Boots·6 min read

Everything I’m Including in My “It Girl” Fall Wardrobe, Courtesy of Free People

It’s boots season, baby.

Free People x Frye
Free People
October 23, 2026

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Fall is for pumpkins, spices, and boots. We don’t make the rules, but we’re happy to follow them. Especially when our friends at Free People worked with Frye to bring us gorgeous boots worthy of a pumpkin patch photo shoot. Frye was founded in 1863 and designed their first boot in 1888 — so, you could say they know what they're talking about. Below you’ll find three of our favorite styles, plus a few clothes and accessories to help them really shine. 

Boots

Frye Cindy Pull-On Boots

Frye

Cindy Pull-On Boots

Studded heeled boots we’d wear on a night out…

This fall, swap out your stilettos for these heeled boots, elevated with studs around the toe. They come in four autumnal hues that will go with nearly any denim wash or dress you already have hanging in your closet. Trust us.

Frye Colleen Mid Pull-On Boots

Frye

Colleen Mid Pull-On Boots

A pair of mid-calf boots…

Not all boots need to be knee-height, and this gorgeous pair of mid-calfs is proof. Their shorter shaft makes them a great option for pairing with maxi skirts, midi skirts, and all lengths in between. These are also easy to throw on with leggings and an oversized sweater for an ever-so-slightly Western vibe.

Frye Mustang 15L Boots

Frye

Mustang 15L Boots

Cowboy boots designed for the city…

These tall pointed boots might just be our favorite of the entire collab — just look at the slight sheen and cool, western-inspired snip toe. They're not overly "cowboy," so you can wear them for dinners, holiday get-togethers, and pretty much any other social event on your cal this fall. 

Clothes & Accessories

We The Free Baby Emerson Tote Bag

Free People

We the Free Baby Emerson Tote Bag

A shoulder bag that’s giving early 2010s celebrity style…

Back when dresses belonged over jeans and leggings went under skirts, the washed-and-worn leather handbag reigned supreme. This vintage-inspired We the Free iteration is our current obsession. It’s spacious, adjustable, and full of pockets. Now where are those paps? 

We The Free Good Luck Mid-Rise Barrel Jeans

Free People

We the Free Good Luck Mid-Rise Barrel Jeans

One of our favorite pairs of barrel jeans…

Free People introduced us to barrel jeans a while back, and years later, we’re still grateful. This mid-rise version is perfect for fall, since they’re easy to pair with tucked-in, form-fitting thermals, or will sit comfortably under a chunkier knit. The 15 colors don’t hurt either. 

FP One Blake Shrunken Crew Neck Thermal

Free People

FP One Blake Shrunken Crew Neck Thermal

A crewneck thermal you’ll want to show off…

When your base layer is as cute as this one, it deserves a moment in the spotlight. We love everything from its waffle texture to its rounded hemline and perfectly shrunken fit. It’s equal parts cozy and cool. 

Solstice Cashmere Pullover

Free People

Solstice Cashmere Pullover

A plush pullover we’ll be wearing well into January…

Cashmere never goes out of style, and neither does an oversized pullover. So what happens when you combine the two? This huggable, live-in-able Solstice top, that’s what. It has a slightly cropped, relaxed silhouette, which makes it ideal for layering over tanks, intimates, or PJs. 

Opal Rollneck Knit Sweater

Free People

Opal Rollneck Knit Sweater

Our go-to knit this season…

If you like knits that are boxy and roomy like crewneck sweatshirts, then you’ll love this chunky cotton knit. The neckline is more mockneck than rollneck, but it still gives you significant coverage. Go ahead and snag these in a few different colors. You won’t regret it. 

We The Free Good Luck Barrel Overalls

Free People

We the Free Good Luck Barrel Overalls

A different way to show off your knits…

A great way to fall-ify your denim overalls is by adding a knit sweater and any of those Frye boots above. We love this set of overalls for their iconic barrel leg shape and pre-worn feel. This season, we’re excited to sport the Port and Irish Clover colors. 

Opal Rollneck Knit Cardi

Free People

Opal Rollneck Knit Cardi

A knit cardi that has us reaching for our tea mug…

We call this one of our Coastal Grandmother staples because of its chunky cable-knit fabric, slouchy silhouette, and tortoiseshell buttons. You’ll catch us living in this cardigan by the fire, spicy read in hand.

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