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Style 5 Days 5 Ways

Long Live The Long-Sleeve Tee

5 ways to wear this casual wardrobe essential

by Gabi Updated: February 14, 2025

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In partnership with Huckberry

We talk a lot on Style Girlfriend about how good cold weather is for men’s style. A woman loves to see a guy who knows how to layer up, after all.

And when it comes to layered looks, there’s one piece of clothing every guy needs. A foundational element of casually stylish outfits. A men’s fashion lynchpin.

A long-sleeve t-shirt.

long-sleeve white t-shirt set against a blue background
shop the shirt: Flint and Tinder, $68 | Huckberry

After days of sub-freezing temperatures, you know what a day over 40 degrees calls for? A long-sleeve tee. Need something to wear under that elegant but itchy cardigan? Reach for a long sleeve t shirt. Want to breeze out the door but not in bare arms? You guessed it. Time for a long sleeve shirt you love.

What I especially love about this style from Flint & Tinder is its heavyweight, garment-dyed cotton, which gives it a nice drape and softness similar to the vintage tees of yore. 

This isn’t an undershirt that needs to be hidden away. There’s long underwear for that.

No, this is a shirt that wants to be seen. Even if it’s simply peeking out from a vest or shirt jacket.

It’s why a good long-sleeve t-shirt deserves a slot in every grown man’s wardrobe.

Treat yourself to a high quality style and you’ll find yourself wearing it all winter long. Dressing it up for a day at a casual office or dinner date. Or down with your favorite casual outfits (but without looking sloppy) on the weekends.

The tl;dr? A long-sleeve t-shirt is good for every guy in search of a light layer that sets him apart from the pack all winter long.

Below, discover 5 men’s outfits to wear with a long sleeve tee:

Monday
casual men's outfit with casual pants, a long-sleeve shirt, wool vest, and sneakers

Wear a long sleeve tshirt with a workwear vest

Shop the outfit:

  • long-sleeve shirt: Flint and Tinder
  • pants: Relwen
  • wool work vest: Filson
  • sneakers: Saucony
  • 6-panel hat: Huckberry

Winter date? A long-sleeve tee shirt under a wool vest gives you full range of movement and just enough warmth to not make you sweat. 

If the weather allows it, embrace the no-show sock—I don’t care what Gen Z says!—and flash some ankle.

If it’s too chilly, a wooly camp sock works just as well.

Tuesday
stylish men's outfit with a long sleeve t-shirt and sweater vest

Dress up a long sleeve men’s shirt with a sweater vest

Shop the outfit:

  • long-sleeve shirt: Flint and Tinder
  • athletic tapered pants: Flint and Tinder
  • sweater vest: Far Afield
  • chukka boots: Astorflex
  • beanie: Heimat
  • socks: Wythe New York

Want to dress your grey long sleeve shirt up? Just like your favorite short-sleeve tee, a long-sleeve tee works great under a sweater vest for a ’90s teen heartthrob kind of vibe (complimentary).

Chukkas and forest green chinos make a perfect fit for family gatherings where lots of food is involved.

This outfit would also look great with a pair of black jeans, keeping everything else the same.

Wednesday
casual men's cold weather outfit featuring grey sweatpants, a white long-sleeve shirt, and a quilted jacket

Wear a long sleeve t shirt with tailored sweats

Shop the outfit:

  • long-sleeve shirt: Flint and Tinder
  • “Après Pant” sweats: Taylor Stitch
  • quilted jacket: Relwen
  • sneakers: Asics
  • sunglasses: Sunski

Just because the weather outside is frightful, that doesn’t mean a casual outfit has to be!

Go for fashion and function with a long sleeve t-shirt paired back to stylish sweats. You’ll look and feel a little more put together.

Top it all off with a cool pair of sneaks and a quilted jacket.

Thursday
men's outfit with work pants, a black long sleeve t-shirt, flannel shirt and leather jacket

Wear a black long sleeve t shirt with a leather jacket

Shop the outfit:

  • long-sleeve shirt: Flint and Tinder
  • double-knee work pants: Proof
  • lined flannel shirt: Relwen
  • leather jacket: Schott
  • boots: Danner
  • socks: WORN

A long-sleeve tee is the perfect safety piece when trying a new-to-you item. The neckline works great with any cut of leather jacket and mellows out what could be a statement pant for you, like these reinforced work pants.

Friday
casual men's outfit with a long sleeve tee

Wear a long sleeve t shirt with jeans

Shop the outfit:

  • long-sleeve shirt: Flint and Tinder
  • Japanese stretch selvedge denim: Flint and Tinder
  • corduroy workshirt: Relwen
  • moc toe oxford shoes: Astorflex
  • polartized sunglasses: Raen Optics

Take your tee out to the holiday markets with your go-to jeans and a festive corduroy shirt. This look would also work for a get-together with pals like a white elephant exchange.

More stylish cold weather men’s outfit ideas from SG HQ:


Dress Up Any Winter Outfit with a Stylish Scarf

Which Jeans to Wear with Which Sneakers

5 Days, 5 Ways: Corduroy Pants

Autumn Outfits Inspired by Starbucks’ Pumpkin Spice Latte

Gabi

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.

More articles by Gabi

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