So today I bought my first girl clothes, Bikini bottoms, and I was wondering if any experienced crossdressers remembered their first time and/or had tips for crossdressers trying to buy some. I sneaked mine home in a box of Cheez-Its. Most crossdressers start off wearing sisters or their mothers clothes but eventually they have to buy their own. This proves especially difficult for closeted dressers.

The first time I ever bought any of my own clothes, I went to a Salvation Army store around Halloween. I told the salesgirl that I was going to a costume party, and she was very helpful finding me things. The undergarments I got from a K-Mart that was a short distance away once I had made all my purchases from that Salvation Army. The cosmetics I tried at that time came from a dollar store.

Now I get a lot of my clothes, and especially my heels, from Craigslist. It is amazing the expensive pumps you can get for relatively cheap that have only been worn maybe once or twice, or if at all sometimes. Hope this helps.

If you act confident, like buying women's clothes is something you do all the time, it makes it easier. If you act embarrassed or guilty, they'll know you are buying it for yourself.  If you act confident, they won't suspect, and will assume you are buying it for your wife or girlfriend.

I did my early shopping on Ebay. People in stores don't seem to care what you're buying, though.

Hugs, Devlyn

I don't exactly call myself a crossdresser - although technically you could kinda say I'm partially doing it now. Right now I'm only wearing women's jeans (skinny ones) (not other women's apparel because
1) it's hard to find
2) I wear them as I wear my other jeans (without feeling I'm "crossdressing" or anything)

(just crossdressing probably makes me more depressed)

When I bought my first girl jeans I was so fidgety being in the women's department. I kept looking and looking trying to keep my cool but it was so uncomfortable. Gradually though after many visits in stores I feel a lot more calmer and have learned to pick better sizes. In the beginning I bought sizes too large cause I was afraid it would feel too tight around the "cough" area but now I've found some that look way nicer (although they are tight).

(Now I feel like "yeah I'm wearing girl jeans, so what? I just like how they outline my legs)

Obviously for other items (shoes) I'll have to buy them online.

Quote from: Hayleytaylor on September 21, 2015, 08:08:44 PM
So today I bought my first girl clothes, Bikini bottoms, and I was wondering if any experienced crossdressers remembered their first time and/or had tips for crossdressers trying to buy some. I sneaked mine home in a box of Cheez-Its. Most crossdressers start off wearing sisters or their mothers clothes but eventually they have to buy their own. This proves especially difficult for closeted dressers.

My first skirt was my wife's. It was about 12 years ago. She wore it when she was at her 20s and the waist size was 27 inch. Initially I wore women's short pants, and later I purchased my own skirts at Salvation Army's thrift store. In a year, I started to purchase brand-new skirts. My wife picked up this one for me:



I went to my work place while wearing my first new skirt, causing some fuss, and I also was somewhat embarrassed.

Confidence is the most critical whatever you wear.

barbie~~

I've been crossdressing for years, and have my own account with VS, and other female sites. I do some local shopping, and yes, confidence is the key, I really don't care when the sales person stares, is startled because I want to look at panties( which I have an obsession for! ) . I find much nicer sexy, cute clothing on line, the trick is the fit. I wear size small panties, 38A/B bras, and usually the fit is ok, but each brand varies a bit. Shoes are tougher for me, I'm getting better with that also. Make it fun, and do not let the public shame you, it's your life, dress to feel great!


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Girl, that really brings back memories of some awkward and painful moments - and a few that are sort of funny.  I do remember once steeling up my courage to go into a "foundations" store in Houston.  A very nice matronly lady asked me if she could help me.  Of course I used that old ploy - that I was buying a gift for my wife.  And of course, my wife was about my size.  She was so complementary that I was making such a considerate purchase for my wife and helped me pick out a very high quality all-in-one that was waaaay over my price range.  But I was in love with it so made my purchase.  I nearly ran for the door convinced that I had pulled off my deception but on the way out the door she said, "Thank you Darlin' I am sure you will look lovely.  Come back soon."   I did and I am sure her retirement was a little bit richer for it.   

Now its almost entirely internet purchase.  Not because I am afraid to shop but I like the convenience and endless variety.  Life is simpler, but maybe a little less exciting??

Buy your lingerie online ! ! ! Head to JoAnne's or similar and buy a tape measure. Figure out what size you are.

When you purchase a bra, the "diameter" of the size measures the diameter of the chest AND THE MAMMARIES. And so if your chest measures 42, a size 42 bra is not going to work for you. You need to add for breasts. Jog bras stretch in the cup area, but still you need to allow a diameter in the garment that will fit around you.

Thrift stores just plain don't care what you look at or  buy. (No store does.) Locally, they are fine with my trying stuff in the fitting room. No issues. My mom owned a boutique, hand-crafted women's fashion. I learned what I know about clothing from mom. Women are generally amazed what I know about clothing -- fabric, color, style, details, construction, etc.

Mom also taught me to "Look at everything. Shop for everyone!" -- I've used the "cover" that I'm shopping for a costume wardrobe for the community theater group.

I don't do "high fashion" -- just not enough social situations where I can wear "dress up" clothing. Mostly I'm doing "recreational casual" at the beach. That said, the pink, dotted Swiss bridesmaid gown in MY SIZE for a few bucks was not to be passed up! Lot's of stuff like this, and it's liberating for both me and the sales staff at the shop to understand that these things are for ME, not someone else.

And so they pretty much compliment me on my good taste, my style, my eye for fashion. Women get enthusiastic about clothes. If you're up to speed and engaged in what you're looking at, that enthusiasm is mostly shared by women who share your interest in fashion.

Buy your lingerie online ! ! !

I suppose it's probably necessary to note that I "present" as "cis-M" but pretty obviously "trans something" -- and entirely "out" about it -- assertively "out" about it all.

Well my wife at the time helped me pick out clothes at first. It was a rush to know she supported my cd side. She even picked out my wig and makeup. The first time she made me up and we went out, i was so excited that i actually had a wet spot in my panties!

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I had stolen all my clothes from a friend's sister and family members before I ever bought anything. I think the first thing that I bought was a bra from the BX on an Air Force Base. I tried to play it off like it was for someone else and I had to begrudgingly buy it.

I buy a lot of my bras on eBay, concentrating on used garments in the "auction" section. I find that the brassieres are generally in new condition and very cheap. Often the mailing cost is more than what I pay for the bra itself. Sometimes I can buy 5 assorted bras for a few Dollars.

I can experiment with makes, sizes, styles, colours etc. at little cost. For example, I think I may now need an increased cup size, so I have just bid for a bra in the next size up. If it fits, I can buy more, if not, it can go to the charity bin.

Another reason for on line buying is that very often I find that a bra which seems to fit initially is not so good longer term. My favourite lingerie is often stuff which seems tight or uncomfortable to start with. Bras which you try on in the shop don't allow you a break-in period of wear.

When in the lingerie shop dressed as a man, I find it pays to be bold. If the sales lady approaches when I am looking at the bras, I ask perhaps "are the straps long enough for multi-way wear?" Sometimes a conversation then begins where I discuss my requirements openly, and the lady attempts to advise as if I were a woman.

Quote from: Kanda Jo on September 29, 2015, 12:42:55 PM
I had stolen all my clothes from a friend's sister and family members before I ever bought anything. I think the first thing that I bought was a bra from the BX on an Air Force Base. I tried to play it off like it was for someone else and I had to begrudgingly buy it.

WAY more fun to note, "I'm gonna keep the receipt. I can return it if it doesn't fit me?"

Thrift shop right behind the WiFi here has "all clothes 50% off" -- Their stuff is priced $1, $3, $5. $5 for sport coats, dresses, skirts, pants. $3 for blouses, T's, Tanks. $1 ties, bras, panties . . .

50% OFF -- and so fifty cents for panties. I found 6 pair NEW, never worn, size 10, nylon "granny pants" beige, blue, white. Nicely full cut.

T's and tanks -- nylon, cotton, trimmed, plain, striped, solids . . . some long sleeve, some w/ buttons/zips

Some tops (Kirkland / CostCo) are stretch Spandex w/ spaghetti straps and built in "bra" -- a variation on the "tube top" . . . These are nice "under-dressing" . . .

Couple blouses, polar fleece pull-overs, hooded sweatshirts . . .

This is day-in, day-out casual wear at the beach. Gender's edge stuff -- I'm most comfortable somewhere in the middle, between cis-M and cis-F. Not presenting "gender ambiguous" but rather, "border crossing" on a lot of socio-cultural planes.

I suppose we need to get over the idea that it's "some sort of costume."

We can "pass" as cis-F at a distance, but no social contact in public. Day in, day out we wear across gender lines, present as "cis M" more or less, but pretty out in the middle.

Out in the middle is no costume.

My first time I think I went to a Walmart or something like that and just picked out some simple clothes like skirts and dresses and that was it. When I was a small kid I would always try on my sisters clothes like her panties and tights and things like that and as I got older she moved out and everything was suppressed and then it would surface every couple of years.

I remember working at a Kohls and would unload the trucks that would come in and they have different clothes and I remember being a little thief and stealing panties and other clothing and taking them home and trying them on.

Over the years the feelings go up and down and I am now to the point where I am confident to just go shopping on my own in a store and buy what I want to buy and I don't care what the clerk says anymore. If it comes to being looked at wrongly I will just play it off as I am buying them for my make believe wife.

Congrats by the way! Everything is baby steps

Quote from: Allison Wunderland on September 30, 2015, 01:43:17 PM
WAY more fun to note, "I'm gonna keep the receipt. I can return it if it doesn't fit me?"

Thrift shop right behind the WiFi here has "all clothes 50% off" -- Their stuff is priced $1, $3, $5. $5 for sport coats, dresses, skirts, pants. $3 for blouses, T's, Tanks. $1 ties, bras, panties . . .

I would not recommend thrift shops, as I have a bad memory.

About 10 years ago, I purchased a pair of tight jeans. After wearing them occasionally, I got some skin disease in my buttocks, which has lasted until now. Used clothes stored in humid environment are a good hotbed for germs. Be careful.

barbie~~

barbie~~

Quote from: barbie on September 30, 2015, 04:22:57 PM
I would not recommend thrift shops, as I have a bad memory.

About 10 years ago, I purchased a pair of tight jeans. After wearing them occasionally, I got some skin disease in my buttocks, which has lasted until now. Used clothes stored in humid environment are a good hotbed for germs. Be careful.

barbie~~

barbie~~

Lots of stuff in thrifts is NEW -- cleared from retail inventory. Health Dept. in this state requires cleaning, washing clothes before resale. But sure, pay attention!

I wash everything before wearing. In new clothes it washes out sizing (starch) from mfg. Used, wash to disinfect, freshen fragrance

Ouch Barbie - thats rough.   

An alternative to thrift shops would be consignment shops.  The prices may be a bit higher but the merchandise is often of better quality, better cared for and more current fashion-wise.   The simple difference between a thrift and a consignment shop is that in thrift shops, the merchandise is owned by the shop and priced to move.  In a consignment shop, a clothing owner essentially contracts with the shop owner  to sell the clothing.  The proceeds from the sale are split.   In a consignment arrangement, the clothing owner has a lot of incentive to make sure the clothing is in good condition.    I have had good success in both types of shops.

Mom & 2 partners had a boutique, consignment hand sewn original, new. That's where I learned.

And mom taught me shopping for clothes, in thrifts. "Look at everything. Shop for everyone." No one cares what you look at. Thrift locally encourage fitting rooms, no problemo. Cis-F curious why I know what I see. I'm open about it being for me, and share stuff I can't make work but they can. "Ohh hey! Absurd on me! Stunning on you! Don't pass on this! LMAO" -- or, "I can't wear it, but I'm taking it home anyway!"

But I pull silk ties, and linen sportcoats too . . . candles, tools, jewelry, kitchenware, bags, duffels . . .

I buy all my stuff from thrift stores...I wash everything immediately, but now I think I'll wash it in HOT water!

I remember being super nervous the 1st time I bought some pantyhose from a grocery store.  I was out of town and just went for it.  Tried to act cool, but probably wasn't outwardly.  Online shopping works for many things, but nothing beats shopping with a friend or loved one.  My wife is supportive and selects things she thinks I'd look good in.  She also says "nope" to things she doesn't like and I respect that.

You can always get a box at a UPS store and get packaged delivered there so you can sneak them home if you aren't out to your parents yet.