Wardrobe Overhaul for mid-30s 5'3 Trans Guy
Hey everyone! I've been on t for about a year and a half and am not rly passing yet. I don't think my ultimate goal is passing above all else, especially not at the expense of being flamboyant (I'm a pretty fruity bi guy and want to express that) but it would be nice if people didn't always ma'am me, you know? Would love suggestions on how to get started with this kind of style. I know nothing about male clothing sizes or how to find something that will fit my short, somewhat chubby body (175 pounds, mostly in stomach and hips). Open to any suggestions for clothes, brands, etc!
Edit: thanks for asking, price range is a little lower (budget is maybe $300-$500 total rn) so thrifting sounds like a good idea but am open to splurging on a key piece or two!

23 Replies
first off congrats on the T
that semi sheer lace embroidery in the top left was pretty popular last year w/ a lot of brands lol
missed out but there were a good number in the ~$150 range on ssense sale in july
Are you comfortable going out thrifting I feel like I say this to everyone but I swear I see tons of these shirts in various sizes at all price points
bottom right is straight up just a&f I think
not terribly helpful but i actually have a theory that the saint laurent menswear show in about 35 days is going to look a lot like this moodboard and im excited for that so you have good taste
also yeah drop a price range lol
Simone Rocha does a ton with these sort of uhhhh
ig slutty shirts but they're a hefty amount
When it comes to overhaul I think starting SLOW and with casual outfits (ie what you wear everyday/casually) is best because you'll wear it more and you'll find out what fits into your lifestyle and comfort zone. I agree that thrifting is a great start. also take a tape measure to stores/your current wardrobe and measure stuff that fits you the way you like - makes it easier to navigate sizing charts and online thrifting. So maybe start with 1-3 'new' items and see how you like them for a little while
My goal isn't to pass as male at all, but I definitely think I get he/himmed more when I'm wearing an open jacket of any kind (and if i'm not wearing a tight shirt lol) anything that creates a straight line along your sides will make a big difference. Having straight or wider pants will help continue that straight line. If you search me on the server you can look at my fits - i'm 5 6 and a cis woman with a medium-ish bust (i wear like a 30F) and similarly curvy hips and I think you can probably see what makes me look more or less masc.
When it comes to overhaul I think starting SLOW and with casual outfits (ie what you wear everyday/casually) is best because you'll wear it more and you'll find out what fits into your lifestyle and comfort zone. I agree that thrifting is a great start. also take a tape measure to stores/your current wardrobe and measure stuff that fits you the way you like - makes it easier to navigate sizing charts and online thrifting. So maybe start with 1-3 'new' items and see how you like them for a little whilei think this is great actionable advice from wonky! i also want to say take it slow, know your measurements and like ana said try thrifting if you're comfortable from this screenshot i can see a theme being high-waisted pants, bold patterns and drapey fabric. if you hone in on that rather than specific brands (esp when thrifting) i think it'll serve you well.
Thanks very much, all! Updated with price range π One additional q I have is on thrifting, I haven't done much of it before, how do you find a good place? I'm in NYC so I feel like there's a lot, where do I start?
Server GOAT charlie has a blog post about it https://backseatdriver.blog/2023/12/31/a-guide-to-menswear-shopping-in-nyc-for-2024/
Charlie Caulfield
Backseat Driver
A Guide to Menswear Shopping in NYC (updated 2024)
βIβm planning a trip to NYC next month. Itβs my first time in the city, and I want to go shopping while Iβm there. Where should I start?β This is a recurring question that has been postβ¦
the cool thing about most thrift (assuming you're in a big city is a lot of ppl are rly supportive and helpful)
DAMN this is a lifesaver ty!!
And there's lots of NYCers in the server! if you're looking for specific places, areas, etc, I'm sure folks can give you direction if you post the question in a separate q&a
my friends love urban jungle
in brooklyn
i still haven't fuckin been tho
soz
ahh I've actually heard of that! I think they got reviewed somewhere big recently?
oh did they
fuck
it may be joever
LMAO yeah like NY mag or something π
If you are willing to deal with the worlds worst UI and also know your measurements well Facebook marketplace becomes your best friend. UI is so bad that vintage resellers don't usually bother with it so there will be random gems that people are just trying to get rid of if you are willing to go pick it up in person.
I may be confusing them with another store tho....not sure
i can try to pull out the list my friend sent
i know also chelsea flea
honestly I would love that tia
https://maps.app.goo.gl/H68eVEnEYtSfmdoN8 here's a place she rec'd
Tokyo Joe NYC Β· 334 E 11th St, New York, NY 10003
Tokyo Joe NYC Β· 334 E 11th St, New York, NY 10003
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β Β· Consignment shop
also buffalo and second street