Setting: Small office, all women, professional, but mostly business casual. Jeans are allowed, but not encouraged. The women in my office NEVER wear skirts or dresses, heels, or make-up. Two of them wear jeans most of the time, and more casual shirts. The boss dresses nice, always professional, slacks, low heeled shoes, minimal jewelry, minimal make-up. Nobody does nail polish. We've all worked together for over 5 years now. The ladies upstairs are more in the public eye, and do wear dresses, make-up, nails done, etc. The guys in management upstairs wear shirt and tie every day. The non-management guys upstairs wear button down shirts or polo shirts, no ties. I am seen by everyone in the office while I'm outside to smoke, and a couple times a month when I have to go upstairs for something.

I want to slowly transition away from my more feminine clothing, so they get used to it slowly. I can layer, since I'm always cold in the office. I tend to wear a coat or jacket all day inside because the office is so cold.  My lighter jacket and winter coat are fairly androgynous, but summer is coming. I think a man's jacket would be a bit too much at this point. But a men's sweater might work?

I have one pair of brown lace-up shoes that are passably masculine, and I love them, but I haven't been able to find a black shoe that works for me. I'm thinking I'll expand my search to slip-on styles, though I love the look of the oxford.

Aside from the really overweight woman, I have the biggest boobs in my office. The other 3 are all maybe an A cup (and I am profoundly jealous of them, lol) and approximately the same height and weight as me, which is 5'6" and up and thin.

I'm thinking to start wearing more button down long sleeves and long sleeved polos. I always push up or roll up the sleeves of my shirts, and gradually reduce the appearance of my more feminine, collarless, shirts.

Also, the overweight woman notices every single little change in my appearance and comments on it.

Advice, opinions, tips, and tricks, please!

Big YES vote on collared shirts.  To do it slowly it would probably be best to start with women's button downs; those were my favorite when I worked for a company in San Francisco.  Nice slacks and a button down always made me feel dressed up in a comfortable way, and both men and women wear such outfits.  Are you interested in binding?  Possibly start with a sports bra so it's not patently obvious to the coworker, and you can always claim "losing weight" if she presses you about it.  Even if she does comment, if you seem confident and happy about it and treat it like it's no big deal, most people will follow that lead.  Hope this helps, and good luck

I agree button downs are your friends. I started wearing those before I started T, actually you might think everyone is looking at you, but no one cares. I went from a more feminine (nothing extreme-- round neckline shirts and slacks) to dockers and button-downs and guy's pants. I only had one person comment on it (basically saying it suited me). I came out the last day to this guy who I had a friendly work relationship. He had no idea. I asked if he noticed my presentation. Nope. I said, "well I dress in a male way now." He didn't notice. Funny thing is that I dressed EXACTLY the same way he did, when I pointed that out he kind of laughed.

--Jay

I have 3 women's button down shirts I wear, untucked. I think my sports bra might show through 2 of them, so have not worn that combo at work yet. I'm a large B/small C, and men's small shirts fit me perfectly in the shoulders. If she says anything about my chest, I will just say the sports bra is so much more comfortable than regular ones (which they are). I've only worn the sports bra once, under a sweater, and still had my bulky coat on all day, so I don't think anyone noticed.

Btw, Jaydawg, you might want to post this question on the FB group.

--Jay

I've seen skin toned sports bras online...You could also wear men's A shirts underneath, white and black are usually acceptable to be seen-through under button downs in my understanding, though I've used skin colored A shirts too.

In my experience, even if people did notice they didn't comment. I went from dressing reasonably feminine - female button down shirts and dress pants, with the occasional dress (though never heels or makeup) to wearing pretty much exclusively men's shirts and slacks over the space of a couple months. The closest I got comments about it were "That's a new shirt?" and "That's a new look for you." Both of which could be brushed off with "Thanks, I'm trying something different."

I used to wear guy button down shirts, with a binder under it and guy dress pants, the only thing I kept feminine was my hair, I tried to style it in a more feminine way, I figured slowly, I could style it more manly, and the shoes, I wore flats, going to try guy dress shoes next time i'm in an office environment though, usually if you do it slowly, no one really cares long as the work gets done

I am in the very same stage where it is difficult to choose what to wear. But so far, the cold weather has been kind so I could sort of hide the fact I was wearing binders under my jumpers.

But the weather is certainly getting warmer so this is becoming difficult. I mostly wear buttoned shirts but I think I look a bit silly in them since even my binder can't hide my chest I feel it's a lot about finding the right balance between a tight shirt than a way too large a shirt that just won't work in an office.

I have found a few good chinos which make my life easier and I think you could easily pull them off at work. I will let you know if I find anything else that works well for me as I am also experimenting with clothes these days.

What I could say though is that if you have a good female friend/girlfriend/partner, they might be happy to help with that. I know it has become my girlfriend's biggest hobby these days...