25 Comfortable Fall Transition Outfits That Are Easy to Copy

Dressing for those in-between days when it's not really Summer anymore but not quite Fall yet can be a real nightmare. If you're panicking about finding a comfy outfit for those transitional months, we've got you covered. Ahead, we found fresh and stylish ways you can continue to wear your favorite Summer staples well into the cooler months. Read on to see 25 comfortable Fall transitional outfits you'll be wearing on repeat.

01
Cutout Sundress
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Cutout Sundress

Wear two of your favorite Summer pieces in the cooler months by styling them together. Layer your striped button-up under a cutout sundress, and finish your look with a hat.

02
Summer Dress
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Summer Dress

Flowy Summer dresses are some of the easiest pieces to wear during the transitional season. Choose a midlength dress and style it with a long coat and a pair of closed-toe wedges to make it Fall-appropriate.

03
Dad Sneakers
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Dad Sneakers

If you're confused on whether it's time to put away your dad sneakers, don't. You can continue to wear your comfy sneakers with vintage jeans and a long plaid coat to tie your look together.

04
Pleated Skirt
Getty | Matthew Sperzel

Pleated Skirt

Midi skirts are some of the most versatile pieces a woman can own. Show off just the right amount of skin by styling one with a sweater, ankle boots, and a chic coat thrown over your shoulders.

05
Floral Mini
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Floral Mini

The key to dealing with the transitional weather is layering. You can wear a floral minidress in the Fall by styling it with a worn-in leather jacket, comfortable tights, and a cozy scarf.

06
Silk Slip Dress
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Silk Slip Dress

There's something so effortless about a silk slip dress. Pair it with your softest turtleneck sweater and comfy black boots.

07
Vacation Prints
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Vacation Prints

Make your vacation-print tops and jackets Fall-appropriate by styling them with long pants. If you want to add another trend, slip into a pair of dad sneakers.

08
Plaid Shirt
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Plaid Shirt

Take your coziest plaid shirt and use it as a jacket. Layer a hoodie underneath it for added warmth.

09
Flowy Dress
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Flowy Dress

There's nothing comfier than a flowy dress. Layer a long-sleeved top underneath it, and style it with statement earrings.

10
Sweatpants
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Sweatpants

One of the most comfortable outfits to wear is sweatpants and a hoodie. Give your look a Fall twist by throwing on a tweed coat over your tracksuit.

11
Denim on Denim
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Denim on Denim

Denim on denim is one of the easiest looks to pull off during the transitional season. Style your worn-in jacket with your favorite pair of baby blues and leather boots.

12
Low-Top Sneakers
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Low-Top Sneakers

Wear your cropped jeans with a black bucket bag, a fuzzy zip-up, and sneakers.

13
LWD
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LWD

Who says you have to put away your LWD after Labor Day? All you have to do is throw a trench coat over it and wear a pair of block heels.

14
Striped Blouse
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Striped Blouse

Get the most out of your blue and white striped blouse by styling it with a Fall staple: a leather midi skirt.

15
White High-Top Sneakers
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White High-Top Sneakers

You can continue to wear your stark white high-tops in the Fall by styling them with a plaid dress and colorful coat in case it gets chilly.

16
Jean Jacket
Getty | Christian Vierig

Jean Jacket

Throw a sweatshirt on under your denim jacket for extra warmth.

17
Summer Shorts
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Summer Shorts

On warmer days, take out your Summer shorts and style them with a long-sleeved shirt and mules.

18
Denim Skirt and Boots
Getty | Christian Vierig

Denim Skirt and Boots

Slip into a pair of snakeskin booties to ground your denim miniskirt and white blouse.

19
Monochrome
Getty | Christian Vierig

Monochrome

Match your cropped light pink pants with a cozy turtleneck sweater.

20
Deconstructed Denim
Getty | Matthew Sperzel

Deconstructed Denim

Wear your lightweight striped shirt with deconstructed denim and white Converses.

22
Miniskirt
Getty | Edward Berthelot

Miniskirt

You can continue to wear your miniskirt on warmer days of the season by styling it with a tie-dye sweatshirt.

23
White T-Shirt
Getty | Timur Emek

White T-Shirt

Keep wearing the classic white tee and jeans combo by simply adding a long trench coat.

24
Summer Flats
Getty | Claudio Lavenia

Summer Flats

An easy way to show off your comfortable Summer flats is by styling them with a pair of cuffed jeans. Finish your look with a chunky turtleneck sweater to keep the breeze at bay.

25
Denim Skirt
Getty | Timur Emek

Denim Skirt

An easy styling hack for this Summer staple is to throw on a pair of black tights underneath. You can style your denim skirt with a pair of stark white booties and an oversize blazer to make your look feel less casual.