12 Ways to Wear Summer Dresses for Fall

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How many of us splurged on a breezy little dress in May, but feel it's not seasonally appropriate once September rolls around? Guilty! But here’s the thing: Just because the temperatures begin to drop as we head into fall doesn't mean we're willing to call it quits on our summer wardrobes so soon. You can still wear your summer dresses in the fall, it will just take some extra styling effort.

A great way to get more mileage out of your summer dresses before you pack them up for the colder seasons ahead is to layer, layer, layer. From white button-downs to tees, there are plenty of ways to give your favorite wispy frocks a second life, like transforming a fun spaghetti-strapped number with a turtleneck underneath. The trick is to evaluate the pieces in both seasonal wardrobes to see what works with your fall outfits. That said, if you’re standing in front of a pile of clothes and the inspiration just isn’t sparking, don’t panic.

Ahead, we’ve rounded up 12 ways to wear your summer dresses during fall that won’t require a shopping trip — just an assessment of your closet.

Break Out a Plain White Tee

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It can’t get any easier than this early aughts styling technique. Layer a simple white T-shirt with a V-neck dress for added coverage, and add a camel overcoat for extra warmth.

Go for a Tonal Approach

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Quiet Luxury will continue to be everywhere this upcoming season. An easy way to emulate it is to focus on rich, tonal hues. A minimal oxford under a dress in a similar hue provides a seamless look; add embellished heels for a bit of a statement.

Related: The Fall 2023 Colors Everyone Will Be Wearing

Add Unexpected Pieces

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Give onlookers something to talk about with unusual pieces layered together. For instance, distressed jeans are a fall-ready pairing to a lightweight dress, and look extra unexpected with sneakers.

Pump Up the Volume

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Play up your dress's full skirt by pairing it with an equally voluminous top. To channel your inner street-style star, just add sneakers or chunky boots.

Lightly Layer Up

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It probably comes as no surprise, but one of the easiest ways to transition your summer dresses for fall is by throwing on a sweater or jacket. However, because the segue from summer to fall isn’t blazing hot or frigid, personal style advisor at MiKADO Personal Styling Jordan Stolch says lightweight outer layers are key — think unstructured boyfriend blazers and breezy cardigans.

Add Contrast with Leather

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Summer dresses tend to be light and airy. Fall has a different aesthetic; it’s cozy and the outfits tend to have more moving parts (not literally, but you get it). Ergo, to transition your summer dresses into fall, celebrity stylist Tyler Minor suggests adding a tougher exterior layer, like a leather trench coat, to a daintier foundation layer, like a slip dress. “The juxtaposition of a leather trench and a satin slip dress works beautifully together,” Minor says.

Elevate Your Look with a Blazer

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Never will we ever not ship a blazer in the fall, especially when paired with a summer dress. Fashion stylist and style expert Naina Singla concurs, adding that not only are they sophisticated, but a '90s-style double-breasted blazer with broad shoulders and a boxy silhouette can elevate basics like a neutral cotton tank maxi. “Hang it over your shoulders with tall black boots for a chic and polished look that transitions from day to night," says the stylist.

Cozy Up Your Summer Shades

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Stitch Fix stylist Courtney Busch pleads that you don’t put vibrant-hued pieces away come fall. Instead, you can add contrasting colors and cozy accessories. Busch says one of her favorite ways to transition a pink summer dress for fall is “by styling it with a pair of knee-high boots.”

Pair It With a Tall Boot

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Fall is boot season, so when Madeline Cronin Aaronson, the brand director of thredUP, says her favorite way to wear summer dresses in the fall is to pair them with her favorite boot, we can think of no better footwear pairing. “I’m obsessed with Alison Bornstein’s 'wrong shoe theory' and think it applies so well here,” Cronin Aaronson tells InStyle. “Adding an unexpected neutral cowboy boot or black riding boots is such a good look. It also covers more skin when temps start dropping.” Stylist Kathryn Hamed concurs, adding a leather or suede boot “instantly winterizes the look without looking seasonally displaced.”

Related: You Can Wear These 11 Fall Shoe Trends Right Now

Belt It

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Statement belts are coming back, so if you loved the look when it was hot in the early aughts, you’ll love Cronin Aaronson’s second tip: To transition your summer dress to fall status by incorporating belts into your wardrobe. “Add a belt at the waist, particularly a belt with textured leather or heavier hardware that adds some cool weather gravitas to your ‘fit.”

Toy with Tops

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Stylist and style therapist Christina Stein is all about marrying your favorite tops with your favorite summer dresses to create a fall-appropriate fit. “That white button-up that you've been wearing with your favorite linen trousers this summer can have a new life with a sleeveless leather dress and a fabulous pair of red pumps,” Stein says. And that sheer top you've been wearing on repeat this summer? “Easily pair it with cotton dresses and sleek sneakers. or pair that classic dress with a power blazer and over-the-knee boots.”

Stick to Close-Toed Shoes

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Time to turn in your flip-flops, friends. Designer Angela Horton, founder of AngelaHorton.com, agrees it’s all about shoes when it comes to wearing summer dresses in fall. “In the summer you want to wear fun open-toed shoes and heels with your dresses, but as we transition to fall, you can swap out your summer shoes for closed-toed pairs, like calfskin ballerina flats or sophisticated suede pumps,” Horton tells InStyle. “This not only keeps your feet warmer as the weather cools but also signals that your favorite dress is in fall mode.”

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