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
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
Get Suspended
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
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
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.
