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best winter outfits menswear
best winter outfits menswear

Your Best Winter Outfit Ideas

January 14th, 2021

10 awesome looks from the HSS community

We received 100s of submissions for our call to be featured in the most recent video highlighting your best winter outfit ideas. To say it was difficult to pare it down to just 40 would be an understatement. It was even harder to choose 10 favorites from that list, but there were some gentlemen who really stood out to me and who I wanted to feature here.

1. a.gentlemansworld

best winter outfits menswear

You can’t beat a good belted safari jacket. Especially one in a winter-weight with a subtle herringbone. An excellent combination of earth tones here and I’d like to particularly highlight the hunter green turtleneck.

2. V.D.

best winter outfits menswear

There’s something about a Prince of Wales check flannel sport coat that just says “winter”, isn’t there? A very elegant and classic–but modern–look. White trousers are a very unexpected (in a refreshing way) winter choice. But the real hero piece here is the wonderful mustard yellow turtleneck.

3. Nash

best winter outfits menswear

This photo really made my day when it came in. Never mind the perfectly put together outfit here–big shout out for the chunky cable knit cardigan–because what this really shows is that a great smile can take an outfit from great to exceptional.

4. Johan

best winter outfits menswear

A perfectly-executed classic winter suited outfit. Grey flannel suit. Two-inch cuff. Double-breasted waistcoat. And a statement coat with some simple pattern mixing via the tie. What else can you say?

5. Long

best winter outfits menswear

Not everyone can pull off a suit like this with an effortlessness and confidence that we see on display here. And while the suit certainly stands out, it’s the winter white mock neck sweater that steals the show, in my opinion.

6. Thomas

best winter outfits menswear

A wonderful “elevated casual” look here. A nice mix of dressy and casual elements with the camel coat, white jeans, and hunter green shirt. Footwear choice is absolutely perfect for the overall vibe of this look.

7. Jean

best winter outfits menswear

Here, we’ve got a masterclass in the classic “menswear uniform”. Navy jacket. Grey flannel trousers. Burgundy patterned tie. Subtle complementary pocket square. And a nice touch with the button-down collar and wider candy stripe of the shirt.

8. Eric

best winter outfits menswear

I’m not sure if this is what I call a “Hollywood” flannel or light grey fresco suit. But, nevertheless, it’s a color that is super classic and really harkens back to a golden age of men’s style. (And not to mention that it’s a color that not everyone can pull off.) Everything about this look is perfectly executed. The burgundy tie with the subtle pattern is the cherry on top.

9. Chris

best winter outfits menswear

Another excellent take on the classic menswear uniform–this one with a bit more of a preppy feel. A great Prince of Wales check jacket, OCBD, and perfect club-style tie. While a light grey flannel pant might be the “obvious” choice, I’ve got to give props for the biscuit color here.

10. Adam

best winter outfits menswear

Never overlook a chunky shawl collar cardigan as a comfy alternative to a suit jacket or sport coat. It’s a great way to show some casual sophistication and paired with a turtleneck–even better. I particularly love the addition of the pocket square to bring that point home!

Which look was your favorite?

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Videography by Rob McIver

Video Editing by Ian Johnston


If you’ve been a fan of HSS for a while now, you know that I really love watches-especially nice watches. But it wasn’t like the first watch I ever owned or watches that I’ve had throughout my life have always been luxury watches.

Getting into and appreciating watches and developing and refining my taste in watches is something that has been a very long journey. And you’re going to find out how I eventually found myself walking into the Rolex boutique on Fifth Avenue in New York City with a pocket full of cash ready to buy my first luxury watch--a Rolex Datejust.