Nikki’s Inbox: Easing Your Way Through a Stylish Transition from Female to Male

Hi Nikki, I’m a trans-guy who is having trouble finding things to wear. I’m currently taking a gap year, but I still want to keep up my nerdy, intellectual image of a college student since I always take a long time to get cool clothes and I want to be on par with my peers. My body type is slim-ish, as I wear 31-32 size men’s pants, I’m 5’8, 139lbs., and my chest size is 34D. (I do own a chest binder, so this isn’t as much of a challenge for me as it seems.) But I do have larger thighs that make it hard to find men’s pants that fit.

Coming from wearing “feminine” clothes for most of my life, I don’t really know what to wear to look masculine with my figure. I am open to wearing some women’s clothes, as I own cute socks and 1 skirt to show them off, but it’s not high on my priority list since I don’t go out in public dressed like that often (I like mori fashion and elegant stuff, though). I mainly want clothes that will look smart. (Maybe a little cute too? I’m a gentle person and not particularly edgy). I like sweaters and button-down shirts, and if it’s a formal occasion, I do have a few vests, but I don’t know what to wear other than that so I have a lot of t-shirts and some cargo shorts.

Also, I’ve been wearing dark colours over the past few years due to me feeling ashamed of my body and being depressed, so having some light clothes would be a nice change of pace. I like any shade of blue, but also silver, maroon, green, and grey, and I’m very pale so gem tones (except for yellows and oranges) look good on me, but I’d like to avoid pink. Any advice you have would make me very happy!

Rae, 18/USA


I’m probably the least credible authority on fashion for trans people but I really appreciate emails from them like yours, Rae. I’ve answered several over the years and while I really have no idea if the advice worked for those readers, I hope some of my suggestions will be useful for you.

A Good Fit Where It’s Needed: Shoulders, Arms and Chest

The ideal masculine shape is said to be an inverse triangle — wider shoulders tapering to a narrow waist and hips. For most women, that just means the top half of an hourglass shape. If you’ve just started your transition, Rae, then the silhouette you’re aiming for temporarily is a boxy silhouette. (Tip: YesStyle’s Womenswear carries a bigger selection of outerwear, including boxy cardigans So don’t rule out shopping in the women’s department just yet!) That means your shoulder width should be more or less the same as your hips. Men’s button-downs are good pieces to have in your closet, so 10 points to Gryffindor! Just make sure that they fit you where it counts: shoulders, arms and chest. The same rule applies for other structured pieces like blazers, jackets and coats, as well as your sweaters, hoodies and other tops. I’m not a fan of oversized fashion so the only compromise is to go one or two sizes up if those dimensions don’t fit. But wearing something overall sacky? Say no.

Save for the hair, the first outfit is something that ANYONE can wear.
Envy Look : Evzen : STYLEBYYAM

Choose Prints and Patterns Carefully

A binder definitely helps streamline your silhouette, Rae, so I’m glad you already have that. Even with a binder though, sometimes your natural silhouette can still be obvious so choose patterns and prints with care. While I personally like stripes, there are times when I prefer to be less conspicuous about my curves so if they are right on my chest, that outfit is definitely not for me. Non-linear and asymmetrical patterns may work better for you to avoid any telltale bumps or curves.

GERIO : HEIZE : Antszone : Bay Go Mall

Since we’re now heading into fall and winter, lumberjack plaid fashion will be skyrocketing. Big squares and big pockets will make you bigger, and not always masculine. So stick to smaller squares, smaller patterns, and more tastefully-sized details. Consider leather or metallic tipping at the collar, differently colored sleeves for sweatshirts, and epaulettes with silver- or gold-tone buttons too for a hint of military sophistication.

Color It Cool

Jewel tones pair well with the mori palette and are definitely great for fall and winter as well so I’m glad you like those colors, Rae. Gray is the new black so feel free to pair any of your favorite shades with that neutral. Gray itself comes in a myriad of shades and tints so the combinations are endless. Throw in a hint of metallic or a pop of contrast like a cranberry red scarf to go with a hunter green sweater and gray pants to keep everything interesting. And for the yellows and oranges that you don’t really prefer? Well, mustard yellow actually looks good with purple or burgundy. But if you don’t want to wear two strong colors at the same time, let the other one be an accessory. A mustard yellow or camel leather satchel looks truly preppy with khaki flat-front trousers and a burgundy sweater over a charcoal gray shirt.

Y!SHIER : Streetstar : JOGUNSHOP : Streetstar

Slim and Shady Pants

Rae, I will commiserate with you about how difficult it is to find pants that fit the thighs. While I’m sadly not blessed in the height department unlike you, I’m very gifted in the thighs and hips. I have to resort to buying jeans one or two sizes up to accommodate them and belts are definitely essential. However, if you’re rather bulky in the thighs but not in the hips and waist, why not go for a slim-straight cut? These jeans are less wide at the hips and thighs. You get a fitted but not baggy look and still with a fluid, long-line silhouette. Even with a bigger waist size, chances are the pants will still fit you well, and you can always wear your shirts untucked or wear a knit vest or sweater on top to hide the waist. And remember, dark-rinse jeans are very forgiving (they hide stains!) and work with almost anything! For trousers, flat-front pants are best but do take note of how the pockets are designed. If they’re cut at the sides near or parallel to your hips, they might gape. Choose pants with pockets that constructed similar to those in jeans.

JOGUNSHOP : Hey! DUDE : Superstar.i : Quincy King

I hope that as you go through your transition, you’ll be more comfortable with your new body and more confident about yourself, Rae. I still have a lot to learn about gender dysphoria so do let me know. If there are any Ask Nikki! readers out there with helpful advice for Rae, please post your tips in the comments. Let’s help each other!

P.S. If you’re sending a question, please don’t forget to include any helpful information about your body type or shape, your tastes or personality. You can include a selfie (link only please) or a photo of your clothes (which I will never publish without pre-approval). Thank you!

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