30 Doable Ways to Upgrade Your Style This Fall

Welcome to our 11th 30-day wardrobe challenge! By now you should know the drill but if you’re new, here’s how it works. We set four weeks’ worth of outfit and style tips for you to test out over the next 30 days, in hopes to update and reboot your style for the new season. To keep things interesting, this round we changed it up a bit and reached out to some of our power challenge participants from previous seasons and had them submit and select a selection of the challenges. So the first 19 challenges you see below were created by a handful of our most engaged 30-day users. Are you ready to check out the latest fall style challenges?

Scroll down to see all of the challenges, and be sure to share your looks with the hashtag #WWWfall30 for a chance to be featured on our site at the end of the month.

Day 5: Combine several textured fabrics.

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@cuddlepill

Day 8: Take your LBD to the next level with chic metallic shoes.

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@messybunsandburgers

Day 10: Try a menswear-inspired look.

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@shantelrousseau

Day 11: Make your slip dress appropriate for fall by layering.

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@madeby8

Day 14: Pair a silk kimono with bright colors.

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@shewearscolor

Day 15: Transition your summer skirts into fall with over-the-knee boots.

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@stephweizman

Day 20: Add a pop of red to your denim on denim.

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Collage Vintage

Day 21: Tuck in your fall sweaters for a sleek look.

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Collage Vintage

Day 22: Pair your favorite slip with an oversize blazer.

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Collage Vintage 

Day 23: Test out the polka-dot trend.

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Collage Vintage 

Day 24: Swap your go-to hat for a chic beret.

Collage Vintage

Day 25: Wear all black with sleek white ankle boots.

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Collage Vintage

Day 26: Style a statement top with loose-fit jeans.

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Collage Vintage

Day 27: Buy a pair of red boots.

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Collage Vintage

Day 28: Dress up your sweaters with classic heels.

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Collage Vintage

Day 29: Style your leather pants with a cozy fall sweater.

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Collage Vintage

Day 30: Wear bright boots with a two-piece suit.

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Collage Vintage

Up next, shop fall's most popular boot silhouette

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