#OOTD: How to Wear a Crewneck Sweatshirt for Winter

Make no bones about it, folks: The new year is, as we’ve been saying, the best time to take stock of the men’s style essentials you can’t live without, and how you can make ’em all work for you in one seamless and stylish #OOTD. That’s where today’s main attraction comes into play: The Todd Snyder + Champion Crewneck Sweatshirt, a seemingly simple piece that’s as versatile as you make it. And believe me, you can make it plenty versatile when it comes time to brush up on how to wear a crewneck sweatshirt for winter. Life is still plenty casual for most of us, so this look is going to pull lots of duty this season, from Zoom calls to layered park strolls and the occasional to-go brewery outing. That’s why you’ll see it paired with other classic men’s style picks that you probably already have in your wardrobe, from a rugged quilted jacket to a timeless Oxford shirt. It all comes together in an ideal mix of classic looks, just enough cool style and plenty of functionality for blustery winter weather. If you live in a more temperate climate than your Brooklyn-based style writer, you can ditch the top two layers and wear the Buck Mason Oxford shirt as is. Any way you slice it, this look is as solid as it gets for a new year and a new you (or just an improved and more stylish you). Check out my Instagram account to see how I’m getting dressed in style this season with pieces much like the below.

A classic crewneck sweatshirt is just what the doctor ordered as far as winter layering.

  • The Sweatshirt: Todd Snyder + Champion Crewneck Sweatshirt, $98 — Here it is, one of the best crewneck sweatshirts for men on the market, if not the best. An undisputed *champion* when it comes to winter layering, folks.
  • The Jacket: Relwen Windzip Jacket, $258 — Stay warm in style with this rugged quilted jacket, an ideal casual-yet-versatile layer atop your Todd Snyder crewneck.
  • The Shirt: Buck Mason Classic Oxford Shirt, $95 — This timeless Oxford shirt for men is a stone-cold classic — unbutton the collar and roll up the sleeves for a bit of laidback, devil-may-care style this winter.
  • The Chinos: Taylor Stitch Slim Chinos in Organic British Khaki, $98 — It’s official: You’re keeping this outfit rolling the right way with a pair of the very best chinos for men, and that’s all there is to it.
  • The Chukka Boots: Red Wing Heritage Weekender Chukkas Boots, $219 — These classic leather chukka boots are a hot seller, and for good reason. They’re also the best chukka boots you can wear with this versatile, everyday outfit.
  • The Watch: Timex Chronograph Leather Strap Watch, $139 — This crisp, laidback-yet-sharp Timex leather watch is a highly affordable timepiece to pick up and wear as often as you can.
  • The Socks: Dozy Sleepy Waffle Socks, $38 — Don’t skimp on the details, especially when it comes time to take off your chukka boots. These well-made men’s socks from Huckberry are the right way to go.
  • The Everyday Carry: Filson Medium Rugged Twill Field Bag, $350 — For all the EDC essentials you need these days, get this tough Filson tote bag, then use it for years and years to come.

That’s going to wrap up today’s versatile and ready #OOTD. It blends the best of the best when it comes to both basics (like those comfortable and cool Dozy Sleepy Waffle Socks) with, of course, the ultimate centerpiece: The Todd Snyder + Champion Crewneck Sweatshirt,  as ideal a crewneck sweatshirt as you’re apt to find these days. And when you layer it up with an iconic Oxford shirt for men, you’ve got the makings of a business casual, Zoom-ready outfit or a casual weekend ensemble in equal measure. The two real keys here are the rugged quilted jacket as a top layer (a jacket that’s more than ready for winter excursions), as well as your classic Taylor Stitch chinos for even more go-anywhere style. Toss on a pair of classic leather chukka boots to keep that stylish versatility and rugged appeal rolling right along, then accessorize accordingly with a Timex leather watch. And whether it’s a day trip or a safe return to the office, your EDC essentials are safe and sound (in style!) with a rugged and aptly named Filson tote bag. The next time you need an all-day outfit, look to these gear picks, my friends. See you out there!

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