7 Comfy and Stylish Looks That Will Have You Feeling Like a Street Style Star All Week

Sweater-and-jeans fatigue is a real thing! You can be so much more expressive when you mix things up, which is why we’re challenging you to make this season your most fashionable Fall yet by embracing trends, wearing new colors, and stepping out of your style comfort zone. To help get you started, we’re encouraging you to embody a new trend for seven days in a row. Starting with leopard print and ending the week with corduroy, you’ll find yourself thinking outside the box and, in turn, stopping any future outfit ruts dead in their tracks.

Find inspiration below from seven chic outfits that are not only fashion-forward, but also comfortable — i.e. not a pair of heels in sight. Because when it comes down to it, confidence and comfort go hand in hand, and when you feel good, you look good. These looks will help you fearlessly conquer whatever the season may throw at you, from parties to dinners to outdoor adventures. Get ready to look at Fall fashion from a fresh, new lens!

DAY 1: LIVING FOR LEOPARD

Start the week off strong by having leopard print — or any animal print of your choosing — punctuate your OOTD. Just how wild you want to go is totally up to you! Ease into the trend with a leopard bag or headband, or go all out head-to-toe. Either way, think of animal print as your new go-to neutral and mix and match it with bold jewel tones and different textures. You truly can’t go wrong, as this print even vibes with polka dots or stripes. Tan suede boots complement the print even further and really make it pop.

DAY 2: CHECKMATE

Day two is all about relaxed sophistication. Championing plaid and its effortless versatility, try the pattern on for size in the form of an oversized blazer, ankle pants, or even a scarf. With the ability to add instant polish to any ensemble, plaid is definitely a print you want to have in your fashion arsenal. Here, we layered the pattern over a simple jeans-and-tee combo for an easygoing vibe that’s still elevated. We finished it off with sensible yet stylish booties in a surprisingly versatile rich burgundy.

DAY 3: MAKING VARSITY

On day three, we’re challenging you to get a little sporty. Incorporate athleisure into your look by wearing track pants, varsity sweaters, or athletic bomber jackets. To put a Fall spin on the trend, reach for an elevated version of your go-to sneakers — like these leather high-tops that are a unique boot-sneaker hybrid. This casual cool-girl trend isn’t going anywhere, so there’s no better time to start experimenting with it.

DAY 4: GO FUR IT

OK. Bear with us here. Fur may seem like an intimidating trend to try, but trust us, you can make it work. And after all, this wouldn’t be a style challenge if we didn’t make you get at least a little uncomfortable. For starters, the best way to style such a dramatic piece is by choosing low-key shoes — like these ready-for-anything boots. A pair like this is not only practical and comfy, but it helps bring louder pieces back down to earth. Sticking with a simple color palette is also key and will instantly help ground faux fur.

DAY 5: MELLOW YELLOW

Yellow is the new It color! For Fall, the hue has been showing up everywhere in toned-down shades of mustard, gold, and canary, and your challenge for day five is to integrate some form of the color into your look. Aside from providing a fun burst of optimism in color form, yellow is surprisingly versatile and adds instant charm to any outfit. For a whimsical feel, pair it with a bold print or a jewel tone. Plaid, on the other hand, looks extra smart next to the hue, as does a durable pair of brown booties.

DAY 6: HEADING WEST

Western-inspired pieces are having a major moment. Saddle up to the trend in a colorful pair of boots that boasts an American heritage look and feel. With a wool Pendleton motif, these boots will distinguish you from the pack, giving your outfit a unique edge. Denim-on-denim also fits right in here as does fringe and anything suede. In an effort to look more fashion than cowboy, opt for a wide-brim fedora hat and delicate gold jewelry.

DAY 7: CORDUROY COMFORT

The last day of our challenge is your opportunity to dive head first into a sea of luxurious comfort. After all, lush fabrics like velvet and corduroy were made for Fall, and not only are these textures beautiful and soft, they’re also extremely polished and comfortable. There are so many corduroy pieces to choose from this season, but we’re partial to dresses layered over a long-sleeved turtleneck. Team these rich fabrics with footwear that’s just as refined — like these premium gray leather booties. And, let’s be real, who doesn’t love a pair you can easily slip on and off?

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