to get). Be sure to get some makeup wipes, too (though you can get them from Walmart, too).

Quote from: Roll on September 06, 2017, 04:51:20 PM
I wish I could just go try stuff on, that would be amazing. Unfortunately, courage and acceptance aside, I am in probably one of the worst places you can be logistically for this sort of thing without being in a country town with a 3 digit population. Clothes shopping in general is a chore, as there are literally no stores that aren't overpriced boutique type places here, designed to rip off the super rich and tourists. (I'm on a resort-y/summer home centric barrier island off of Georgia, so actual stores and support for residents are slim. Takes a trek across a bridge just to even get within 15 minutes of anything, and I'm on the opposite end of the island of the bridge.)

I forgot to respond to this in my last response.  I totally know how that goes. Downtown Salt Lake and Park City (where ski resorts are generally located) are totally similarly messed up.  Though Salt Lake if you move out of the city center does get a fair amount better.  And like you said, its because they are the touristy areas and high class-y type areas. (But UofU is also right by downtown SLC so that also tends to be the reason SLC has a fair amount of options, as it is the most... liberal of the northern/western universities.) I live in a podunk town about 30 miles SW of Salt Lake, and its population is slowly growing (only became a city in 2010) and they are not so slowly urbanizing it, and not five minutes away we have all those boutiques and fancy restaurants. Drives me crazy that we have to drive through the chic city next door, almost to the other end to get to a walmart. (although really, I don't have many rights to complain... Utah cities really aren't that big. Driving from SLC to my town, 100 blocks, you pass through [if you take city roads not the freeway] six cities. Two of those cities being the biggest cities in Utah lol.)

Quote from: Sarah_P on September 06, 2017, 05:59:42 PM
I'd have to second consignment / second hand stores, but since those aren't an option, I'd suggest Walmart online. Amazon is good too, but be sure to look at estimated delivery times before finishing an order - a lot of clothing items are actually shipping from China (despite claiming to be Prime!) and usually ship slow-boat (1 month or so delivery time). Be careful with sizes on Amazon clothes, too. They don't always tell you when they're Asian sizes (reviews will often reveal this, though).

Something else you'll discover about women's clothes (if you haven't already) - no two company's sizes are the same!  Wear size 10 Levis? Sorry, Wrangler 10's are too small! Same with tops, shoes, lingerie... pretty much everything. The trick is to find a brand you like and stick with them so you know the size will (/should) be consistent. I'm kind of in the middle between large & medium for tops, so It's always a shot in the dark for me unless I can try it on first.

As for makeup, watch some youtube videos for advice (there are a bunch by trans women - in fact, there are probably some about clothing, too now that I think about it!) first, so you have an idea of what you may need. I highly recommend the brand 'e.l.f.'. They are very cheap, but quite good (and not tested on animals). I love their foundation & blush, but I'm not 100% sold on their eye shadow just yet (need to pick up a couple more pallets to try out). Their basic synthetic brushes are only $1 each (you can pick up a set as a starter, if you don't know which ones to get). Be sure to get some makeup wipes, too (though you can get them from Walmart, too).

I agree on the sizing being inconsistent with women's clothing haha! Having tried almost every brand of (American) denim jean there is for females trying to find ones that don't fall off my hips, I will GLADLY volunteer to help you compare whether things run big, small, or just fine.
Oh... another pants tip... Women's pants are made for hips.  So since you're still trying things out, (and I assume not gone through many physical changes) you're going to have fun keeping your pants up.  And another pro tip.  Female pants are not made for belts, and thus belts are purely decor pretty much. If you try and wear a belt to hold your pants up, you WILL have issues... I think it was Lucky brand and Aeropostale pants that I found were the straightest down pants.
If you want to wear skirts and dresses, I recommend for skirts maxi skirts as they are pretty much a straight cut (and generally a little cheaper from my experience). But overall, I'd go a dress route because they generally give you a waist and flow out from there, and don't curve back in. Skirts are more likely to 'frame the hips' and what not.
Of course, this is going under the assumption you are starting with 'stereotypical' male body with slim or no hips.

On makeup, my expertise is pretty limited, but I do know a few things if you need hypoallergenic makeup.  Clinique if you are willing to shell out the money is probably the best from what I've experienced.  Mary Kay claims to be hypoallergenic, but made my face burn like a... something.  I hate Estee Lauder. It always felt too heavy.  Sephora is fun, but not exactly the most friendly for sensitive faces.
BUUUT my all time favorite 'cheap stuff' is Neutrogena's makeup line.  GREAAAAAAAAAAT stuff.  I can't remember what I used for eyeshadow and eyeliner though... But almost everything else was neutrogena. I think my eye make up the last time I wore some was Almay or something? More than anything though eyemakeup is my worst enemy.  My eyes and cheekbones are where I react most.
And your makeup colors... While you're learning and watching all those thousands of makeup tutorials on youtube, I recommend using natural colors.  Not as easy to notice while you're learning the whole makeup routine. Plus sometimes less is more.

  That's really the most makeup I've ever liked to wear.
Vs.... my natural look


(Please note, these are from like 10 years ago, that's really the last time I wore makeup... [AND I don't take many pics] so take my makeup advice with a grain of salt.
And yes, I really don't smile in pictures.  I hope as I transition more that I'll see myself more in pictures soooo I'll smile more.)

I know that you can't get to brick & mortar stores easily.  But trying clothes on in a second-hand store is really the way to go.  So, although you will need to get some items online, take advantage of any opportunity you get to shop in real stores when you are off the island.  ( I lived on a small island for eight years.  Didn't even have a bridge, only a very expensive ferry, so I get it.)

If you get to a city a few times a year, make sure that you crawl all the second-hand clothing stores.  Some will sell junk, but sometimes you can find a gem of a store that has amazing, high-quality, fashionable clothes at really reasonable prices.  Just make sure you try everything on: second hand clothes might have shrunk or stretched from their alleged sizes.

Almost all my wardrobe came from second-hand or discount stores.  About the only thing I paid ful price for was underwear.  Cis women get an entire lifetime toy buid up their collection of clothes and establish their own style.  Trans woman have to do it in a relatively short time.  We don't necessarily have a style yet, so we have to experiment to learn what works.  I don't mind making fashion mistakes if they only cost me a few bucks.

Thank you all for the tips and help! I feel like everyone went above and beyond with these answers.

Walmart's online store was the answer to the cost issue, I already see a ton of things for rock bottom prices that are exactly what I want. (Which for now is a dress for sure, women's jeans just doesn't seem like enough of a change. )

Fortunately, I'm probably headed to Atlanta next year so that will alleviate issues when it comes time to shop for real. But I'm not willing to wait that long.

(And I definitely don't suffer from slender hips, even with no extra weight. Not sure if that is going to turn out to be a great thing or just a minefield for having to constantly keep weight off. I know for my mom it was a problem, but then while I have her build I have my dad's freakish farm-stock predisposition to easily building lean muscle and calorie burning. That's the only reason I wasn't more overweight as a guy, so maybe I'll get lucky and it will even out even on hormones.)

I'm glad

Quote from: Rowena_Ellenweorc on September 06, 2017, 07:55:27 PM

On makeup, my expertise is pretty limited, but I do know a few things if you need hypoallergenic makeup.

I'm so glad you said something, I hadn't even considered needing hypoallergenic. I have pretty bad psoriasis (sometimes I feel like I have everything) and considering scented and non-"sensitive skin" deodorants and detergents will set me off I'm sure makeup will probably do the same. (I am on Humira which takes care of the psoriasis enough that I forget I have it sometimes now, but it can still be easily triggered by the wrong thing. But hey, at least I'm used to injecting myself with a needle every two weeks already if that becomes necessary for HRT.)

Just took a huge leap forward psychologically and worked up the nerve to order some clothes off of Walmart's website along with a little bit of makeup(I never order from there so it won't be happened upon like an order from Amazon would, plus the price was right). Picked up what I thought was a cute dress, a cheap temporary wig (their selection sucks and is mostly Halloween oriented ), and some other little things. Praying it all fits, but if it not each item was under 10 dollars. I'm both incredibly excited a the thought of finally having something of my own as well as unbelievably terrified this will be the one time a family member opens my packages by mistake. (Though I suppose that would solve the coming out dilemma.)

I'm also completely terrified of what I'll look like, because I know it won't be a model. Not sure how to handle that other than just reminding myself I still have weight to lose, makeup techniques to learn, and years of HRT and other feminization to go.

Ohhh, do you own a car? How far is the nearest city? Do you ever go outside your island for things like Best buy (or to do shopping for Christmas)? Do you have maybe a Kohls or JCPenney outlet (or a similar place where you can order online, pick up and check the item and return in person)? How do you plan to explain a barrage of parcels coming to you before Thanksgiving? Wouldn't it be better to have a one trip 50-100 miles away and get everything bought in one shot?


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Quote from: elkie-t on September 15, 2017, 08:28:06 PM
Ohhh, do you own a car? How far is the nearest city? Do you ever go outside your island for things like Best buy (or to do shopping for Christmas)? Do you have maybe a Kohls or JCPenney outlet (or a similar place where you can order online, pick up and check the item and return in person)? How do you plan to explain a barrage of parcels coming to you before Thanksgiving? Wouldn't it be better to have a one trip 50-100 miles away and get everything bought in one shot?


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She is just starting out on the journey so she wants to see how it feels before fully committing.  Experiment so on, so forth. (Sorry Roll if you don't want to change your pronouns yet. Just let me know if you prefer something else!) I feel like taking a 50-100 miles away trip is better when she has fully settled and decided that the goal is to pass as a female in the future.
Course, this is just my thoughts, Roll can speak of course for herself.  (Sorry this came off as rude, I didn't intend it to be rude.)

Now, for my thoughts directed to Roll. I just want to say congratulations!  Hope this first step goes well, and that its hassle free. Here's to hoping you don't have to come out before you're ready, and here's to hoping everything fits well, and you figure out the makeup routine, and all that! And mostly, hope that you have fun with your new clothes.  You'll have to let us know how it all goes, how everything fits, and how the makeup is working for you. (I'm really curious on the last since you said that you have psoriasis.)

Good for you Roll! Don't be discouraged if the sizes are wrong (I think even with Walmart online you can exchange most items if they are!), or if you don't look perfect. I think very few of us looked very glamorous our first time dressing. This is something that takes experimenting - finding not only your sizes but also what cuts & colors look good on you. I'm still working on it myself! 

1 week is short. If all the nice clothes don't come just right, 2-3 days would be lost. Ordering online to house can be risky. Just saying... If a big mall is just 50 miles away, it's 1-2 hrs of a drive, I'd do it for fun and relax besides, the further from home, the less risk of an exposure. I am trying to offer the best practical advice for a good time that is fairly short - go to the nearest city, grab tons of dresses from Goodwill and Salvation Army, buy heels from Payless and whatever makeup you fancy from Walgreens or Target (I'd fancy Walgreens for a beginner), swallow your male pride and just do it safely far away

We all were beginners

If you can make a pilgrimage down to Jacksonville or up to Savanah each has a handful of Goodwill stores, and there are a few in between, too.  It might be an hour or more drive for you but you just can't beat shopping in a real store.  Of course you'll have to have the nerve to shop in the first place, that took me a half hour of hemming and hawing my first time.

Quote from: Rowena_Ellenweorc on September 15, 2017, 08:40:35 PM
She is just starting out on the journey so she wants to see how it feels before fully committing.  Experiment so on, so forth. (Sorry Roll if you don't want to change your pronouns yet. Just let me know if you prefer something else!) I feel like taking a 50-100 miles away trip is better when she has fully settled and decided that the goal is to pass as a female in the future.
Course, this is just my thoughts, Roll can speak of course for herself.  (Sorry this came off as rude, I didn't intend it to be rude.)

Didn't sound rude at all.

In this setting, I definitely prefer the she/her pronouns. I am used to them from years of MMOs with people assuming I was female already, so I have no adjustment necessary when it comes to online interaction. In person it's a different story, but I imagine that is pretty typical.

Any trip, much less 50-100 miles, is definitely beyond me though, both for some of the reasons you mention as well as simple logistics. I don't have a car, and believe it or not actually don't even have a license (actively working on that as well). My decade of self imposed exile due to anxiety and agoraphobia issues extended to driving in a big way and has been a major limiting factor.

Quote
Now, for my thoughts directed to Roll. I just want to say congratulations!  Hope this first step goes well, and that its hassle free. Here's to hoping you don't have to come out before you're ready, and here's to hoping everything fits well, and you figure out the makeup routine, and all that! And mostly, hope that you have fun with your new clothes.  You'll have to let us know how it all goes, how everything fits, and how the makeup is working for you. (I'm really curious on the last since you said that you have psoriasis.)

I didn't get anything too special makeup wise yet unfortunately, I wanted to do some more research before spending too much money. Just picked up some cheap lipstick and concealer which I have no idea what to do with or what else I need to make it come together at the moment. I didn't intend to get any at the moment, but wound up adding them originally just to break walmart's free shipping threshold.

Quote from: elkie-t on September 15, 2017, 08:28:06 PM
Ohhh, do you own a car? How far is the nearest city? Do you ever go outside your island for things like Best buy (or to do shopping for Christmas)? Do you have maybe a Kohls or JCPenney outlet (or a similar place where you can order online, pick up and check the item and return in person)? How do you plan to explain a barrage of parcels coming to you before Thanksgiving? Wouldn't it be better to have a one trip 50-100 miles away and get everything bought in one shot?

Setting aside the car issue, the nearest city is close but the bridge doesn't really exit near anything. It's then another 10-15 minutes out to get to Walmart or Target. I'm not completely isolated or anything, it is just extremely inconvenient. The larger issue is the quality of said city and that in general I don't expect it to be particularly "guy trying on woman's clothes" friendly. The island has a California-ish vibe, but the "city" is pure deep south.

The package barrage is actually normal around here, particularly as I don't drive it is how I get most things anyway. Not even just me, it's an online shopping household. The delivery guys all know us well.

Anyway, thank you all for the well wishes! I measured thoroughly and then compared myself to my sister and step mother's sizes for reference, so I think I ordered as close as possible for a first attempt.

Thrift/charity shops are still, to this day, my best friends, followed by the more expensive consignment shops. In thrift shops tops are 2-3 dollars in general, jeans about $5, about 3-5 for skirts and dresses 5-7. You can do a lot of experimenting on a budget.

The down side is the scary, somewhat loss of anonymity you may feel in say a big department store where you fade into the crowds. But as my wife once told me, My money is just as green as anyone elses and they are glad to take it. So fr she has been right. Even when I walk into the fitting room with a large armload of female atire in male mode I don't even think I got any odd looks.

TBH - I found it is best not to look for "odd looks". Life is far better that way.

Oh my god. Oh my freaking god.

So I just returned to the (ugh) real world after receiving my packages from Walmart. After they arrived I immediately ran to try everything on. Soooooooo yeah. I've never been so in love with something as the dress I now own.

I apparently nailed the sizes. Right off the bat that made me pretty happy. I was careful not to look at myself in a mirror until I got the full set on I ordered. A dress, some undergarments including control top hose, and a wig for now. So, a bit scared but not getting my hopes up, I went and looked at myself.

Even unshaven. Even with no makeup on. Even with balled socks not being a substitute for breasts (or even breastforms). Oh my god I actually looked pretty good. I need to lose more weight, I needed to not have beard stubble, I need the effects of HRT (socks and facial curves), I definitely needed to not have shoulder hair (oddly of all the packages, new hopefully more effective razor did not arrive), and I needed makeup... but I was still extraordinarily pleased with how I looked. Not just from a "whoa, I think I'll be able to pass if I wanted to" perspective, but I just... jesus, I just looked happier. When I went to put on the lipstick (only makeup for this trial), I was near delirious. Just that simple act validated everything I've felt thus far. The hose was definitely a good call, helped to shape some of the extra weight and lift butt a bit, but I know those are effects I can replicate naturally with diet and exercise. The wig felt fake (cheap halloween wig, so I was expecting that), but it definitely was integral to not breaking the "illusion"... But that dress just.. it was perfect. (https://www.walmart.com/ip/Tiffany-Grey-Women-s-Cold-Shoulder-V-Neck-Tie-Waist-Wrap-Dress/55837196) I am no longer the least bit worried about my shoulder width, I know that much. Didn't look the least bit wide, at least with that style dress and with the wig. Chest depth still a little bit of a concern, but not insurmountable.

To have something of my own, something that actually suits me (pure luck on this), something that is distinctly feminine, something that I feel so comfortable in... This is the feeling I've been looking for since I was 10. What was most amazing is how quickly it just felt right to the point I almost walked back downstairs with some of it still on, and actually did entirely forget about the lipstick for a bit but no one was home fortunately. (I imagine someone walking in with me just sitting there wearing lipstick. That one might have been hard to talk myself out of.)

Next... tackling makeup! (And resisting the urge to order more clothes.)