4 Masculine-of-Center Looks for Any Kind of Winter Date

Hello everyone! It’s me, AC — your Brown, non-binary, petite, genderfull fashion friend! First off, congratulations on surviving the longest January of all time.

On that note, I’m back to help you out with some masculine of center looks for a winter date night. Whether you’re taking out yourself, your friends, or a crush, you’ll need to put clothes on your body — ideally cute ones — which can seem like a whole situation especially during the colder months. So! Here are four warm and handsome outfit ideas, including guides on where to get my (or similar!) pieces, and tips for turning wardrobe staples into fabulous date looks.

Go with Your Uniform

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Everyone has their fail-safe outfit; mine is a plaid flannel and my favorite pants that I always feel good in, and that’s super practical for the cold.

Ideal for a trip to the movies, an arcade-themed bar, or for a lovely winter walk in the park, followed by a shared cup of hot cocoa. Also doubles as a Brawny man Halloween costume.

Get the look: Hat / Shirt / Straight-Size Jeans / Plus-Size Jeans / Boots

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Get Suspended

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Suspenders are my secret weapon to easily dressing up a date outfit (old-timey newsie is one of my many aesthetics). You can buy them new, or often find them secondhand in any thrift store’s “Mens” department. Bonus: Suspenders keep anxious hands busy.

We start here with fun colored pants and a microfloral button up, which is a usual work outfit for me. In order to change it up on the way to my date, I can add on the suspenders (matched to my oxfords) and pow — it’s a new outfit!

Get the look: Suspenders / Shirt / Pants / Shoes

Suit Up

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The suit: a classic! Perfect for a gallery opening, dinner at a fancy restaurant owned by a judge on Chopped, literally anywhere in order to use the smooth line, “This old thing? I just had to wear this for work.”

“But AC,” you protest, “I don’t have a suit!” Ah, yes friend! Neither did I, until I was working with fancy lawyers. Don’t fret; just find any blazer that feels amazing on you, trade in some dark jeans for slacks, and ta-da, you have a very smart outfit!

Underneath, I like to swap out a buttoned shirt for a turtleneck in the cold winter months. Don’t hesitate to play with colors and textures — not just with your jacket and pants, but also with your shirt, shoes, and socks. Think: rich maroons, forest green, velvet, corduroy. The world is your winter oyster!

Get the look: Straight-Size Jacket / Plus-Size Jacket / Straight-Size Pants / Plus-Size Pants / Turtleneck / Socks / Shoes

Tie It Up with a Cardigan

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Much like their suspender friends, adding a tie to anything makes it extra fancy — ergo, a suspender/tie combo will instantly elevate any day look. Wear to a dine-in movie theater, meeting the parents, or a fun lecture.

If you need an extra layer but your suit jacket feels a little too formal, top it off with a shawl cardigan. Here, I matched my tie to my cardigan (again, these add-ons are a great way to explore fun wintry colors and textures). Finished off with black ankle boots, this outfit makes me feel like dancing. I hope it does for you, too!

Get the look: Cardigan / Shirt / Tie / Straight-Size Jeans / Plus-Size Jeans / Boots

So, those are my winter date style tips. Now have fun, play safe, and be your own date before you’re anyone else’s! Catch you next time, cuties.

AC Dumlao is a queer trans non-binary genderqueer neurodivergent first-generation Filipino-American intersectional artist and advocate. They love (in no particular order): Beyoncé, Food Network, musical theatre, and 2000s boy bands. Follow AC’s genderqueer fashion/radical self care Instagram adventures.

AC has written 2 articles for us.

14 Comments

  1. Sort of personal question—are you wearing a binder in the shot with the suspenders? We have similar frames and I haven’t overcome self-consciousness about my chest area when wearing suspenders. Love the color and width of the ones your wearing and seriously considering purchasing them.

  2. Hi Cherilyn! I am not wearing a binder in that photo. I believe I am only wearing 1 sports bra. Sometimes I wear 2 sports bras with a nude tank top for when I want to appear flatter for certain outfits. (Also, additional Trans Parent PSA that any binding should always be done safely!)

    I appreciate you sharing your journey of working through self-consciousness — I totally hear you and empathize.

    Let me know if you end up buying the suspenders :) I have them in navy also (pic here: https://www.instagram.com/p/BKgGd_4AoLQ/?taken-by=menswearselfcare).

    xo AC

  3. I used to be anti-cardigan, but I got a cardigan sweater-vest one Christmas from my mother and when I tried it like a good child I felt like I was both Mr. Rogers and getting a hug at the same time.
    So naturally I kept it and began a side quest for a dark red full on cardigan sweater which I miraculously found on a discount rack while trying replace an item that died.

    Y’all cardigans(real ones with the collar and pocket not those tiny sweater set things from the 50’s) are great.
    You’ll feel real cozy like you’re in a hoodie or getting a warm hug, but are in fact fancy.

    And you can get them at like Target, it’s pretty cheap and cozy for fancy respectable clothes. Walmart has some too but they’re the thinner kind with no collar for the most part.

    Suit jackets are sharp yeah but getting one that fits right is harder/more costly than a sweater depending on your body dimensions.
    So consider the cardigan.

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