Call me stubborn or hardheaded or whatever but I refuse to allow the weather to dictate my closet. I mean clearly, I'm leaning into all the fall trends (have you seen these dresses?) But as it gets chillier, I won't be transitioning out of my summer closet entirely. And you should consider doing the same! Instead of storing away all those dresses, you should pull out the cardigans, knee-high boots, and jackets instead. To make styling simpler (but obvi so fun), here's a shoppable street style roundup with tons of inspiration for you. Trust me, these looks are worth braving any lil chill for!!!
A Cropped Jacket
Cropped jackets are always a move, especially when they're structured (makes them look so chic). If you'd like to wear this in a more profesh setting, go for a blazer dress or a windowpane design underneath.
Shop the Cropped Jacket Look
Plaid to Be Yours Beige and Brown Plaid Pinafore Mini Dress
Ava & Viv Women's Tailored Mini A-Line Dress
H&M Bouclé Jacket
A Zipped Hoodie
Chill out in a zipped hoodie and matching dress. If you're feeling too casual, a bright bag will give your 'fit the pop it needs.
Shop the Zip-Hoodie Look
Aritzia Cozy Fleece Mega Drop Shoulder Zip Hoodie
lululemon Align™ Dress
JW Pei Abacus Faux Fur Mini Top Handle Bag - Orange
A Suede Jacket
Suede material automatically makes everything look schmancy—especially if it's in a trench form! Go with a brown ruched number and sunnies for a boss slay.
Shop the Suede Trench Look
Anthropologie Faux-Suede Trench Coat
Murci Honeycomb Knit Cut Out Halterneck Maxi Dress
A Denim Trench
Sure, you can wear a typical denim jacket, but, just so you know, you can also level up with a denim longline jacket. Add some cool sunnies and some mules and voilà, you're that girl.
Shop the Denim Trench Look
BAUM UND PFERDGARTEN Delilah Trench Coat
RAYE Polina Heel in Ivory
A Fur Jacket
You'll feel fabulous in a fur jacket and a tiered dress. Look at this picture and tell me I'm wrong.
Shop the Faux Fur Look
ELOQUII Bridal by ELOQUII Faux Fur Jacket
A Varsity Jacket
It's game time: Go for an unexpected combo like a varsity jacket and a tulle dress! Take it a step further with exaggerated boots like this pair from Moon Boot.
Shop the Varsity Jacket Look
Petal & Pup Belle Swiss Dot Tulle Tiered Maxi Dress
Moon Boot Icon Nylon Boot
An Oversized Blazer
No way could we do this roundup without an oversized blazer look. I'm sure you've worn yours with your fave jeans a million times, but how about reaching for a knit midi dress instead to switch it up?
Shop the Blazer Jacket Look
Abercrombie Slash Knit Midi Dress
Sam Edelman Kasey Square Toe Ballet Flat
A Utility Jacket
Utility jackets are cool, but you wanna know what's cooler? One that's composed of vinyl material. A mesh dress is always a sultry vibe and pairing it with this type of jacket will be edgy and practical in the best way.
Shop the Utility Jacket Look
H&M Coated Utility Jacket
A Bomber Jacket
School everyone who thinks they know how to style a bomber jacket by elevating yours with a shearling collar, striped dress, and loafers.
Shop the Bomber Jacket Look
BLANKNYC Bomber Jacket in Black
Stuart Weitzman Parker Lift Loafer
A Leather Jacket
Ofc, you can wear a leather jacket—a long leather one fits a more mature (and Matrix-y) aesthetic and adding a midi denim dress keeps things casual, but elevated.
Shop the Leather Jacket Look
Reformation Kendi Denim Midi Dress
Good American Chino Faux Leather Trench Coat
Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle about 10 years ago. Since then, she's also served as the style editor at The Haitian Times. The Haitian-American pageant queen is Miss Supranational Haiti 2024, a Syracuse Masters graduate, and the author of three books, including: Claim Your Crown. Follow her on Instagram and TikTok: @iamtarahlynn.
