It’s true what they say–what’s old is (almost always) new again. Especially when it comes to our tried-and-true favorites – flares.
Flare jeans are rooted in Free People’s DNA–it’s a mainstay silhouette that, at least to us (and Bella Hadid and Margot Robbie as of late), serves as the ultimate icon of effortless style. Flare jeans are timeless and are forever making their way back into the spotlight. They’re akin to a (very distinct) signature, a perfect blend of cool factor and a universally flattering shape.
And our favorite flare pairing? Boots–because they fill out the flare in all the right ways, giving your look shape without trying too hard. They create a flattering and elongated look, whether you go with a heeled boot for a dressier feel, or a chunky style for an edgier vibe.
Read on to see how our studio stylist, Maddie, is styling flares–and the shoes we’re wearing them with–this fall and winter season.
STYLING 101
How to Style Flare Jeans, the It Look for (the Rest of) 2025 (and Beyond)
By: Maddie Fressle
FP STYLING GUIDE: WHY WE LOVE FLARE JEANS
HOW TO WEAR OUR FAVORITE FP FLARE JEANS
OUTFIT #1–THE GREAT OUTDOORS
With the more rugged style of the West Coast flare, we love leaning into a heritage-esque layered vibe for this look–fun fall adds like a lightweight jacket and Western-themed accessories for choose-your-own-autumnal-adventures. With that in mind it feels very appropriate to pair with a stompier and substantial western boot.
OUTFIT #2–CITY FLAIR
The Double Knot Straight Bootcut is a slim flare jean perfect for a city dweller (or visitor!) to wear out and about. We love pairing with a pointier toe shape to really play on that cool city sensibility–going back to an easy tank top and oversized jacket feels super effortless and cool. Don’t forget a tote bag for your shopping.
OUTFIT #3–LATE NIGHTS
We love the paisley printed Aster Jacquard Flare Jeans for channeling a true vintage bohemian vibe. Feels like the perfect outfit for a GNO– pairing back to a feminine cami and fun fur jacket. Love the hint of shine from these pointed toe boots–so chic but still playful.
OUTFIT #4–ON TREND
Our tried-and-true Penny Pull-On Flares are the perfect silhouette for, among other things, a big hip belt. Playing with brown and black feels super modern and hits current street style appeal. We love pairing the Penny with heeled brown boots–they make the legs look miles long. And whether it’s a good or bad hair day, topping things off with a headscarf can dramatize an otherwise simple look.
OUTFIT #5–ISO COFFEE, AND FUN
The Eden Wide-Leg Flare Jeans are so roomy and comfortable that they’re our go-to jean for a morning coffee run. We love pairing them with a sleeker shoe shape like the Harmonica Western Boots to elevate the look. Since the Eden is a bit wider than the average flare there’s plenty of room to accommodate a taller shaft boot, too–they’re not just for minis/shorts! With the playful nature of the Eden, a little stripe on stripe feels like the perfect top pairing.
OUTFIT #6–TABLE FOR 4
This super wide flare, the Emre Flare Jean, is perfect for dinner and drinks with friends. Add a touch of shine with the Ashton Heeled Boot, and this look gives personality without taking away from the big bell bottom. Love adding an unexpected striped cardi and elevating it with the timelessly chic beret on top.
A FEW THOUGHTS ABOUT STYLING FLARES
Ultimately, flares–and how you wear them–is a highly personal take. Since they’re already making a statement, you might opt to go conservative on the rest of your look, keeping the flare the star of the show…OR go full-on wow with longer-length tops and embellished shoes.
We like to wear our flares just grazing the ground (if not puddling), but with the uncertainty of fall/winter weather, sometimes a shoe with a little height can be a huge advantage in keeping cuffs free of rain and snow.
But, as far as we’re concerned, flare jeans make for perfect work attire, any time of year.
We like to wear our flares just grazing the ground (if not puddling), but with the uncertainty of fall/winter weather, sometimes a shoe with a little height can be a huge advantage in keeping cuffs free of rain and snow.
But, as far as we’re concerned, flare jeans make for perfect work attire, any time of year.
MORE TO READ
9/26/25 | BEHIND THE SEAMS
Your Official FP Fall/Winter ‘25 Trend Report
Home Office’s most anticipated end-of-the-year outfitting ideas.
9/22/25 | IT’S IN THE BAG
We’re Bringing 2009’s Slouchy Bags Back
Here’s three of them to celebrate.
9/12/25 | INSPO 101
How We Put the FP in Boho
Staking our claim in all things creative spirit.