As the days grow shorter and the air gets cooler, it can be tough to let go of those breezy summer dresses. But don’t worry! You don’t have to pack them away just yet.
With the right layering and accessories, summer dresses can effortlessly transition into the fall season. Whether it’s with a stylish jacket, tights, or boots, here are 20 dresses that can take you from the sunniest days of summer to the crisp afternoons of autumn.
Sleeveless A-Line Dress with a Cardigan
A sleeveless A-line dress is the perfect base for layering. Throw on a cozy cardigan or a denim jacket, and you’ve instantly created a look suitable for cooler temperatures.
Pair with tights and ankle boots to complete the look, and you’re good to go!
Maxi Dress with a Leather Jacket
Maxi dresses are great for summer, but they can easily carry over into fall with a bold leather jacket. The juxtaposition of a flowing, feminine dress and a tough leather jacket creates an effortlessly stylish vibe.
Add some boots, and you’ve got a chic outfit perfect for fall.
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Button-Down Shirt Dress with a Wool Coat
Button-down shirt dresses are a year-round staple, and they transition beautifully into cooler weather. Layer it with a structured wool coat and a pair of knee-high boots for an elevated look.
The structure of the coat contrasts perfectly with the relaxed style of the dress.
Wrap Dress with a Turtleneck Underneath
Wrap dresses are timeless, flattering, and adaptable. For a fall-ready outfit, layer a thin turtleneck under your wrap dress. This adds warmth without sacrificing style and allows you to still showcase the dress’s silhouette.
Pair with tights and a scarf for extra coziness.
Floral Dress with a Moto Jacket
A floral dress screams summer, but paired with a moto jacket, it’s perfect for the chillier months. The bold, edgy jacket balances the softness of the floral print, making it ideal for transitioning.
Add a pair of combat boots for a more daring look.
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Shirt Dress with Over-the-Knee Boots
A classic shirt dress gets a fall makeover when paired with over-the-knee boots. The boots add warmth and a stylish edge, while the shirt dress remains light enough for transitional weather.
Layer with a scarf or vest for added dimension.
Slip Dress with a Chunky Knit Sweater
Slip dresses are chic and versatile, and they can take on a cozy, fall-ready vibe when layered with a chunky knit sweater. Let the sweater drape over the dress, and pair with tights or leggings for comfort and warmth.
Add some booties, and you’re set for autumn.
T-Shirt Dress with a Plaid Blazer
A simple T-shirt dress becomes a polished fall outfit when you add a plaid blazer. The blazer brings structure and warmth, while the relaxed T-shirt dress keeps the overall look casual yet stylish.
Finish with a pair of slip-on sneakers or boots.
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Sundress with a Knitted Vest
Your favorite sundress doesn’t have to stay packed away for the fall. Layer it with a knitted vest to add texture and warmth.
The vest adds a touch of fall flair, while the sundress retains its summery feel. Pair with boots or sandals for a laid-back look.
Midi Dress with a Trench Coat
A midi dress is the perfect option for layering as the weather cools. A classic trench coat works wonders over a midi dress, giving the outfit a timeless, sophisticated feel.
Add tights and loafers for a chic, comfortable look for both work and weekend outings.
Off-the-Shoulder Dress with a Cozy Scarf
Off-the-shoulder dresses can be worn into the cooler months by adding a large, cozy scarf. The scarf will keep you warm while allowing the dress to shine.
Pair with boots and tights for a more practical look while still showing off the playful off-the-shoulder neckline.
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Tank Dress with a Lightweight Denim Jacket
A simple tank dress is a versatile piece that works well into fall when paired with a denim jacket. The lightweight jacket adds just the right amount of warmth while still letting the dress take center stage.
Complete the look with ankle boots and layered jewelry.
Smock Dress with a Sweater Vest
Smock dresses are perfect for layering. To transition it into fall, add a sweater vest over the top for extra warmth.
The loose fit of the smock dress contrasts with the cozy texture of the sweater vest, creating a stylish balance.
Shift Dress with a Longline Cardigan
Shift dresses are the epitome of simplicity and elegance. When paired with a longline cardigan, they are the perfect balance of warmth and style for cooler days.
Add tights and a scarf for extra coziness, and swap sandals for boots to complete the look.
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Peasant Dress with a Fitted Blazer
Peasant dresses, with their billowy sleeves and flowing fabric, can be styled for fall by adding a fitted blazer. The sharpness of the blazer contrasts with the softness of the dress, giving it a chic, put-together appearance.
Finish with ankle boots and a wide-brim hat.
Cami Dress with a Long-Sleeve Top Underneath
Cami dresses are lightweight and perfect for layering. Wear a fitted long-sleeve top underneath to give it a fall-friendly twist.
This adds extra warmth while still allowing the dress to shine. Pair with tights or leggings and boots to keep cozy as the temperature drops.
Shift Dress with Over-the-Knee Boots
Shift dresses are a great option for layering. Pairing one with over-the-knee boots creates a sleek, fashionable look.
The boots add warmth and style, while the shift dress remains comfortable. Complete the outfit with a statement belt or scarf for extra flair.
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Halter Dress with a Cashmere Sweater
Halter dresses can easily make the leap into fall with the right layering. Add a cozy cashmere sweater over the dress, leaving the halter neckline exposed.
The luxurious feel of cashmere paired with the flowing halter creates an elegant, effortless fall look.
Tulle Dress with a Faux Fur Jacket
A tulle dress, often seen in summer, can work wonderfully in the fall with a faux fur jacket. The playful volume of the tulle is offset by the chicness of the fur jacket, creating a fun yet sophisticated look.
Add boots and a clutch for a refined, winter-ready ensemble.
Maxi Dress with a Chunky Cardigan
Maxi dresses are incredibly versatile, and when layered with a chunky cardigan, they become perfect for cooler weather. The cardigan adds warmth without compromising the flow of the dress, making it both cozy and stylish.
Pair with sneakers or boots for a casual, everyday look.
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