Kendall Jenner
It's easy to wear the polka dots in the summer. Just throw on your statement piece (in Kendall's case, it's this strapless mini) and go, right? Keep things casual with simple white sneakers and cat-eye shades to protect against those UV rays. Add a bold accessory for a pop of color and intensity.
For Summer
Lisa Marie Fernanez Imaan Tiered Polka-Dot Cotton-Voile Mini Dress, $745; Kendall + Kylie Charli 52mm Cat Eye Sunglasses, $145; Urban Outfitters Charlotte Phone Crossbody Bag, Was $29; Now $19.99; Kenneth Cole New York Kam Sneaker, Was $11.95; Now $84.99-$95.99
Olivia Culpo
When it's not quite sweater weather, but the temps have dropped a smidgen, follow in Olivia's footsteps. The former beauty queen has mastered transitional styling, pairing a Pretty Little Thing mini over a Jean Atelier oversize button-up for a covered-but-sexy look. Her long white boots will keep her legs warm and toasty. To replicate this look, throw a dress with a low neckline over your tried-and-true white blouse. Just don't forget your fall boots. Our favorite right now? Stuart Weitzman SW x You Made-to-Order Boots. You can custom create your own steppers from the brand's eight silhouettes and 14 colors and materials. Shop these limited-edition kicks before September 10.
For Transitional Weather
H&M Short Cotton Dress, Was $24.99, Now $12.99; Uniqlo Women Supima Cotton Stretch Long Sleeve Shirt, $29.90; DKNY Nappa Leather Mini Backpack, $225; Stuart Weitzman The Flatscrunchy Boot, $775
Gwen Stefani
Fall layering can be difficult. Take style notes from Gwen, whose flowy Zimmermann frock just inspired our next fall-appropriate, polka-dot ensemble. The singer's dress is almost sheer—because of the light fabric, the different sizes of polka dots and lace look almost like they are layered together. That, combined with the high-low hem of the dress, mixed with the over-the-knee boot, makes for a chic-yet-edgy autumn look. When the weather gets colder, add cropped trousers under your sheer dress and a denim oversize jacket on top.
For Fall
Zara Irregular Polka Dot Top, $69.90; Topshop Oversize Denim Jacket, $90; J.Crew PetiteCameron slim crop pant, $79.50; Sarto by Franco Sarto Palmer II Genuine Rabbit Fur Slide, $108.95