7 Chic Ways to Style Your Activewear in the Winter

Maybe the life of the legging isn’t over yet? These chic styling ideas prove your favorite comfy bottoms can look modern, intentional, and with these looks, nobody will ever suspect that the gym is part of your day. For this project, I grabbed my favorite pair of everyday black leggings and met my friend, Jamie Lewin, at Nordstrom (where they happen to be having a major winter sale right now). Jamie is the founder of the fashion publication Vetted Magazine and the perfect person to help me bring activewear to the next level. Don’t worry, I know when to call in the big guns.

Look 1: A Quarter Zip Pullover and an Oversized Men’s Blazer

This definitely was the funnest look to shop for— that’s because we took a trip to the men’s department of Nordstrom and the adorable older gentleman working there laughed when we told him we were shopping in his department for ourselves. But Jamie showed me that there truly is something so chic about an oversized men’s blazer on a woman. And it’s such an easy look to achieve by simply raiding your husband’s closet.

I asked the pros (Jamie), the key to styling a look with an oversized piece. You need to have balance in the whole look. So if you are going with an oversized blazer then the bottoms need to be tight fitting (and vice versa). So the legging is literally the perfect piece to pair with an oversized blazer.

How’d we do?

Faux fur is a must-have fashion accessory right now. The dressier fur top with the more casual legging bottom makes this look interesting and unexpected. We paired it with my tall boots to break up the leg.

Look 3: A Trench Coat (with just about anything)

I was about to say that this is my favorite look but honestly, they have all been my “favorite” so far. I guess it makes sense that I had so much fun with this project! This look was completely inspired by the beautiful and long trench coat that we happened to stumble upon on the sale rack. There is something so beautiful, cool and absolutely timeless about a trench coat, no matter what you are wearing under it.

I love the combo of the Chelsea boot, cool glasses and the oversized (again, menswear inspired) sweater I am wearing with my leggings. And yes, this great sweater is also on sale. Whoever said January wasn’t a good time to shop?!

This coat was the one thing I left Nordstrom with. I mean, how could I not? The sale price is $119!

Look 4: Track Pants with an Unexpected Top

This look breaks the rule of small on top and big on bottom with two oversized pieces, but I’m ok with it, and so was Jamie. I think these track pants work with so many different style tops in a very fashionable way. Here, we are styling the pants with a blazer, but a cashmere sweater is also a great way to elevate track pants.

But wait! How much fun is a sequin top with track pants? This look was all Jamie and she gave me the confidence to just go for it. Here are a few sequin tops that would pair great with the pants— a tank, sporty sequin, and I love this one (before I even knew it was on sale).

Look 5: Stirrup Leggings with Heels

The beauty of this look is the visible stirrup legging with the heel. It’s sexy and chic and takes a simple black legging to a whole other level. This stunning wool coat (you guessed it) that’s on sale and the funnel neck sweater that’s under $100 also add to the sheer beauty of this look.

And if you want to get really chic, don’t forget the hair tuck.

Look 6: Bomber Jacket with Capri Leggings

Talk about an it-girl look as you head to the gym. Simply throw on a fabulous crop bomber jacket and go. Bella Hadid is wearing a gorgeous leather bomber above with her capri leggings (that I have told you before are back in the most fashionable way). My coat below is an investment, but it’s a special piece, and one that I do think will also go on sale as the season goes on.

So have you picked up a pair of capris yet… or dug out your old ones? I love these.

If you want to go from the gym to the streets, a simple but stylish transition tip is to swap your leggings for leather pants. You can keep the sneakers and the crewneck fleece and be fashionably ready for whatever the day has in store for you.

Oh and a pop of faux fur is always appropriate!

Who knew activewear could be so chic, right? After Jamie gave me some inspiration, I realized that my most fashionable looks may actually come from my activewear drawer. We had a blast with this project and I’d love to bring Jamie in again. So let me know if you enjoyed this post and if we should style activewear like this again in the spring.

*All photos in this post are clickable. This post contains links that are commissionable for me, at no additional cost to you. Rest assure, I only write about products that I genuinely use and love, and that will never change!

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