Outfit Ideas: 6 Cute Ways to Wear Your Summer Sundress Straight Into Fall

Don’t pack away last season’s go-tos just yet.

Strapless Floral Under a Sweet Sweatshirt

This summer staple looks fresh with a très chic sweater and a turquoise carryall. Pair with poppy suede flats to keep your toes warm.

Thread Social strapless dress, $174 at the Outnet; Zoe Karssen Ooh La La sweater, $160 at Net-a-Porter; suede ballet flats, $38 at Asos; patent-leather carryall pouch, $56 at American Apparel; brass cuff, $100 at Pyramid Collection; Swatch watch, $50 at Macy’s; and earrings, $11 at Go Jane.

Relaxed Maxi

The black maxi dress is a staple for all seasons—keep it cool-weather-appropriate with a trench, flats, and a fun clutch.

Kate Spade clutch, $78 at Nordstrom; maxi dress, $51 at Romwe; drawstring trench coat, $64 at She Inside; Steve Madden flats, $90 at Piperlime; Vince Camuto collar necklace, $58 at Macy’s; chain bracelet, $98 at Juicy Couture; and Marc by Marc Jacobs stud earrings, $62 at My Wardrobe.

Stripes and Mules

Pair a nautical-inspired dress with an olive parka or a military jacket, then add some eye-catching metallic mules and tough-girl jewelry for a look that’s equal parts preppy and edgy.

J.Crew striped dress, $188 at Net-a-Porter; Elizabeth and James parka, $295 at Otte; Reed Krakoff mules, $263 at the Outnet; Parker satchel, $68 at Nasty Gal; spike necklace, $24.99 at Modcloth.

Pink on Pink

Taking your summer shift to fall is the perfect opportunity to color-block—top a dress with a sweater in a matching tone for a cool cool-weather outfit. Make it playful it with a contrasting necklace and some unexpected snakeskin boots.

Acne zip-back knit sweater, $300 at My Wardrobe; Vince shift dress, $239 at Barneys; Chelsea Crew snakeskin bootie, $90 at DSW; Rebecca Minkoff cross-body bag, $295 at Stefani Bags; Blu Bijoux beaded necklace, $29 at Max & Chloe.

Country Casual

That chambray dress you bought back in May was made to be worn with a comfy, oversize cardigan and some walkable boots. This look is perfect for fall sightseeing on the Mall—stash your cash in a chic orange credit card holder and use a classic camera bag as a purse.

Denim dress, $35 at Mango; Girl by Band of Outsiders cardigan, $335 at Barney’s; control-top tights, $27 at J.Crew; McQ ankle boots, $625 at the Corner; Blu Bijoux earrings, $26 at Max & Chloe; Vans camera bag, $32 at Swell; credit card holder, $165 at Prada.

Rainy-Day Chic

Drizzling outside? Toughen up your weekend T-shirt dress with some wedge sneakers, then top with a bright jacket, a cashmere scarf, and a textured bag.

John Patrick oversize T-shirt dress, $88 at La Garçonne; anorak, $62 at She Inside; wedge sneakers, $90 at Topshop; clutch, $70 at Topshop; Skagen watch, $95 at Nordstrom; Loren Stewart earrings, $85 at Barney’s.