4 Cool Denim Outfit Combinations We're Adding to Our Fall Wardrobes

If you were to ask me and my coworker Angelica Zdzienicki which clothing item we could never live without, the answer would be easy: anything denim. Regardless of the season, we never hesitate to reach for denim when opening our closets, and while trends come and go, we know we can always rely on it for longevity and versatility. As the fall season approaches, we’re coming up with cool denim outfit combinations we can wear for all our autumn activities, and Free People’s in-house brand We the Free was the first place that came to mind when we began our shopping quest.

When it comes to fall wardrobe staples, Angelica and I both like it when classic pieces have unexpected and unique details that set them apart. We the Free has just that—after viewing the brand’s abundant selection, we gravitated towards the flared and barrel-leg jeans for their on-trend silhouettes. The wide range of boots—from Western pointed-toe styles to edgy, cropped moto boots—is pretty impressive too. And of course, we were able to find perfect basic pieces like long-sleeve tees and cute cardigans to complete our looks. Expect to see us in these four denim outfits this fall.

“I am a baggy-denim enthusiast and have been wanting to hop on the barrel jeans trend for a while now, so when I saw We the Free’s Good Luck Mid-Rise Barrel Jeans in the Falcon Grey colorway, I knew it was my time to shine. These are the perfect statement pants, plus the fit is so flattering. I paired them with a simple long-sleeve tee, the Janey Engineer Boots, and the Emerson Tote to give the ‘fit a chic-meets-edgy vibe. My go-to cool-girl uniform is now complete for the new season.” — Angelica Zdzienicki, social media strategist

While you might think the obvious choice for a denim outfit is a classic pair of jeans, I chose a denim jacket instead. It’s the perfect layering piece for the summer-to-fall transition, and the dropped shoulders give it an effortless shape. I styled it with cream corduroy barrel pants to create a cool, neutral moment. (By the way, I’m recommending these pants to everyone I know for their insanely comfortable fit.) For finishing touches, I accessorized with leather pointed-toe boots and a slouchy bag to add some texture. This outfit is ideal for both daytime hangouts with my friends and all the concerts I plan on going to this fall.

“I get endless compliments whenever I wear these Dropped Boyfriend Jeans. They’re not only stylish but also incredibly comfortable. To keep it simple, I paired them with a matching cozy cardigan and black studded belt, so the red shoes could really stand out. Whether I’m apple picking or grabbing dinner, this is the timeless look you’ll catch me in.” — Zdzienicki

If you ask Angelica, she’ll agree that it’s rare to find me in anything other than flared-leg jeans. That’s why We the Free’s Level Up Slit Slim Flare Jeans instantly grabbed my attention. I kept the styling minimal and opted for the cute, ultra-soft Pointelle Baby Tee and square-toe ankle boots. Luckily, the fall season in Los Angeles is never too chilly, so as long as my feet are warm, I know I’m good to go. But when the temperature does start to drop, this outfit will make for a great foundational look, since it can be layered with a sweater or oversize jacket.