14 Chic Dress and Sneaker Pairings to Travel in This Fall

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sneaker and dress outfit
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In fashion, comfort and style don't always go hand in hand. In fact, when it comes to looking trendy, feeling comfortable is far less likely to be a factor — we're looking at you high heels, skinny jeans, and crop tops. Fortunately, the fashion world is slowly but surely warming up to the idea that we are not all supermodels walking up and down a runway all day long, so designers have finally turned towards a more comfort-inspired aesthetic that focuses on well-being, simplicity, and effortlessness.

Thanks to this shift in creative direction, a combination that would have raised quite a many eyebrows a few years ago is now at the forefront of street style — we're talking about the unlikely marriage of dresses and sneakers. The trend started slowly, making its way into the suitcases of influencers and It-girls headed for a grueling month of shows during fashion month as a more comfortable alternative to the classic stilettos/dress combo. Now, it's been fully adopted by everyone from High Street to high-end.

Related:16 Comfortable Dresses That Are Made to Travel In

Of course, while we fully endorse this cool, travel-friendly trend, there are a few rules to follow that guarantee a successful sneaker-dress ensemble. First of all, a pair of plain white sneakers is a must-have; you can pair them with virtually anything for a cool look. Another way to go about finding the perfect pair of kicks to wear with your favorite floral dress is to pick one color from your dress's print and opt for solid sneakers in that shade.

If you own a statement pair of sneakers with unique accents such as shearling, fur, metal detailing, or an unusual silhouette, choose a dress that's more on the classic side so that all the attention is on your shoes. And note: feminine styles like slip dresses pair well with kicks in soft pastel shades.

Now, check out 13 cool and stylish dress and sneakers combinations to update your closet with this season.

01 of 13

Mango Floral Vintage Dress & Valentino 'Bounce' Low-top Leather Trainers

dress and sneakers outfit
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Bold '70s prints are having a fashion moment and this flowy Mango dress is the perfect way to be a part of it. It has a vintage shirt collar and an elastic waist with an adjustable drawstring for a custom fit. We love the juxtaposition of the dress's vibrant print and the simplicity of this pair of white Valentino trainers with chunky rubber soles.

To buy: (dress) mango.com, $80; (sneakers) matchesfashion.com, $845

02 of 13

Everlane The Japanese GoWeave Light V-neck Dress & Michael Michael Kors 'Allie' Leather Trainer Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

A dress and sneaker combo doesn't necessarily need to be sporty. This beautiful olive green V-neck dress from Everlane is so effortlessly chic — and wrinkle-resistant. To match its vibe, we love these Michael Kors' leather embossed sneakers that feature metal accents.

To buy: (dress) everlane.com, $79-$94; (sneakers) zappos.com, $135

03 of 13

Gant Preppy Striped Shirt Dress & Saucony Originals 'Jazz Original' Sneakers

dress and sneakers outfit
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Play the color block game by pairing this preppy, weekend-ready shirt dress with these bright Saucony kicks. You can opt to wear the dress off-the-shoulder or as a crew neck.

To buy: (dress) gant.com, $92 (originally $185); (sneakers) zappos.com, $60

04 of 13

French Connection 'Aventine Plains' Midi Shirt Dress & Acne Studios 'Manhattan' Leather Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

Whether you like it or not, "dad sneakers" are here to stay, and we have to admit that they definitely deliver in the comfort department. That's why we wouldn't mind styling a pair with this simple, relaxed shirt dress by French Connection. It's an outfit we could literally live in.

To buy: (dress) frenchconnection.com, $128; (sneakers) mytheresa.com, $470

05 of 13

Foxiedox 'Retro Flowers' Midi Dress & Ugg 'Tye' Sneaker

dress and sneakers outfit
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Ugg's super-comfy leather sneakers will pair well with almost anything, but we love how they make this busy-in-the-good-way midi into a more casual look.

To buy: (dress) nordstrom.com, $170; (sneakers) nordstrom.com, $140

06 of 13

Ace&Jig 'Annalise' Striped Cotton Wrap-dress & Gucci Embroidered Leather Sneakers

dress and sneakers outfit
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Run errands while looking stylish and feeling comfortable in this green-and-beige-striped cotton wrap dress by Brooklyn-based label Ace&Jig and Gucci's leather sneakers, which are now a millennial-favorite.

To buy: (dress) matchesfashion.com, $356; (sneakers) net-a-porter.com, $620

07 of 13

Michael Michael Kors Belted Midi Dress & Adidas 'Superstar' Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

If you're not a fan of the "no white after Labor day" rule, then this combination is perfect for you. Michael Kors' breezy pleated midi dress and a pair of classic Adidas Superstar sneakers are a match made in monochromatic heaven.

To buy: (dress) net-a-porter.com, $175; (sneakers) nordstrom.com, from $80

08 of 13

Gap Floral-print Long-sleeve Midi Dress & Eric Michael 'Zoya' Espadrille Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

Gap's black floral maxi dress is a fall must-have. Style it with a leather jacket and Eric Michael's Zoya espadrille-inspired sneakers in blue-gray suede for the perfect boho look.

To buy: (dress) gap.com, $90; (sneakers) zappos.com, $85

09 of 13

Lisa Marie Fernandez Floral-print Maxi Dress & Superga '2750 Satinjaquardw' Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

For those Indian summer days this fall, opt for a lightweight dress like this retro-inspired Lisa Marie Fernandez number in breathable cotton-voile and Superga's floral sneakers in satin.

To buy: (dress) net-a-porter.com, $745; (sneakers) zappos.com, $99

10 of 13

Tibi Open-back Sweatshirt Midi Dress & Adidas by Stella McCartney 'Ultraboost X' Low-top Trainers

dress and sneakers outfit
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This dress undeniably falls into the althleisure category, but there's also something really chic about it — maybe it's the slightly puffy sleeves or the open back that reveals just the right amount of skin. One thing is certain; it deserves a similarly smart pair of sneakers to wear it with. The Ultraboost X cuts a sporty silhouette but the leopard-print soles add a touch of off-the-court elegance.

To buy: (dress) tibi.com, $475; (sneakers) matchesfashion.com, $231

11 of 13

Veronica Beard 'Adora' Dress With Free People Thermal Tee & Josef Seibel 'Sina 11' Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

This is the perfect outfit to brighten up a dark and cloudy autumnal day. Veronica Beard's "Adora" dress is the versatile midi every women needs in her closet. The contrast stitching contributes to its slightly casual vibe and denim-like appearance. In the fall we'd wear it over this bright Free People long-sleeve tee with leather sneakers in a similar saffron hue.

To buy: (dress) veronicabeard.com, $595; (shirt) nordstrom.com, $41; (sneakers) zappos.com, $122

12 of 13

H&M Dress With Tie Sleeves & Tretorn 'Marley' Canvas Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

This cool LBD and sneakers combo is courtesy of Swedish brands H&M and Tretorn. The dress hits at mid-thigh and features cute bow ties at the sleeves. Freshen up the look with these low-top canvas kicks in a floral pattern created in collaboration with British print house Liberty London.

To buy: (dress) hm.com, $20; (sneakers) jcrew.com, $75

13 of 13

Topshop Pinafore Midi Dress With Madewell 'Whisper White' T-shirt & New Balance 'Fresh Foam Zante v4' Sneakers

dress and sneakers outfit
Courtesy of Respective Retailers

Topshop's bright midi features a draped skirt and a deep V-neck that may be too much for some. Just wear it over a white T-shirt if that's the case — it'll also make the look a bit more casual. Finally, this pair of hot pink New Balance sneakers that matches the flowers in the dress's print, will tie the whole look together.

To buy: (dress) topshop.com, $100; (shirt) nordstrom.com, $20; (sneakers) zappos.com, $90 (was $100)

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