When you're no longer handsome and the suit jackets just aren't working anymore.

[Evelyn K]

Yes, I know I'm becoming fat...

Emily I actually don't know your status, are you fully transitioning?

[Just Ole Me]

Gosh, I wish I had that jacket here... I will try to snap some full size pics today with decent camera and lighting. The suit matters just as much as what You wear under it.
You can even pull that look with sports coats as well - as long as they are not oversized, ofc.

This is how I roll everyday outside of the office

Ummm. Looks like a girl in guy clothes to me. Looking good!

[Evelyn K]

Emily - you look fem. And you know I ain't one to lie!

[TerriT]

My boy clothes don't fit me anymore and I refuse to buy any new ones. Today I actually moved a bunch of them into a different closet for storage. i only wear flannels and hoodies anymore in boy mode. All dress clothes are not practical any longer.

The thing though is that I really worked hard to have a fashionable wardrobe that was very much on the andro side. It's sad to have to let that go but it does feel affirming that I am moving past that stage. I do think about what will survive and I just can't let go of my killer pea coats and some jackets. But I have to keep making room for my new clothes. It feels different to purge my boy clothes for a change.

[JamesG]

I am trying to work them in together, the older male clothes that still fit and new stuff that is either male cut but more colorful and textured or female cut but of subtle androgy.  My sense of style and the look I'm going for is rather conservative and practical (butch) so that helps.  Also I'm a packrat when it comes to clothes, I still have pants and shirts from the '90s.

This is how I roll everyday outside of the office

You look a lot like my lesbian former neighbor. That is a compliment.   

[JamesG]

I think she might be transman, or could/would be.  So its like you two have passed in the middle.

[Evelyn K]

Yeah you look clean cut and very andro. The problem with me is my collar bone hair length. It tends to look sloppy in mens attire unless I sweep it all around my neck to one side.

[Evelyn K]

Have You tried to go for male ponytail and a couple of bobby pins here and there - if Your office policy allows this? Or You could always go for that extremity when You wash Your hair, condition it and dryblow everything backwards and then apply styling wax/gel in rich amounts to fix it... I personally hate it, but it might look better on other people.

P.S. And I am jealous of Your hair

Can't you grow yours out?

On the office front, I run my own gig in my place so I don't have restrictions. But it's the odd meetings with clients where I'll need to look professional. I've never tested appearing unisex-professional (no tie), not sure how I would be interpreted when a contract is on the line.

I can't do that waxed look. No way.

This will be an unanswered question for me I guess. For awhile. And so the experimenting continues...

[Evelyn K]

Emily is that a 16" chain in your new avatar? I would go with something a little thinner in thickness and an 18" chain. The reason is because I want the V shape of the chain to hang downwards a little longer to balance the length of your face. It will balance what I call the "ice cream on top of the sugar cone effect" better. Like as it is, it's too ice cream top heavy. you know what I mean? yeah sounds weird... And a little thinner because you want it to gracefully accent you, and not be too bold. That's what I try to do when wearing necklaces.

[Evelyn K]

I am working on it - if it would not be so slow... lol.

How long have you been trying to grow it? Like as it is now?

[Stella Stanhope]

I tried putting my hair up in guy mode and donned on a very handsome charcoal Kenneth Cole blazer, Kenneth Cole slacks and a white Hugo Boss dress shirt. I haven't worn this outfit since last Sept when I remember looking good with just a medium-long mens business haircut.

What I saw instead resembled a child. Rounded cheeks, wider eyes, softer glowy face. I absolutely could not believe how much I've changed. The jacket and dress shirt was totally incongruous to my soft features. And with my hair down draped onto the collar, what I saw was something that wasn't quite a gal, but not masculine either. I can only describe it as something in between, and innocent - and I felt attractive. The outright masculine clothes however just doesn't seem fitting anymore. The sport coats, blazers, the timberland's all of that stuff. It would seriously appear as if I can't dress well if I decided to keep wearing them.

You know what I mean?

That sounds awesome. And I wish I could hit that aforementioned "sweet spot of androgyny" too. I took have enjoyed wearing men's suits, back in the day sometimes bulking them up with two pairs of trousers, or thicker shirts to make me appear more muscular. I occasionally like to wear 70's and 80's men's stuff (because I love those decades and TV shows like Life on Mars and Ashes to Ashes). There are things I already feel sad for leaving behind, but there's also more I want to accomplish, and this will take moving even further in other direction to achieve. Pros and cons, etc.