7 Easy Winter Outfits for Men for Office, Date Night, and Travel

It’s too easy to set a resolution to dress better but continue wearing the same old, ill-fitting clothes all year. Your resolution needs to have an attainable goal. We thought of it like this: January is when you should be purchasing wardrobe building blocks you can rely on all year, so why not make the resolution to buy one new outfit and wear it to death all winter. Make it your new signature. That can mean any combination of Vuori pants, Carhartt tees, Hoka sneakers, or (if 2025 was kind to you) something more luxury.

Below, we’ve done some of the work for you and created seven foolproof winter outfits that pair together our favorite pieces. They’ll never steer you wrong.

The Cold-Weather White Tee and Jeans

You should consider a white tee and Levi’s 505 your default casual outfit, no matter the time of year. Pedro Pascal’s waxed Flint and Tinder jacket makes a nice layer during the colder months. When it’s frigid, it’s your mid-layer, and as it warms up, it’s your outer layer.

An Easy Office Outfit

Boss man tightening those work from home restrictions? We feel you. Post-Covid office dressing is both a blessing and a curse—you’re trapped by a want to be casual, but obligated to look a little presentable. Since this is Esquire, we’d love for you to wear a suit; it solves all problems. But realistically we know that won’t happen. The only rule is this: no fucking shorts.

If you’re aiming for less than a full suit, our editors’ go-to Lacoste polo shirt and Lululemon ABC Pants can be mixed and matched with professional and casual pieces alike, including each other. Buy multiple color options, so your daily outfit dilemma can finally be put to rest.

Layering Around a Crewneck

Commerce editor Luke Guillory’s favorite Buck Mason Seafarer sweater makes a worthy splurge this winter. “It looks like a vintage sweater because Buck Mason, as a company, is obsessed with the quality of old clothes,” he writes. “It’s slightly shortened for a more classic, more flattering fit.” Corduroys, penny loafers, and wayfarers nod to heritage while maintaining a modern feel.

Elevated Athleisure

A matching Vuori jacket and Sunday Performance Joggers looks less Euro-gangster than an Adidas tracksuit and more put together than matching sweats. Did you just leave the gym? Did you just leave Whole Foods? A Tumi gym bag and Hoka sneakers will keep everyone guessing.

The Heritage Boot

We showed a made in the U.S.A. boot in our first outfit, but here we’ll make it the star of the show. “For guys getting into boots, these U.S.A.-made classic boots are a perennial favorite,” we wrote of the Wolverine’s 1000 Mile. “They make a casual outfit feel put-together in just about any environment.” Particularly when heritage wool and cashmere are involved.

Going Monochrome With a Fleece

Every man needs a nice sweatshirt in his repertoire—one that doesn’t have any sports logos or mystery stains. Per entertainment journalist Eric Fransisco, Todd Snyder’s Portuguese Terry Crewneck works for every casual occasion. As for building an outfit, we like to add a tonal fleece for a fun elevated casual sort of thing.

The Quarter-Zip Sweater

Even we are not immune to TikTok. To call quarter-zip sweaters a trend is somewhat laughable. The practical silhouette remains perennially in style; it’s simply experiencing a new wave of fans this year. Paired with Vuori pants, this well-fitting knit from Tommy Hilfiger wouldn’t look too shabby on a date.