Transitional Dresses for Fall

Go From Summer to Fall to Winter Seamlessly

12.07.23

By Rebecca Byatt

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The end of summer is coming and we’re ready to welcome the fall in all its orange glory. We’ve found ourselves at that in-between period where it’s still too warm for a winter coat and scarf, but too cold for a jacketless look. Enter transitional dressing. Perfect for when you’re not too sure what weather mother nature is going to throw at you. A staple in trans-seasonal dressing? The strategic fall dress. Basically, opting for dresses for the fall that you can wear with sandals in the summer, then layer with a sweater in winter, and style with tights and boots on those chillier days.

At Nasty Gal we’ve picked our best fall to winter dresses to help you build your transitional closet, for whatever occasion and whatever weather it brings.

Fall to Winter Maxi Dresses

The maxi dress has been a staple in recent months, and we’re not letting go of it just yet. With a few minor adjustments, it can transition seamlessly into your winter closet. Whilst a long sleeve fall maxi dress is the obvious choice to keep you warm as the temperatures drop, if you also opt for a lighter fabric such as chiffon or mesh, it will double up for those warmer days. This season we love a fall maxi dress with darker, blown out florals, eye-catching prints, and metallic detailing.

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Knitted High Neck One Sleeve Maxi Dress
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Contrast Stripe Button Knitted Maxi Dress
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Body Print Long Sleeve Maxi Dress
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Ribbed Knit Bandeau Maxi Dress
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Plus Size Heart Tiered Maxi Dress
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Spot Chiffon Print Pleated Maxi Dress
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Cotton Paisley Border Print Halter Maxi Dress
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One Shoulder Knit Maxi Dress
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Fall to Winter Cocktail Dresses

For those heavily anticipated social events, a fall cocktail dress will be needed. Although a classic cocktail dress is timeless enough to see you throughout the seasons anyway, with a little styling magic, you can make it winter-appropriate. Pair your LBD with closed toe stilettos rather than heeled sandals, semi sheer tights, and an oversized blazer, and you’re ready for any evening event in your November-January calendar.

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Premium Bandage Side Split Midi Dress
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Sequin Lace Up Back Midi Dress
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Animal Print Chiffon Long Sleeve Maxi Dress
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Floral Print Satin Cut-Out Maxi Dress
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Plunging V-Neckline Split Midi Dress
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Bardot Split Hem Midi Dress
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Satin Column Open Back Midi Dress
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Faux Leather Fringed Longline Blazer
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Pinstripe Pocket Detail Tailored Blazer
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Long Sleeve Dresses for Fall and Winter

The failsafe transition from fall to winter is switching up your tank for a long sleeve, and fall dresses are no exception. When choosing a long sleeve fall dress, opt for cut-out detailing, a fitted waistline, ruching, or a thigh split to balance your silhouette, to still give definition to your curves. We love to style these fall dresses with chunky boots, sheer tights, and an oversized leather jacket in winter (if the weather warrants it).

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Animal Print Bardot Asymmetric Long Sleeve Dress
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Shadowed Floral Cutout Long Sleeve Mini Dress
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Lace Crew Neck Long Sleeve Mini Dress
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Mono Low Back Long Sleeve Midi Dress
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Tie Waist Tailored Blazer Dress
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Plus Size Long Sleeve Open Back Crochet Maxi Dress
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Plated Knit Cut Out Long Sleeve Mini Dress
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Fall to Winter Midi Dresses

A fall midi dress is a trans-seasonal staple in our closet. Take your midi dress from AM to PM simply by switching up your accessories. Dress down with chunky boots and an oversized leather jacket for work or a shopping trip, and dress up with heels and embellished jewelry for cocktails with girlfriends. When shopping for midi dresses appropriate for fall and winter, opt for florals, fun prints, and flattering silhouettes like columns, fit and flares, and figure hugging fits.

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Petite Satin Column Open Back Midi Dress
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Plus Size Floral Pleated Midi Dress
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Crossed Back Tie Detail Printed Midi Dress
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Bardot Fold Over Ribbed Knitted Midi Dress
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Petite Velvet Cami Midi Dress
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Ruched Side Floral Print Midi Dress
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Plus Size Tiger Wrap Midi Dress
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Flocked Mesh Cowl Neck Midi Dress
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Casual Fall to Winter Dresses

We’ve also got you covered for those more casual occasions. Whether it’s a brunch date with friends, weekend walk, or maybe an after work date – our cute fall dresses will have you looking your best while keeping you cozy and comfortable. Style an oversized hoodie or t-shirt as an alternative for a transeasonal look, which is perfect for an early morning coffee run or college lecture.

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Zip Through Short Sleeve Denim Mini Dress
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Cluster Sequin Slouch Shift Dress
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Plus Cluster Sequin Slouch Shift Dress
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Oversized Denim Button Shirt Dress
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Acid Wash Off Shoulder Slogan Top
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Plus Size Floral Ruched Skater Dress
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Sweetheart Neckline Animal Print Puff Sleeve Midi Dress
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Ribbed Corset Detail Knit Mini Dress
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Loving the fall content? Check out our seasonal blog posts below

Shop all Fall Outfits & Winter Outfits at Nasty Gal.