Now and then, the fashion set sinks its teeth into an outfit formula and won’t let go. A timeless white skirt with a little black top. Beachy flip-flops and big, baggy jeans. Currently, it’s a windbreaker jacket worn with anything vaguely boho-coded. A slip skirt, breezy silk pants, or a broderie anglaise Bermuda short—any relaxed, romantic piece that juxtaposes against the nylon track jacket you’d wear as armor against gale-force winds.
A windbreaker trend has been brewing since last spring, when luxury brands like Prada, Burberry, and Miu Miu styled weather-proof anoraks with sequin party dresses and micro-minis. It was fashion first introducing the idea that the best windbreaker outfits were those that flirted with a so wrong, it’s so right approach. We were to forget the jacket’s gorpcore associations and play with unexpected pairings instead.
Now, on the cusp of fall 2025, fashion folks have found their contrast of choice for the hard-working windbreaker: A blend of track star meets modern bohème—a woman who worships at the altar of Mary-Kate and Ashley Olsen and pays for a boutique gym membership (whether she actually goes and gets sweaty is another matter entirely).
The outfit template is unexpected, yes, but ubiquitous all the same. On the hunt for pre-New York Fashion Week outfit inspiration, I recently logged onto Pinterest, and my home page showed me three iterations of the same look: a tech-y windbreaker with a swath of lace peeking under the jacket’s hem and super slouchy, wide-leg trousers.
Capri pants are another popular element in the outfit trend sweeping the fashion circuit. In August, supermodel Elsa Hosk wore a waxy black windbreaker with a mini ivory lace slip, cropped leggings, and mesh Mary Jane flats—a quirky combination I'm now seeing replicated all over, from NYC's sidewalks to Copenhagen street style.
Like most recent, all-consuming trends, the origin of boho-slanted windbreaker outfits points to The Row’s Spring 2025 collection. There, the sisters styled their Jilly Jacket, a $9,500 hooded windbreaker made of black leather, with white wide-leg trousers and suede sneakers. The hem of a white tee and something light and gauzy peered out under the jacket’s drawstring hem, underlying layers that hinted at what the fashion world already knows: The Row woman contains multitudes.
The coveted luxury brand also makes an insulated nylon anorak, named the Althena, that tastemakers are partial to pairing with Leset’s satin trousers or Chloé’s balloon pants that look like Victorian-era bloomers.
On paper, with each piece separated, you wouldn’t think a boho-esque windbreaker outfit would go together—some would say even when it's assembled altogether it still doesn't. But there is a certain coolness to the contrast that makes the styling compelling. Tension is, after all, often the secret ingredient to a great outfit. Take, for instance, the wrong shoe theory, which has inspired thousands of fashion girls to pair riding boots with sheer skirts and kitten heels with track pants.
In the interest of good old-fashioned fashion journalism, I tried the outfit trend myself to see if I, too, could tap into the aura of an on-the-go Olsen twin. Ahead, here's how I styled the two windbreakers in my wardrobe, as well as more looks from fashion girls and designer runways to add to your fall fashion bank.
Dark and Stormy
This dark gray windbreaker from Uniqlo's collaboration with Lemaire has been the cornerstone of my fall jacket rotation for a handful of years now. Typically, I wear it with dark denim or a long column skirt, but these lace-trim satin shorts from J.Crew add a softness that's well-aligned with my free-spirited personal style. (My exact J.Crew shorts are on the verge of selling out, but Reformation sells a similar, albeit shorter, pair.) My Khaite knee-high boots (one of my first Big Adult Purchases) were a no-brainer shoe to go with the Bermuda short.
Copy Kallmeyer
In recent seasons, Daniella Kallmeyer has become the designer to know out of the NYC fashion scene. Her uncomplicated, minimal-but-never-boring clothing has that key element we all want when getting dressed: easy elegance. Personally, I haven't stopped thinking about this look from Kallmeyer's Pre-Spring 2025 collection: an ivory silk taffeta windbreaker with a liquid-like midi skirt and wrap-around sandals.
2025's Track Suit
No crushed velour needed—all you need to get the tracksuit effect in 2025 is a tech-y nylon jacket and lightweight loose trousers in a coordinating color. Add a pendant necklace to break up the tonal pairing, like Juju Vera's viral shell or something fringed and fun.
Level: Intermediate
With one boho windbreaker outfit under my belt, I felt confident enough to introduce a new challenger into the formula: a transitional fall sock. Using a blush-colored tencel bomber jacket from Exquise (the same brand responsible for last summer's viral Tobie dress) as the base, I added a vintage, lace-panel A-line skirt with lace panels (thrifted in Paris, sorry!), Madewell kitten heels, and baby pink Bobmas socks.
Pedal Pushing
A Dad-like khaki windbreaker and lacy tunic likely don't come first to mind when thinking about how to style capri pants, an already controversial silhouette with residual early-aughts cringe. Still, if your mind and heart are open, it ends up being a well-balanced combination with a soft sensitivity that aligns with the overarching boho revival.
Rainy Gray Days
Take inspiration from the sky you see on rainy days and use moody gray as the starting point. A smoke-colored windbreaker will be your anchor, while a black lace-trim slip skirt and silver metallic pumps will act as additional complements.
Take Tibi's Lead
If Amy Smilovic, creative director and founder of Tibi, is going to do one thing with her runway show, it's present ample styling tips that I'll want to steal and integrate into my everyday dress. This triple color combo from Tibi's Spring 2025, featuring a navy windbreaker, black bike shorts, and a chocolate brown clutch, is one of them.
When in Doubt, Go Sporty
Admittedly, not everyone will feel comfortable taking the nylon track jacket out of its sporty realm. To still dabble in the boho arena while keeping the look in your comfort zone, consider a simple wide-leg trouser that still gets at the free-spirited feeling and a very on-trend brown sneaker.
