30 Doable Ways to Upgrade Your Style This Fall

last updated 13 August 2019

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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.

fall-style-challenge-237265-1506631301515-image — Day 1: Pair a turtleneck with statement trousers.

fall-style-challenge-237265-1506631305137-image — Day 2: Sport the patterned suit trend.

fall-style-challenge-237265-1506631303803-image — Day 3: Go for an easy three-piece ensemble for fall.

fall-style-challenge-237265-1506631306006-image — Day 4: Try a statement sleeve.

fall-style-challenge-237265-1506631297671-image — Day 5: Combine several textured fabrics.

fall-style-challenge-237265-1506631299572-image — Day 6: Wear a statement sweater.

fall-style-challenge-237265-1506631300709-image — Day 7: Play around with different fall prints.

fall-style-challenge-237265-1506631302462-image — Day 8: Take your LBD to the next level with chic metallic shoes.

fall-style-challenge-237265-1506631304377-image — Day 9: Mix unexpected prints for a bold office look.

fall-style-challenge-237265-1506631302735-image — Day 10: Try a menswear-inspired look.

fall-style-challenge-237265-1506631301820-image — Day 11: Make your slip dress appropriate for fall by layering.

fall-style-challenge-237265-1506631301256-image — Day 12: Wear plaid in an unexpected way.

fall-style-challenge-237265-1506631303043-image — Day 13: Embrace a French-inspired outfit.

fall-style-challenge-237265-1506631303359-image — Day 14: Pair a silk kimono with bright colors.

fall-style-challenge-237265-1506704515941-image — Day 15: Transition your summer skirts into fall with over-the-knee boots.

fall-style-challenge-237265-1506631304079-image — Day 16: Update your outerwear with an oversize trench coat.

fall-style-challenge-237265-1506631304641-image — Day 17: Pair socks with sandals or heels to add edge to your outfit.

fall-style-challenge-237265-1506631305420-image — Day 18: Step up your sneaker game by tying your laces around your ankles.

fall-style-challenge-237265-1506631305741-image — Day 19: Try pairing an oversize blazer with neutral colors.

fall-style-challenge-237265-1506631306360-image — Day 20: Add a pop of red to your denim on denim.

fall-style-challenge-237265-1506631306593-image — Day 21: Tuck in your fall sweaters for a sleek look.

fall-style-challenge-237265-1506631306959-image — Day 22: Pair your favorite slip with an oversize blazer.

fall-style-challenge-237265-1506631307195-image — Day 23: Test out the polka-dot trend.

fall-style-challenge-237265-1506705407101-image — Day 24: Swap your go-to hat for a chic beret.

Collage Vintage

fall-style-challenge-237265-1506631307442-image — Day 25: Wear all black with sleek white ankle boots.

fall-style-challenge-237265-1506631308205-image — Day 26: Style a statement top with loose-fit jeans.

fall-style-challenge-237265-1506705408696-image — Day 27: Buy a pair of red boots.

fall-style-challenge-237265-1506631308594-image — Day 28: Dress up your sweaters with classic heels.

fall-style-challenge-237265-1506705409345-image — Day 29: Style your leather pants with a cozy fall sweater.

fall-style-challenge-237265-1506631307767-image — Day 30: Wear bright boots with a two-piece suit.

Up next, shop fall's most popular boot silhouette.

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