5 Winter Outfits Worth Wearing

A Winter Outfit Lookbook

If you’re in need of a little winter outfit inspiration, you’ve come to the right place. Whether you’re dressing casually, in need of something for an evening out, or want to try something new, I’ve put together five of my best winter outfit ideas to help you out.

1. Business Casual

One of the things I always think is tough when it comes to winter outfits is dealing with outerwear. How many times have you built a great look around a piece of outerwear only to have it feel incomplete when said piece of outwear is removed? It’s a common occurrence this time of year. That’s why I fully endorse the sweater layered over button-up look. It’s practical, stylish, and looks complete and completely unfussy even without a coat.

Jacket (here and save 10% with code Brian10)
Sweater (here)
Gingham Shirt (here)
Cotton Pants (here)
Shoes (similar here)

2. Night Out

For an elegant evening winter outfit, always think simple. A cashmere turtleneck paired with some charcoal flannel pants is luxe, cozy, and sophisticated. Try tucking your turtleneck into your trousers to make things look neat and clean. And swap out your dress shoes for a nice pair of lace up dress boots for some hidden sartorial flair.

Jacket (here)
Turtleneck (similar here)
Pants (here)
Eyeglasses (old but search here)
Boots (here)

3. Stylishly Sporty

Here, we’ve got a pretty simple casual weekend outfit with a few subtle upgrades that really level it up. First, the classic quilted vest adds some visual interest. Next, if you look closely, you’ll see a subtle sartorial touch in the form of a scarf peeking out from under the vest. I always like to mix dressy and casual whenever possible. And finally, a wool baseball cap keeps it sporty and matches the season.

Wool Hat (here)
Quilted Vest (here)
Athletic Sweatshirt (here)
Jeans (here)
Scarf (similar)
Sneakers (here)

4. In-Between Layering

Shirt jackets are sort of these great in-between pieces. They’re kind of rugged but depending on how you style them you can kind of dress it up a bit as well. I tried to have it both ways here with the jeans and wool beanie more casual, and the denim shirt, layered sweater, and oxblood boots more dressy.

Shirt Jacket (here)
Sweater (similar here)
Denim Shirt (here)
Wool Hat (similar here)
Boots (here)

5. Winter Luxe

A winter color palette of tans, creams, and whites always projects some serious elegant sophistication. Very Ralph Lauren-esque, if you ask me. Ditto for a classic B-3 bomber jacket paired with a chunky turtleneck, white denim, and some suede chukkas.

Jacket (here and save 10% with code Brian10)
Turtleneck (here)
Jeans (similar here)
Chukkas (here)

Chime in: Which look was your favorite?

Thanks, as always, for reading.