2026 Fall Outfit Trends
From sweater dresses to pleated mini skirts with tights, these fall outfit ideas are made to mix, match, and layer on repeat. Try a sweeping maxi skirt with a belted jacket for a modern boho look, or layer a tie-front cardigan over your go-to mini with hosiery and boots for a polished finish. Add a statement sweater or bomber jacket to pull any look together. Rich tones like brown, burgundy, tan, and black keep every outfit sleek and autumn-ready.
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2025 Fall Outfit Ideas You Can Wear Now
Refresh your closet with new fall outfits and the latest dresses for fall from Windsor! Showcase your chic style in the cutest clothes, shoes, and accessories. Fall is the season for transitional clothing and stylish layering. Explore fall dresses in mini, midi, and long silhouettes to make for the perfect Thanksgiving outfits. Shop adorable sweater dresses, ruched dresses, romantic floral dresses, preppy plaid dresses, animal print dresses, and trendy dresses with marble or swirl print designs. Level up your Homecoming and holiday party looks with stunning dresses in satin, mesh, lace, velvet, crepe, or knit fabrications in new colors for 2025.
Get major outfit inspo with Windsor’s collection of fall clothes and the latest fall trends in women's fashion. Shop key neutrals as well as rich fall tones including burgundy, plum, hunter green, olive green, navy blue, oatmeal brown, and rust. Step up your casual looks with comfy sweaters that can be dressed up or down. Discover cropped sweaters, cardigans, long dusters, and relaxed-fitting sweaters in the coziest of fabrics that you'll love styling for work or school, a holiday party, or a bridal shower. Style with dark wash denim and ankle booties for the day, and faux leather leggings and combat boots for the night. Layer on trendy flannels and shackets to your everyday outfits to bring the chill vibes. Explore on-trend shackets with oversized fits and stylish plaid prints. For a bit of a dressier look, layer on fall jackets like fitted or oversized blazers, flowy dusters, or long trench coats.
No fall closet is complete without women’s jeans and the latest fall bottom trends! Go for skinny or flare jeans in a medium wash, dark wash, or black jeans to complement the fall season. Shop trendy jeans and denim skirts to create cute looks for back-to-school or college outfits. Style the latest skirts in soft knits, faux leather, and faux suede with your favorite fall tops. Plaid mini skirts are a major fall fashion staple. Pair your favorite skirts with crop tops, bodysuits, blouses, and sweaters. For a sleek and chic vibe, discover leggings, joggers, and pants in faux leather. These styles will instantly elevate any fall outfit. Style up your workwear with a cute paperbag and tie-waist pants with fitted or flared hems. Discover trendy jumpsuits and catsuits that will step up your fall style too! Shop streamlined catsuits perfect for nights out, and wide-leg jumpsuits for fall parties.
Complete your fall outfits with the best accessories. Shop on-trend boater hats, Panama hats, and cabby hats you can wear to fall festivals along with ankle booties, lug sole boots, or combat boots. Discover chain-link necklaces, hoop earrings, and sleek ring packs to glam up your autumn looks. Style your denim, skirts, and dresses with belts in classic, simple designs as well as with trendy statement buckles. For a polished look from head to toe, go for below-the-knee, knee-high, over-the-knee, and thigh-high boots to level up your fall shoe wardrobe. Find ankle boots with chains and cowboy boots to go with your favorite fall floral dresses. Keep all of your essentials on hand in the cutest clutches, handbags, and crossbody purses with quilted faux leather detailing. Windsor has the best selection of women’s fall fashion to create casual to dressy looks you’ll absolutely adore.
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Check Ya Later Plaid Flannel Shacket
This plaid flannel shacket will make you look effortlessly stylish! With long sleeves, button cuffs, and a classic collar neckline, you'll be the talk of the town. Featuring a button-down front, front pocket, and oversized silhouette, and is crafted on soft flannel woven fabric with a classic plaid print you'll adore this season. Style with sleek leggings and boots for the perf cold-weather fit'!
Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button-down front, pocket
- Oversized silhouette
- Soft flannel woven fabric
- Plaid print
- Runs true to size
Style Number/Barcode: 06204-1609
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Fall Vibes Belted Plaid Shacket
Layer on this trendy plaid flannel shacket for all the cozy fall vibes! It features a collared neckline, long sleeves, a complete button-down front, pockets, a tie-front belt to stylishly cinch your waist, and a relaxed fit. Pair with a basic bodysuit and a knit midi skirt.
Fit & Features
- Collared neckline, long sleeves, single button details
- Button-down front
- Buttoned chest pockets, faux side pockets
- Tie-front belt
- Relaxed fit
- Plaid print, woven flannel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1447
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Autumn Nights Plaid Cropped Shacket
This trendy plaid cropped shacket is perfect for those chilly autumn nights. It features a collared neckline, long sleeves, a complete button-down front, flap pockets, and a cinched elastic back. Layer over a long sleeve top and pair with your fave jeans for a cute and casual vibe.
Fit & Features
- Collared neckline
- Long sleeves, button cuffs
- Button-down front, Flap pockets with button closures
- Cropped hem with a cinched elastic back
- Plaid pattern
- Flannel woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1451
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Plaid's My Favorite Woven Shacket
It's the season for cozy layers and your favorite print! This plaid woven shacket features long sleeves, a collar neckline, button-down closures, a front pocket, and an oversized fit. Complete the look with matching bottoms.
Shop The Matching Bottoms: Plaid's My Favorite Woven Skirt
Fit & Features
- Long sleeves
- Collar neckline
- Button-down closures
- Front pocket
- Oversized silhouette
- Plaid pattern, woven fabric
- Fits true to size
Style Number/Barcode: 06204-1449
Category Name: 2026 Fall Outfit Trends
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever In Plaid Woven Skirt
They can find you forever in this plaid woven skirt all season! It features a high-rise waist, back zipper and hook-eye closure, a bodycon fit, and a mini-length hem. Complete the look in the matching shacket.
Shop Matching Ivory Shacket: Paint The Town Plaid Flannel Shacket
Shop Matching Taupe Shacket: Forever In Plaid Woven Shacket
Fit & Features
- High-rise waist
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Plaid pattern, non-stretch soft woven fabric
- Runs true to size
Style Number/Barcode: 06401-0635
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Forever In Plaid Woven Shacket
They can find you forever in this plaid woven shacket all season! It features cozy long sleeves with snap-button closures, a collar neckline, front snap-button closures, flap pockets, and a relaxed fit. Complete the look with the matching skirt.
Shop Matching Bottoms: Forever In Plaid Woven Skirt
Fit & Features
- Long sleeves with snap-button closures
- Collar neckline
- Front snap-button closures
- Flap pockets
- Relaxed fit
- Plaid pattern, non-stretch soft woven fabric
- Runs true to size
Style Number/Barcode: 06204-1452
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Knots Faux Wrap Mini Dress
You'll get tied up in knots for this elevated basic mini! It features a sleeveless, scoop neck, spaghetti straps, a bodycon silhouette, and an asymmetrical faux-wrap skirt with a knot accent. Complete the look in trendy sandals for a coffee date.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Bodycon silhouette
- Asymmetrical faux-wrap skirt
- Knot accent
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4661
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Options Open O-Ring Midi Dress
Keep your options open and wear this dress for your weekend plans! It features a sleeveless, v-neck, spaghetti straps, an open-back with an o-ring insert, a bodycon silhouette, and a midi hem on stretchy rib-knit fabric. Complete the look with chic heels.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Open-back, o-ring insert
- Bodycon silhouette
- Midi hem
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4659
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Swirls V-Neck Mini Dress
Perfectly swirled and smoothed to perfection! Showcase a head-turning look in this sleeveless mini dress featuring a v-neck, bungee spaghetti straps, bodycon silhouette, slit accent, and a marble print on brushed knit fabric. Complete the look in lace-up heels for a summer party.
Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Marble print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4660
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Babe Faux Suede Mini Dress
Step it up with a mini dress that showcases those trendy-chic vibes! It features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back lace-up design, a fitted high waist seam, and a short, form-fitting silhouette. Style with knee-high boots.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Cross-back, lace-up strappy design, tie closure
- Fitted high waist seam
- Mini-length, form-fitting silhouette
- Smooth faux suede fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4491
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always In Plaid Woven Crop Shacket
Don't be surprised if you find yourself wearing this plaid crop shacket on repeat! It features long sleeves with button cuffs, a collar neckline, a button-down placket, pockets, and a boyfriend silhouette. Complete the look in knee-high boots for a chic autumn outfit!
Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button-down placket, pockets
- Boyfriend silhouette
- Cropped hem
- Plaid pattern, flannel woven fabric
- Fits true to size
Style Number/Barcode: 06204-1454
Category Name: 2026 Fall Outfit Trends
Price: $21.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Plaid's My Favorite Woven Skirt
It's the season for cozy layers and your favorite print! This plaid woven skirt features a high-rise waist, back zipper closure, bodycon silhouette, and a mini-length hem. Complete the look with the matching shacket.
Shop The Matching Shacket: Plaid's My Favorite Woven Shacket
Fit & Features
- High-rise waist
- Back zipper closure
- Bodycon silhouette
- Mini-length hem
- Plaid pattern, woven fabric
- Fits true to size
Style Number/Barcode: 06401-0460
Category Name: 2026 Fall Outfit Trends
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love For Fall Plaid Cropped Shacket
Showcase your love for this cozy season with this on-trend cropped shacket. It features a collared neckline, long sleeves, a multi-button down front, and a cropped, cinched back hem. The flannel woven fabric features an all-over plaid print, perfect for the fall time. Layer over a bodysuit with faux leather pants for an elevated look.
Fit & Features
- Collared neckline
- Long sleeves, button details
- Multi-button down front
- Buttoned chest pockets
- Cropped hem with a cinched back
- Plaid print, flannel woven fabric
- Runs true to size
Style Number/Barcode: 06204-1450
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Cutout Mini Sweater Dress
This elevated mini sweater dress is a trendy staple for this fall season! It features a mock neckline, long fitted sleeves, waist cutouts that lead to the back, and a short, curve-hugging, bodycon silhouette. Style with strappy heels.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Waist cutouts that lead to the back
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1469
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hometown Girl Plaid Crop Shacket
This layer-ready plaid shacket is essential for building your perfect fall wardrobe! The crop shacket features long sleeves with buttoned cuffs, a collar neckline, button-down closures, flap pockets, and a trendy oversized fit. Complete the look in the matching skirt.
Shop The Matching Skirt: Hometown Girl Plaid Mini Skirt
Fit & Features
- Long sleeves, buttoned cuffs
- Collar neckline, flap pockets
- Button-down closures
- Oversized fit, cropped hem
- Plaid pattern
- Brushed woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1446
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Neutral Tie-Dye Mini Dress
You'll fall in love with the trendy neutral tones of this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back, lace-up design, and a short, curve-hugging fit. The soft brushed knit fabric offers plenty of stretch. Style with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cross-back, lace-up design, tie closure
- Mini-length, form-fitting silhouette
- Neutral tie-dye pattern
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4645
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off The Grid Plaid Woven Shacket
Preppy and stylish, stay ahead of the trend and rock this plaid woven shacket featuring long sleeves with buttoned cuffs, a collar neckline, six-button down front closures, flap pockets, and an oversized silhouette. Complete the look in a basic bodysuit and skirt.
Fit & Features
- Long sleeves, buttoned cuffs, collar neckline
- Six-button down front closures
- Flap pockets
- Oversized silhouette
- Plaid houndstooth pattern
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1443
Category Name: 2026 Fall Outfit Trends
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Your Favorite Crop Denim Shacket
Effortlessly laid back and cool, your favorite crop denim shacket to layer over your cutest daily fits! It features long sleeves with button cuffs and trendy distressed accents, a collar neckline, snap button-down closures, flap pockets, and a relaxed, curved hemline. Complete the look in a cute casual dress.
Fit & Features
- Collar neckline
- Long sleeves, button cuffs, distressed accents
- Snap button-down closures
- Flap pockets
- Relaxed fit, curve crop hemline
- Light wash non-stretch denim
- Runs true to size
Style Number/Barcode: 06203-0475
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Collar neckline
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Casual Fall Days Flannel Shacket
Layer on this trendy flannel shacket for those casual fall days! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, a relaxed fit, and an all-over plaid print. Style with a basic bodysuit, denim, and combat boots.
Fit & Features
- Collared neckline
- Long sleeves, buttons to cuff
- Button-down front
- Buttoned chest pockets
- Relaxed fit
- Plaid print, woven flannel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1444
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Pick Floral Mini Dress
This adorable floral mini dress is the cutest pick for the summer season! It features a sleeveless square neckline, bungee spaghetti straps, ruched detailing down the side seams, a short, form-hugging fit, and an all-over daisy print. Style with a denim jacket and sneakers.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruching down the side seams
- Mini-length, form-fitting silhouette
- Small daisy floral print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4641
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Cropped Denim Trucker Jacket
Layer on the casual vibes with this vintage-inspired cropped denim trucker jacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, side pockets, and a cropped fit. Style over a basic tee with distressed jeans.
Fit & Features
- Collared neckline
- Drop shoulder design, long sleeves, single button detailing
- Button-down front
- Buttoned chest pockets, side pockets
- Cropped
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0473
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Extra Cropped Denim Jacket
You love being extra! This cropped denim jacket is a must-have statement piece for your wardrobe. Featuring a collared neckline, long sleeves, a button-down front, and an all-over newspaper print pattern, this jacket will have all eyes on you. Style with a basic bodysuit and a bodycon mini skirt.
Fit & Features
- Collared neckline
- Long sleeves, single buttons to cuff
- Button-down front, chest pockets
- Cropped hem
- Newspaper print
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0470
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Perfection Knit Mini Dress
This adorable ribbed knit mini dress is perfect for everyday styling! It features a collared V-neckline, short sleeves, center ruched detailing with an adjustable drawstring at the hem, and a short, form-hugging fit. Complete the look with heeled mules.
Fit & Features
- Collared V-neckline
- Short fitted sleeves
- Center ruching, adjustable drawstring at the hem
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4636
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chill Temps Plaid Crop Shacket
When the temps are starting to chill you'll be reaching for this plaid crop shacket to keep cozy and cute! The shacket features long sleeves with button cuffs, a collared neckline, front button-down closures, flap pockets, and a relaxed fit. Complete the look in a basic bodysuit and jeans for a casual hang.
Fit & Features
- Long sleeves with button cuffs
- Collared neckline
- Front button-down closures
- Flap pockets
- Cropped hem, relaxed fit
- Plaid pattern, non-stretch woven fabric
- Fits true to size
Style Number/Barcode: 06204-1436
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale