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Our Favorite Off-Duty Looks From Free People

Our Favorite Off-Duty Looks from Free People
Design: theSkimm | Images: Free People
September 8, 2025

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Figuring out what to wear when you're off the clock can be surprisingly hard. What's on-trend but still comfortable? Are loungewear sets worth the price? What even is boho-chic? We needed answers. So we started tapping our friends at Free People for effortlessly stylish (yet comfortable) looks, and we’ve never felt trendier. Back by popular demand, here’s everything we’re loving from Free People this season, from cozy transitional tops to leather accessories you’re sure to get compliments on. 

Looking for more affordable, stylish clothes? Here’s what to wear when working, traveling, and playing — and picks for your kids, too. 

We The Free Emerson Tote Bag
Free People

A leather tote that’s perfectly slouchy…

We’ve always loved We The Free’s vintage-inspired Emerson Tote, and this year we’re all about its mini version. It has the same lived-in look that gets better with use and is about half the size. Fill it with your current read, essentials, and extra phone charger, and have yourself a day. ($178)

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We The Free Moxie Pull-On Barrel Jeans
Free People

Barrel jeans our editor still raves about…

No matter what season, these pull-on barrel jeans will take any jeans-and-a-cute-top outfit to the next level. Pair them with a solid tank and sneakers for a laidback look or heeled booties for a night out. The pant legs taper in at the ankle so you can show off your footwear. ($148+)

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Alma Kitten Heels
Free People

Kitten heel boots we know will sell out…

These are certified Cool Girl™ leather boots. From the kitten heel and pointed toe, to the slim belt that sits around the ankle, these will be our most-reached-for boots by the end of the year. Get them before they're gone. ($258

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Intimately Dynamic Duo Tee
Free People

A going out top that’s actually cozy…

No need to freeze for your right to party. This stretchy, ribbed long-sleeve top has an ultra-wide neckline to show off your statement jewelry or favorite scarf, and is long enough to tuck into pants or a skirt. And who doesn’t love a little lace detailing? ($58)  

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Prairie Field Top
Free People

A top that takes us back to Tomato Girl Summer…

In case you’re not quite ready to let go of sundresses, this milkmaid-style top is a great transitional piece. We love both floral prints (in seasonally appropriate color palettes) and appreciate the stretchy smocked back for comfort. Add a suede jacket for cooler nights. ($98

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Bright Side Set
Free People

A breezy set you can mix and match…

Boho is back, and this top-and-skirt set is the first addition to our revived collection from 2016. To nail the latest iteration of the trend, layer a tank under this set and add chunky mixed-metal or beaded jewelry. The tiered skirt and top are also great for mixing and matching. Swap the top for a denim vest, or replace the skirt with a pair of jeans and tall boots for an autumnal look. ($168

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We The Free Hallie Plaid Shirt
Free People

A plaid button-down you’ll live in through winter…

Nothing gets us more excited for fall than a cozy plaid shirt. We love this one for its oversized fit, warm tones, and large front pocket. It’s a great top layer for running out to grab the mail, or for those WFH days when putting on real clothes is simply not an option. ($148

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We The Free Tennessee Low-Rise Illusions Jeans
Free People

The coolest low-rise jeans — if you’re into that sort of thing…

We don’t style-shame here, so for anyone who’s Team Low-Rise, we proudly present these iconic jeans designed to sit on your hip. The paint-splattered denim is one-of-a-kind, though you’ll be surprised by how versatile these pants actually are. They tend to run small, so be sure to size up. ($198)

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Intimately Fiona Cami
Free People

A lace cami that isn’t skin-tight…

If you like clothes that feel like you’re wearing next to nothing, you’ll love this flowy, lace-trimmed camisole from Free People’s in-house brand Intimately. The collection includes lightweight, romantic loungewear and intimates that are cute enough to wear out, but comfortable enough to sleep in. Throw this over a long-sleeve tee for a ‘90s-inspired look, or a bralette to keep the boho vibes going. ($38

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We The Free Most Loved Long Sleeve
Free People

A long-sleeve tee worth adding to your capsule collection…

You may already have a closet full of long-sleeve tops, but the boat neckline on this one is undoubtedly chicer than the rest. It's still a great layering piece, thanks to the fitted silhouette. Throw it on over a sports bra and leggings to a workout class, or under a sweater on colder days. ($38)  

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