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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Taylor High Rise Skinny Crop Jeans By Windsor Denim
Achieve an hourglass appearance in the Taylor High Rise Jeans by Windsor Denim! Put your curves on display in her flattering high-rise waist, skinny-leg design with a raw hem and light distressed accents. The jeans are composed of a Lycra-cotton blend denim fabric with stretch and shape retention. Complete the look in a chic top and heels.
Fit & Features
- High-rise waist
- Light distressed accents
- Skinny-leg design, raw crop hem
- Front button and hidden zipper closure
- 5-pocket styling, belt loops
- Lycra-cotton blend denim, minimal stretch
- Fits true to size
Style Number/Barcode: 06602-0338
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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Love This Mid-Rise Flare Denim Jeans
Give your closet a bit of love by adding in these mid-rise denim jeans to mix things up! They feature a mid-rise waist and a hip-hugging silhouette that leads to the flare leg hem. The premium denim fabric offers a moderate stretch for comfortable wear. Complete the look in a cute crop cardigan.
Fit & Features
- Mid-rise waist
- Hip-hugging
- Flare leg hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loops
- Premium denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0373
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Casual Long Sleeve Crop Top
This long sleeve crop top is the cozy casual staple for the season! It features a V-neckline, long dolman-style sleeves, a cropped hem, a relaxed fit, and is composed of a wide ribbed knit fabric. Style this cute crop top with a mini skirt and ankle booties.
Fit & Features
- V-neckline
- Long dolman sleeves
- Cropped hem
- Relaxed fit
- Wide ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-2281
Category Name: 2026 Fall Outfit Trends
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High-Rise Distressed Boyfriend Jeans
Create a dramatic moment with distressed jeans that add an edge to your look! The medium-wash denim jeans feature a flattering high-rise waist and a boyfriend silhouette with trendy knee slits. Complete the look with a crop top and combat boots.
Fit & Features
- High-rise waist
- Boyfriend silhouette
- Knee slit accents
- Multi-button down closures
- Five-pocket styling, belt loop accents
- Medium-wash denim, slight stretch
- Runs true to size
Style Number/Barcode: 06602-0240
Category Name: 2026 Fall Outfit Trends
Price: $42.90
Availability: In Stock
Available Color: MEDIUM, DENIM
Available Size: 1, 3, 5, 7, 9, 11, 13
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Forever Fashionista Mini Skirt
Shop Matching Top: Forever Fashionista Crop Top
You're a forever fashionista kinda girl, and this leopard print mini skirt is a must for you. It features a high rise waist, a small front slit, and a slim, A-line fit. The soft knit fabric offers moderate stretch and a form hugging fit. Complete your chic look with the matching crop top!
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06501-0160
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Two Moods Reversible Bomber Jacket
Who says you have to stick to one mood all the time? This jacket allows you to switch it up if you like! Designed to be reversible, this jacket features a mock neckline, traditional pockets at the sides- both inside and out, a zipper breast pocket, also on both sides, a zipper closure down the center, and a mid waist hem with an adjustable drawstring. One side is composed of a nylon material, and one side is composed of a sherpa offering a relaxed fit and no stretch.
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06201-0015
Category Name: 2026 Fall Outfit Trends
Price: $20.97 $54.90
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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Taking Knit To The Next Level Sleeveless Catsuit
Elevate your night out with a catsuit that strikes a glam vibe. The catsuit features a sleeveless square neckline, a sexy midriff cut out, sleek spaghetti straps, and a fitted skinny leg with a tapered hem. The catsuit is composed of a brushed knit fabric that offers a form hugging fit. Complete look with clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Midriff cutout
- Skinny leg fit with a tapered hem
- Brushed knit fabric
- Form hugging fit
Style Number/Barcode: 06502-0452
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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Sleek Strapless Satin Jumpsuit
Create a sleek and chic look in this strapless satin jumpsuit. It features a straight-across neckline, a high-rise cinched elastic waistband, side pockets, and relaxed-fitting pant legs with a tapered jogger hem. Take this look from day to night by layering on a faux leather jacket and pairing it with strappy heels.
Fit & Features
- Strapless straight-across neckline, elastic band
- High-rise cinched waist, elastic band
- Side pockets
- Relaxed-fitting pant legs, tapered jogger hem, elastic band
- Satin fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-0401
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leopard Bell Sleeve Chiffon Mini Dress
This is one for our boho babe! This flowy dress features a v-neckline that meets a knot accent and keyhole cut out at the center of the bodice. Dress has long sleeves that are smocked mid way and flare into a bell style. Skirt meets bodice mid waist and has a flow to it which makes it easy to move around in. Fully lined with a hidden zipper below arm.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0377
Category Name: 2026 Fall Outfit Trends
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Purrfect Look Leopard Print Top
Get a purrfect look in this sassy chic leopard print top! Pair with some high rise black denim shorts and strappy mules and get ready to go to happy hour with your girls!
Fit & Features
- Long cuffed billowy sleeves
- Deep V neckline
- Tie front detail
- Cropped
- All over leopard print
- Wool dobby woven fabric
Style Number/Barcode: 06204-0389
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Rise Destructed Mom Jeans
Keep on trend with mom jeans with standout deets! The jeans feature a high rise waist, heavy destruction throughout, and a cropped hem. Complete your look with a cute crop top!
Fit & Features
- High rise waist
- Single-button and zipper closure
- Traditional five-pocket and zipper closure
- Heavy destruction throughout
- Cropped hem
- Dark wash denim fabric
Style Number/Barcode: 06602-0195
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Making Moves Platform Block Heels
Make some major style moves in these booties. The booties feature an around the ankle fit, a lace-up front, an almond toe with a wide platform, and a block heel. The booties are composed of a faux leather material. Complete look with a bodycon dress.
Fit & Features
- Around the ankle fit
- Lace-up front
- Almond toe
- Wide platform
- Block heel
- Faux leather material
Style Number/Barcode: 07403-0618
Category Name: 2026 Fall Outfit Trends
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paisley Chic Lace Up Crop Top
Show off your boho side with a cute crop top that is perf for festival season! The top features a paisley print, a sleeveless square neckline, spaghetti straps that lead to a cross back, lace-up straps, and a cropped hem. The top is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching pants.
Shop Matching Pants: Paisley Chic High Waist Pants
Fit & Features
- Sleeveless square neckline
- Spaghetti straps, cross back
- Lace-up back
- Paisley print
- Cropped hem
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06001-3500
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Charm Cropped Knit Cardigan
Cozy and charming, this knit cardigan offers a classic design with a button-down front for versatile styling options and a cropped hem.
Fit & Features
- Knit fabrication, moderate stretch
- Button-down front
- Long sleeves
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2153
Category Name: 2026 Fall Outfit Trends
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple Chic Block Heel Booties
These simple chic block heel booties will go with all of your stylish 'fits! They feature a pointed toe, an ankle-high design, an inner zipper closure, and a short block heel. Pair these booties with dark wash jeans and a cropped sweater.
Fit & Features
- Pointed toe
- Ankle-high design
- Inner zipper closure
- Short block heel
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07403-1324
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Days Faux Fur Plaid Shacket
You'll have so many cozy days in this cute faux fur plaid shacket perfect for the chilly season! It features comfy long sleeves, a collar neckline, a button-down front, front flap pockets with button closures, and a relaxed fit. Complete the look in trendy booties for casual plans!
Fit & Features
- Long sleeves
- Collar neckline
- Button-down front
- Front flap pockets, button closures
- Relaxed fit
- Plaid pattern, faux fur fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0396
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total It Girl Belted Trench
Be a total it girl with this chic and sophisticated belted trench! It features long fitted sleeves, a front flowy lapel collar, an elastic banded back, and a tie front belt. The jacket is composed of a lightweight woven fabric that offers a relaxed fit with no stretch.Style Number/Barcode: 06204-0203
Category Name: 2026 Fall Outfit Trends
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Floral Ruched Knit Mini Skirt
Impress this season in a floral skirt. Dress up your basic tops with a floral mini skirt that features a flattering high rise waist, ruched side seams with drawstring ties, and an all-over floral print. The skirt is composed of a smooth knit fabric that enhances curves with a moderate stretch. Complete your outfit with strappy heels and a dainty necklace for a daytime look.
Fit & Features
- High rise waist
- Ruched side seam with drawstring ties
- Floral print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 06501-0262
Category Name: 2026 Fall Outfit Trends
Price: $8.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Waist Linen Cargo Pants
Keep it sleek and stylish with these cargo pants! The pants feature a high-rise waist, an adjustable belt with a D-ring buckle, slanted pockets, cargo pockets, and a tapered hem. The pants are composed of a linen fabric that offers a form-hugging fit. Complete look with a bodysuit.
Fit & Features
- High-rise waist
- Adjustable belt with D-ring buckle
- Hidden front zipper and dual hook and bar closures
- Slanted pockets, cargo pockets
- Tapered hem
- Linen fabric, form-hugging fit, no stretch
- Runs true to size
Style Number/Barcode: 06302-0287
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Lace-Up Over-The-Knee Boots
Get a luxe look this season with these chic faux suede over-the-knee boots. They feature a closed pointed toe, an on-trend lace-up front design, an inner zipper closure, and a block heel. Style these boots with a plaid skirt and a cropped sweater.
Fit & Features
- Over-the-knee fit
- Closed pointed toe
- Lace-up front
- Partial inner zipper closure
- Block heel
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07402-0764
Category Name: 2026 Fall Outfit Trends
Price: $17.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Trendy Vibe Lug Sole Booties
Bring on the trendy vibes with these edgy-chic booties! They feature an above the ankle fit with a round toe, elastic gore details, a lug sole, and a chunky block heel. The patent faux leather material has an all-over textured design. Style these booties with your fave pair of denim.
Fit & Features
- Above the ankle fit
- Round toe
- Elastic gore details
- Lug sole
- Block heel
- Patent faux leather material, textured design
- Runs true to size
Style Number/Barcode: 07403-1346
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fly By Satin Butterfly Crop Top
Whimsical and sleek, this satin crop top will inspire you to spread your wings! It features peasant long sleeves, a sweetheart neck, a stretchy smocked back, and a twisted cropped hem. The top is composed of an abstract butterfly print on non-stretch satin fabric. Style with the matching bottoms.
Shop Matching Bottoms: Fly By Satin Butterfly Midi Skirt
Fit & Features
- Peasant long sleeves
- Sweetheart neck
- Stretchy smocked back
- Twisted cropped hem
- Abstract butterfly print
- Non-stretch satin fabric
- Runs true to size
Style Number/Barcode: 06003-2136
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Style Points Knit Block Heel Booties
You'll be raking major style points in these ankle booties featuring a pointed toe, and a block heel, and are crafted from a knit material. Complete the look with a mini handbag and coat for work or play!
Fit & Features
- Pointed toe
- Block heel
- Ankle-length shaft
- Knit material
- Runs true to size
Style Number/Barcode: 07403-1653
Category Name: 2026 Fall Outfit Trends
Price: $12.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free