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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Kailey High Rise Bermuda Shorts
Oasis by Eunina
Channel chic vibes in shorts that are anything but basic! The shorts feature a high rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, and a Bermuda length. Complete look with a sleek bodysuit and strappy sandals.
Fit & Features
- High rise waist
- Single-button with zipper closure
- Traditional five-pocket with belt loop design
- Bermuda length with fringed hem
- Light-medium acid wash
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06603-0144
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Faux Suede Block Heel Booties
Get stacked on these cute booties that bring the glam to your favorite layered looks! The booties feature an around the ankle fit, lace-up detail at the back with metal grommets, and a stacked block heel. Booties are composed of faux suede material. Complete look with a chunky sweater.
Fit & Features
- Around the ankle fit
- Lace-up detail at the back with metal grommets
- Stacked block heel
- Almond toe
- Inner zipper closure
Style Number/Barcode: 07403-0344
Category Name: 2026 Fall Outfit Trends
Price: $22.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Move Biker Shorts
Keep on the go in biker shorts that nail that effortlessly casual vibe down. The biker shorts feature a high rise waist and a mid-thigh length. Complete your look with a casual crop top and chunky dad sneakers for your next coffee run.
Fit & Features
- High rise waist
- Mid-thigh length
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Model is 5'9" with 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06503-0165
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Step Up Camo Lug Sole Booties
Step up in camo booties that command attention this season. The booties feature an around the ankle fit, goring accent at the back of the ankle, a trendy camo print, lug sole, and a block heel. Complete your look with a black mini skirt and basic bodysuit.
Fit & Features
- Around the ankle fit, goring accent at the back of the ankle
- Camo print
- Lace-up front with small metal grommets
- Inner zipper closure
- Round toe
- Lug sole, block heel
- Canvas material
Style Number/Barcode: 07403-0343
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lace Trim Knit Biker Shorts
Get on the biker short trend with this chic lace trim version! They feature a flattering high rise waist with a mid-thigh hem and pretty lace trim. Pair with a crop top and a tapered blazer for a cute happy hour look with the girls.
Fit & Features
- High rise waist
- Mid-thigh length
- Sheer lace trim
- Curve-hugging fit
- Knit fabric with a pretty sheen
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06503-0163
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute And Cozy Ribbed Knit Romper
Keep it cute and cozy in this adorable ribbed knit romper. Featuring a deep V neckline and tie front detail at the waist, this romper would be so cute paired with chunky sneakers. Wear to a movie night with your squad!
Fit & Features
- Short sleeves
- Deep V neckline
- High waist
- Tie front detail
- Ribbed knit fabric
Style Number/Barcode: 06503-0164
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Nylon Faux Fur Reversible Jacket
Amp up your trendy style with this of the moment reversible jacket! It features a sleek nylon fabric on the outside and a soft faux fur fabric on the interior. Layer this jacket over a pair of biker shorts for that casual chic everyday vibe.
Fit & Features
- Collared
- Long sleeves
- Complete zip front
- Drawstrings at hem
- Nylon exterior with thin striped detailing
- Faux fur interior with large front pocket
Style Number/Barcode: 06201-0111
Category Name: 2026 Fall Outfit Trends
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Minimal Moment Thin Block Heels
Keep it minimal in heels that simply go with everything. Dress up your casual outfits with these fab heels. The heels feature an adjustable ankle strap, an open almond toe with a single strap over the toe, and a sleek thin block heel. Complete your look with a ribbed midi dress and blazer.
Fit & Features
- Adjustable ankle strap
- Open almond toe
- Single strap over the toe
- Thin block heel
Style Number/Barcode: 07401-2407
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched V Neck Jersey Knit Crop Top
Style up this adorable ruched jersey knit crop top for a cute everyday 'fit! It features a flattering V neckline and a ruched form-hugging look. Pair this top with gold tube hoop earrings to give yourself a trendy vibe.
Fit & Features
- V neckline
- Long fitted sleeves
- Ruched front detailing
- Cropped hem
- Form-hugging fit
- Jersey knit fabric
Style Number/Barcode: 06001-2843
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All About Knit Mock Neck Mini Dress
You'll be totally all about this chic mock neck mini dress! Featuring long fitted sleeves and a curve-hugging fit, this dress is perfect for the fall season. Pair with gold hoop earrings and chunky sneakers for that fab everyday 'fit.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Short, form-hugging fit
- Knit fabric
Style Number/Barcode: 05102-0855
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Destructed Cargo Joggers
Keep it casual in cargo joggers that nail that effortlessly put-together look. The denim joggers feature a high rise waist, heavy destructed detail, cargo-styled pockets, and cropped hem with elastic cuff. Complete your look with a crop top and chunky sneakers.
Fit & Features
- High rise waist
- Single-button with zipper closure
- Traditional five-pocket with belt loop design
- Cargo-styled pockets
- Heavy destructed detailing
- Jogger-like fit with cropped elastic cuff
- Relaxed fit, runs true to size
Style Number/Barcode: 06602-0233
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Suede Platform Lace-Up Booties
Elevate your chic everyday style with these faux suede booties! They feature a chunky platform and an adorable lace-up back detail. Pair these booties with dark wash skinny jeans for an elongated look.
Fit & Features
- Ankle-high design
- Almond toe
- Inner zipper closure
- Chunky platform
- Tall block heel
- Lace-up back detail
- Faux suede material
Style Number/Barcode: 07403-0345
Category Name: 2026 Fall Outfit Trends
Price: $20.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Waist Wild Thing Leggings
Show off your wild side in these leggings that wow. These leggings feature a high rise waist, a trendy animal print, and a skinny leg fit with a tapered hem. Pair your leggings with a crop top and sporty sneakers.
Fit & Features
- High rise waist
- Trendy animal print
- Side pocket
- Skinny leg fit
- Tapered hem
- Faux leather fabric
- Form hugging fit
Style Number/Barcode: 06502-0405
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Belted Cargo Joggers
Keep your look trendy in these of the moment belted cargo joggers! They feature a flattering high-rise fit with a cool buckle belt detail and cargo-style pockets. Pair with a simple bodysuit and accessorize with some chunky gold hoop earrings for that casual chic vibe.
Fit & Features
- High-rise waist
- Buckle belt
- Cargo-style side pockets
- Jogger hem with button detailing
- Woven fabric
- Runs true to size
Style Number/Barcode: 06302-0158
Category Name: 2026 Fall Outfit Trends
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ally High Rise Destructed Mom Jeans
Oasis by Eunina
The Ally High Rise Destructed Mom Jeans will elevate your look for sure. With their flattering high waist fit and distressed detailing, they can easily be dressed up or down. Pair with a chic sheer sleeved blouse and strappy heels for a cute brunch look.
Fit & Features
- High rise waist
- Traditional five-pocket and belt loop design
- Front button closure
- Destructed detailing on the front
- Denim fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size three.
Style Number/Barcode: 06602-0181
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Ponte Knit Flare Pants
Create a figure-flattering curve-hugging silhouette in these ponte knit pants! They feature a high rise waist with a flared out hem. Pair these classic pants with a basic form-fitting bodysuit and a layered gold necklace for a casual night out look.
Fit & Features
- High rise waist
- Belt loops
- Front button closure
- Two back pockets
- Form-hugging fit
- Flared hem
- Ponte knit fabric
Style Number/Barcode: 06502-0404
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Point Lace Up Stiletto Booties
Lace-up in chic booties to keep your look on point! Perfect for your next GNO or your next date night with bae. The booties feature a trendy lace-up front to create a customized fit, a pointed toe, and a sleek stiletto heel. Complete your look with a sweater dress and moto jacket.
Fit & Features
- Around the ankle fit
- Lace-up front
- Inner zipper closure
- Pointed toe
- Stiletto heel
- Faux microsuede material
Please be advised that these booties run small. Fit model recommends sizing one size up.
Style Number/Barcode: 07403-0318
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wildly Fierce Faux Suede Stiletto Booties
Step out in these wildly fierce booties for your next girl's night out or for your next date night with bae! The booties feature an around the ankle fit, a lace-up front, wildly-inspired leopard print, and a sleek stiletto heel. Complete your look with dark wash denim jeans and a bustier.
Fit & Features
- Around the ankle fit
- Lace-up front
- Inner zipper closure
- Pointed toe
- Leopard print
- Sleek stiletto heel
- Faux microsuede material
Style Number/Barcode: 07403-0319
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lace Up Faux Nubuck Stiletto Booties
Lace-up in these chic booties this season as you head out to grab a PSL or to go with your back to school outfit! The booties feature a trendy pointy toe, a lace-up front with small grommets, and a sleek stiletto heel. Complete your look with a cute cardigan and high waist skinny jeans.
Fit & Features
- Around the ankle fit
- Lace-up front with small grommets
- Pointed toe
- Stiletto heel
- Faux nubuck material
Style Number/Barcode: 07403-0316
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fancy Gal Tassel Crossbody Bag
You're a fancy gal at heart and will love this tassel crossbody bag! It features a chic quilted design and comfortable crossbody chain. Pair with your favorite jeans and basic top to elevate your look!
Fit & Features
- Rectangular shape | Quilted design
- Top zipper closure
- Tassel accent
- Removable crossbody chain strap
Style Number/Barcode: 07203-0385
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Over The Knee Open Toe Block Heeled Boots
Slay each and every step in these sultry over the knee block heeled boots! They feature an open toe detail and a smooth faux suede fabric. Wear these with your fave faux leather mini skirt for an edgy-chic vibe for date night.
Fit & Features
- Open toe detail
- Block heel
- Inner zipper closure
- Over the knee design
- Back tie closure
- Faux suede fabric
Style Number/Barcode: 07402-0186
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Into You Basic Knit Midi Dress
We're so into this dress that can be dressed up for a date night or keep it casual with layers. The dress features a sleeveless square neckline, tank-straps that offer support, and a curve-hugging midi-length silhouette. Complete look with ankle booties or mules.
Fit & Features
- Sleeveless square neckline
- Tank straps
- Midi length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0912
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek and Chic Lace Up Stiletto Booties
Lace-up in sleek booties for your next night out to make a stylish statement! The booties feature an around the ankle fit, a lace-up front with small grommets, a pointed toe, and a low stiletto heel. Complete your outfit with a trendy sweater dress and door knocker earrings.
Fit & Features
- Around the ankle fit
- Lace-up front with small grommets
- Inner zipper closure
- Pointed toe
- Low stiletto heel
- Faux nubuck material
Style Number/Barcode: 07403-0317
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feelin' Fierce Leopard Print Stiletto Booties
Yes babe, these leopard print stiletto booties will make you as fierce as can be! Slay each step in these booties that feature a trendy pointed toe and all over wild leopard print. Pair with a classic little black dress and a gold necklace for the perf date night in vibe.
Fit & Features
- Pointed toe
- Elastic detail on each side
- Back zipper closure
- Stilleto heel
- Leopard print
Style Number/Barcode: 07403-0315
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale