Skip to main content

Introducing: The Rhythm of the Trouser

The Autumn Trousers Edit In Motion

Chicago Outfits

 87 products

Filter and Sort

87 products

Sort

View

87 products

We The Free Fable Low-Rise Twisted Bowed Jeans

£118.00

6 colours

More Inseams Available

Chelsea Funnel-Neck Jacket

£158.00

7 colours

We The Free Cute In This Cardi

£158.00

11 colours

We The Free Jamie Henley

£58.00

17 colours

We The Free Tennessee Low-Rise Boyfriend Jeans

We The Free Desert Moon Suede Jacket

Spotlight Washed Barrel Chino Trousers

We The Free Minimalist Moxie Barrel Jeans

We The Free Jude One-Piece

We The Free Opal Swing Denim Jacket

We The Free Onset Pull-On Cargo Pants

We The Free Stand Up Barrel Chino Pants

FP One Kaiden One-Piece

We The Free Good Luck Mid-Rise Barrel Jeans

Jojo Washed Oversized Funnel-Neck Jacket

We The Free Stand Up Barrel Chino Pants

We The Free Good Luck Barrel Dungarees

Nocturnal Patterned Cashmere Cardi

FP One Blake Thermal

Silverlake Wide-Leg Chino Trousers

All I Need Cozy Hooded Duster

Going Places Cardi

Jojo Washed Oversized Funnel-Neck Jacket

So Soft Seamless Modal Mock Neck

We The Free Alter Ego Wide-Leg Twisted Jeans

Barbour Laoise Check Quilted Jacket

Lex Pull-On Barrel Pants

We The Free Camden Sweatshirt

We The Free Love Me Not Bloomer Jeans

Chunky Marl Headband

Moonflower Balloon Trousers

Margot SoftSpun Sweater Tee

Cleona Harem Pants

We The Free Madison City Denim Jacket

We The Free Cute In This Cardi

See Me SoftSpun Pullover

FP One Blake Thermal

We The Free Atlas Dolman Tee

We The Free Dallas Distressed Suede Bag

Hailey Tweed Duster

So Soft Seamless Modal Long Sleeve

Spotlight Herringbone Barrel Trousers

We The Free Deep Trance Dropped Boyfriend Jeans

We The Free Dawson Pocket Thermal

We The Free The Cool Kid Suede Micro Shorts

Rainbow Run Hat + Glove Set

Wide Awake Layering Top

We The Free Don't Wait Up Pinstripe Boyfriend Jeans

Blaze Pull-On Boots

We The Free Farley Vegan Bomber Jacket

We The Free Everything Pullover

Julien Wide-Leg Chino Trousers

We The Free Latte Blues Solid Thermal

We The Free Risk Taker Mid-Rise Jeans

Roma Suede Tote Bag

We The Free On It Zip-Up Cardigan

Jojo Washed Oversized Funnel-Neck Jacket

Something Good Pull-On Barrel Pants

Marlo Pants

Hollis Sweater Midi Dress

Cordes Canvas Tote

We The Free Good Luck Mid-Rise Barrel Jeans

We The Free Good Luck Mid-Rise Barrel Jeans

We The Free Hattie Hardware Shoulder Bag

We The Free On It Zip-Up Cardigan

Lee Low-Slung Barrel Rider Jeans

See You Soon Studded Tote

Most Wanted Cardi

We The Free Roma Trouser Crop Jeans

We The Free Jude Shortalls

We The Free Jess Long Sleeve

We The Free Deep Trance Dropped Boyfriend Jeans

Outfits for Chicago

Get ready to turn heads in the Windy City with our curated collection of Chicago outfits! Whether you're exploring Millennium Park, catching a show at Second City, or enjoying deep-dish pizza, we've got you covered with versatile pieces that capture the city's vibrant spirit. Mix and match our effortlessly cool tops, bottoms, and accessories to create looks that transition seamlessly from day to night. Shop our Chicago outfits today.