Men's Style Inspiration  / Winter Style  / Men’s Casual Winter Fashion Made Easy

Men’s Casual Winter Fashion Made Easy

Your winter weekends just got so much better thanks to these casual outfits.

Men's winter boots
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After a week of hard work, you finally have a few days off to relax and enjoy the weekend. And though it may be cold outside, there are so many fun activities specific to the season. Ahead, we’re sharing four of our favorite things to do and our go-to casual men’s winter outfits to wear while doing them. These looks are perfect for the weekend, but work just as well on weekdays, too.

Check out a live show

While you can go to the theatre any time of year, there’s something special about going when it’s cold out. A relaxed outfit with polished elements is appropriate for the occasion.

  1. Start with a slim-fit turtleneck sweater and style it with coordinating straight-leg chino pants.
  2. Sleek boots add a nice touch, especially if they’re constructed from suede. But if it’s wet out, skip them in lieu of winter boots instead.
  3. Add a structured coat and patterned scarf to give your outfit the perfect layer of warmth and style.
Men’s sophisticated weekend outfit
Men’s ice skating outfit

Show off your ice skating skills

Whether you’re a pro or not, this winter staple can be enjoyed by all. It’s important to dress in a comfortable outfit that’ll keep you warm whether you’re on the ice or hanging out on the side.

  1. A wool knit henley worn under a classic sweater will help ward off cold chills without any added bulk.
  2. Choose a pair of slim-fit denim with a stretchy construction to allow you to move freely.
  3. Then make sure to bring a scarf and gloves—the gloves will come in handy for protecting your fingers if you take a fall.

Enjoy fireside relaxation

There are few things as relaxing as the sound of a rustling fire with a hot toddy in hand, surrounded by your favorite people. Go ahead and unwind with a comfortable look that can be worn for a casual dinner and beyond.

  1. When it comes to warmth and style, a fleece-lined jacket is our favorite. Look for a streamlined silhouette that’ll flatter your physique and a unique color to make the outfit pop.
  2. You’ll want sturdy footwear, like plain-toe boots with a durable rubber tread to give you traction when walking on slippery surfaces.
  3. Bring a beanie along to keep your head warm and to avoid having to style your hair. 
Men’s ski lodge outfit
Men’s road trip outfit

Go on a road trip

If you’ve got a case of cabin fever thanks to winter, then it might be time to hit the road for a weekend escape. Get the snacks and playlists ready, and we’ll show you how to put together an easy outfit for your trip.

  1. A crewneck sweater made from a soft fabric is a must-have. Go with a slightly oversized fit so you can wear a shirt underneath for added warmth.
  2. If you’re worried about your winter outerwear being too restricting, try a puffer vest instead. The sleeveless design will allow you to move comfortably.
  3. Waterproof boots not only gives the outfit rugged appeal, but it’ll also keep you prepared for the elements.
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