Return to blog home page

6 Men’s Winter Outfit Ideas Inspired by Celebrity Styles

January 12, 2021
Get ready – we've got men's winter outfit ideas you're going to love. (Source: Shutterstock / Dean Drobot)

Get ready – we’ve got men’s winter outfit ideas you’re going to love. (Source: Shutterstock / Dean Drobot)

Note: This post contains mentions of third-party brands whose offers are available on Grand Giraffe. We may receive a commission for purchases made from these brands.

The biting chill of winter is no longer around the corner – it’s here. But never fear, you can stay warm and sport some sizzling styles all through the winter months. To help, we’ve curated a handful of men’s winter outfit ideas that we think will spark some “oooo’s” from the fashion-conscious while keeping you totally toasty. And to inspire our list, we’ve called on celebrity styles that will really catch an eye.

1: The lumberjack’s flannel (inspired by Chris Evans)

This one comes courtesy of America’s Superhero, whose love affair with flannel never gets quite enough attention. But boy, does it deserve it. Pair it with a well-groomed beard and some cargo pants and you have almost guaranteed entry into the “top 10 rugged men of the year” list. We recommend getting your hearty flannel button-up with a semi-thick lining so you can stroll through winterscapes as easily as lounge at home. Columbia Sportswear has a few you might check out – with discounts that will make that lumberjack getup all the more affordable.

Flannel – so dreamy (Source: Shutterstock / El Nariz)

Flannel – so dreamy (Source: Shutterstock / El Nariz)

2: Woodman’s boots (inspired by Leo DiCaprio)

Remember “The Revenant”? Let’s call it Leo’s snow day – a chance for the starry-eyed dreamboat to get rough and tumble. And there was something ruggedly attractive about this Romeo. As far as men’s winter outfit ideas go, this one was a must: “Revenant”-style boots, rugged, durable, but ever-so-comfortable. Worn with a hooded wool parka, you could spend all day snowshoeing through the winter wild. Why, you might even stage your own version of “The Revenant.” (On second thought, don’t do that.) Oh, and it turns out we have some deals on boots at influenceu that would save you some bucks on this sole-warming footwear.

3: Hiker’s cords (inspired by Liam Neeson)

Okay, so in all fairness, this is more of a fall style – depending on what part of the country you’re in. But the cords so fashionably worn by the great Liam Neeson in “A Walk Among the Tombstones” was a sartorial win. He even pulled off a corduroy jacket – which is a style we thought we’d never see. But you know what? It works. Instead of going for wool pea coats and thick-cut jeans, consider a cord combination this winter – Lands’ End has some styles you might like.

The sweater-and-jeans idea really works for both urbanites and rural adventurers. (Source: Shutterstock / RossHelen)

The sweater-and-jeans idea really works for both urbanites and rural adventurers. (Source: Shutterstock / RossHelen)

4: City slicker’s jeans (inspired by Billy Crystal)

Didn’t see this one coming, did you? The inspiration here is actually not from “City Slickers” but from “When Harry Met Sally,” the beloved romance flick from the late ’80s (if you haven’t seen it, put it on your list). We’re actually quite taken with Billy’s sweater-and-jeans combo in the movie, and see this becoming vogue in the months ahead. Simple? Yes. Understated? Maybe. But that’s why we like it – and it’s warm enough to survive the winter months, provided you pick a cozy sweater. (Check Prps for deals on jeans, btw.)

5: Snug base layers (inspired by Robert Redford)

Who thinks of Robert Redford in tight-fitting shirts and ski gear? We do. While it may not mark the height of his career, “Downhill Racer” inspired us to sport more of those long john-y layers. These days, you can get them in performance spandex (not the suffocating cotton of yesteryear), so you remain warm without sweating. You can even wear a T-shirt or button-up over your johnnies without worrying about excess bulk. Heck, you could even wear with nothing on top but if you so choose, but be sure you pick a color that fits your design style. (Here’s a deal from U.S. Outdoor that gives you plenty of options.)

The perfect watch works for winter – but lasts for all seasons. (Source: Shutterstock / MS_studio)

The perfect watch works for winter – but lasts for all seasons. (Source: Shutterstock / MS_studio)

6: The adventurer’s watch (inspired by Sean Connery)

Rest in peace, super spy – and continue to inspire our confident fashions for every season. True, a watch is not a uniquely winter accessory, but it does add a touch of sophistication to the rugged men’s winter outfit ideas we’ve already mentioned. We recommend something that’s robust, but doesn’t glitter – and definitely includes plenty of gears, buttons, and knobs. Timepieces International has some with world times baked in, which is great if you happen to be an MI6 agent ever on the go. Or, if you just enjoy travel.

All in all, we’d cap our men’s winter outfit ideas with this piece of advice: No style is wrong, even if it’s not Hollywood-inspired. Just be consistent (ye rugged trekkers, stay rugged; you classy urbanites, stay classy) and make sure you’re as warm as you are stylish. It is winter, after all.