I love a good windbreaker. I couldn’t begin to tell you how many I own from sports teams like the Rams to straight-up technical jackets for the gym and workouts. When I saw they were trending for spring, I actually got kind of excited. Shortly thereafter, one outfit combination started to be everywhere, and I found myself consistently stopping on every single iteration. Doing a deeper dive into how people were styling windbreakers, it started to change everything I thought I knew about this jacket. It’s not just the jacket you grab when it’s 62 degrees, and I am running out the door for a workout. It’s showing up over silk skirts and lace-trimmed shorts now. People are wearing them with heels. Nothing is matchy-matchy, nothing is athletic below it. Nothing feels safe or normal about it, but I keep going back to look at it every time.

I honestly love that now there are so many different ways to style the millions of windbreakers I have lying around. So let’s get into it.

Where It Came From and Why It Keeps Coming Back

Believe it or not, the windbreaker started as a military jacket. Early 20th-century soldiers needed wind protection - it’s literally as unglamorous as it sounds. After WWII, when nylon became widely available, the surplus versions started showing up on civilians, of course, mostly men, who wanted something functional and didn’t have much else to go on. Eventually, in the 1970s, runners picked up the jacket because it was light and packable. But then the 1980s happened. Windbreakers suddenly became neon, oversized, and logo-forward sportswear. It became the uniform of the athletic person and, sure, the aspirational folk as well, in equal measure.

The ‘90s are where windbreakers coded themselves into the cultural lexicon. Hip-hop got hold of them and never let go. Adidas, Nike, and the whole sportswear aesthetic were everywhere, on everyone who mattered stylistically, and it read as cool in a way that had nothing to do with its original function. That’s when it stopped being a jacket you wore because of the weather or need; it was the jacket you wore to say something.

Then came the 2000s, the rise of athleisure, and the decade when windbreakers were just mostly worn to spin class. Fine, it had its moment. Fashion has cycles.

What’s different about right now is how women are driving what the windbreaker becomes for the first time. They aren’t styling it in a way it always has been styled - matched up, sporty with sneakers, and the implicit nod to utility. They’re putting it over silk, over lace, and over things that belong to a completely different world and not apologizing for it. The jacket that spent a century being practical, functional, and let’s be honest, masculine, is getting paired with kitten heels, and nobody looks confused by it now.

I think that’s actually interesting. Not because it’s subversive in some big cultural statement way - it’s a jacket - but because it suggests the styling conversation around it has finally opened up. It doesn’t mean anything specific anymore. You can put it on with whatever you want, and the outfit decides what it is. That’s a relatively recent development. I’m into it.

Get the Look

Trendy + Feminine

Windbreaker + Lace Trim Shorts + Heels

This is the outfit you’ve seen everywhere lately, and I have to admit I’m not bored with it - yet. The Reformation jacket has a high-neck and is fitted through the waist, which is a great contrast to the lace-trimmed satin shorts. The combination makes no obvious sense, but that’s entirely the point. Once you’ve committed to that level of clash, every other choice needs to lean more feminine. The ankle strap pumps, the Prada Petit Sac Noir mini bucket bag, because nothing near lace shorts should read gym-adjacent, Miu Miu sunglasses, and a single Shashi statement ring. The jacket is doing one thing while everything else is doing the opposite, but nobody argues with it.

The Elevated Layer

Oversized Parka + Silk Midi Skirt + Kitten Heels

Nobody talks about the oversized parka enough, but this Mango one is 100. It’s 100% cotton, oversized, and has a high neck. Not only does it have a detachable hood, which honestly adds a really cool look to it, but it also has an elasticized waist. It looks far more expensive than it is. Paired with Reformation’s silk skirt, you get volume and movement, which is what this entire styling idea is built on. Plus, the Carolina skirt has that lace on the bottom trend that is everywhere right now.

The kitten heels in a light color are intentional because everything else is already so interesting; there is no reason to go dark. Of course, the Saint Laurent oval sunglasses and Miu Miu raffia top-handle bag are here. Those are two pieces I love right now. Finally, the Lie Studio drop earrings were chosen because this jacket covers up so much of your neck; they have that bit of glitz near the face to break it up. This is the lunch-that-turns-into-a-gallery-that-turns-into-drinks outfit. You know the one…

The investment build

Prada Re-Nylon Jacket + Flowy Skirt + Wedge Sandal

This one is expensive, but I think it’s worth it, and I’ll just leave it at that. The Prada Re-Nylon blouson is made from regenerated ocean plastic, carries the enamel triangle at the chest, and will still be in your closet being worn when every other windbreaker trend is long gone.

Adding a flowy skirt, in this case by Malene Birger, adds movement against the structure of the Re-Nylon that is pretty satisfying. The STAUD wedges add a little height that doesn’t compete while also pulling in yet another hot thing to wear right now. Finally, the Marcel tote by The Row is really the only bag that gives the quiet touch needed, while the single bar chain stud and bracelet add a little elegance without yelling too much. The whole look reads as effortless, even if it’s not.

Shop Windbreakers

The Bottom Line

I didn’t expect to be this invested in styling a jacket I’ve worn a million times and spent most of my life associating with sports, and yet here we are. I can’t wait to try all my jackets in new styling combinations.

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