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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Happy Hour Approved Tie-Front Blazer
This chic woven blazer is totally happy hour approved! It features a classic lapel collar, long sleeves with shoulder pads for structure, a tie-front design creating a V-neckline, and a cropped, fitted silhouette, The smooth woven fabric has no stretch. Style with faux leather pants and strappy mules for drinks with the girls.
Fit & Features
- Lapel collar
- Long sleeves, button details at the hem
- Shoulder pads
- Tie-front, V-neckline
- Cropped hem, fitted silhouette
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1490
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stretch The Rules Mesh Denim Print Crop Top
Stretch the rules in this Y2K-inspired mesh crop top perfect for concerts and backyard parties! It features fitted long sleeves, a mock neck, and a fitted hem on denim printed sheer mesh fabric. Complete the look with a seamless bralette and your favorite bottoms!
Fit & Features
- Fitted long sleeves
- Mock neck
- Fitted crop hem
- Denim print
- Sheer mesh fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06002-1643
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Buckle Up High Rise Cutout Flare Denim Jeans
Get ready for these edgy denim jeans to enter your closet! They feature a Y2K-inspired design with a flattering high-rise waist, side cutouts with adjustable straps and buckle closures, a hip-hugging fit, and a flared hem on premium denim fabric. Complete the look with a cute crop tee for a concert or movie with friends!
Fit & Features
- High-rise waist
- Side cutouts, adjustable straps, buckle closures
- Back zipper and hook-eye closure
- Hip-hugging fit
- Flared hem
- Premium denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06602-0450
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trish Mid-Rise Cargo Wide-Leg Jeans By Windsor Denim
The Trish cargo jeans by Windsor Denim are the perfect base for easy outfit styling! Love your on-trend look in these flattering mid-rise jeans featuring a wide-leg silhouette with cargo-style pockets and seam detailing for extra flair. The jeans are crafted from a dark wash denim fabric with slight color fading and stretch. Complete the look in strappy sandals for a daytime outing or casual dinner!
Fit & Features
- Mid-rise waist
- Wide-leg silhouette
- Cargo-style flap pockets, seam detailing
- Front button and hidden zipper closure
- Seven-pocket styling, belt loop accents
- Dark wash denim, slight color fade and stretch
- Runs true to size
Style Number/Barcode: 06602-0453
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet Demeanor Mock Neck Ribbed Knit Midi Dress
Stay sweet and comfy in this ribbed knit midi dress perfect for any occasion! Designed with cap sleeves, a mock neckline, and a flattering bodycon silhouette, this mid-length dress is trend-worthy with a flirty front slit along the hem. Complete the look with a cute crop jacket and booties!
Fit & Features
- Stretchy ribbed knit fabric
- Mock neckline
- Cap sleeves
- Bodycon fit
- Front slit, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5304
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched Right Essential Crop Top
Elevate your essentials with a flirty new addition. Top features short sleeves and a deep V neck leading to a ruched front. Crop-style silhouette shows off a hint of skin. Top is made from an ultra-soft jersey knit with moderate stretchStyle Number/Barcode: 06002-0088
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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Foxy Lady Slinky Dress
Hey there foxy lady we like your style! This slinky midi dress features a cowl neckline, adjustable spaghetti straps, and a square back with a hidden zipper. The dress slightly cinches at one hip and also offers a sexy side slit. The dress is composed of a smooth satin-like material that offers no stretch yet a relaxed fit. Sexy yet elegant!Style Number/Barcode: 05101-0330
Category Name: 2026 Fall Outfit Trends
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cutie In Floral Smocked Top
Hey babe! Create such a cute look with this adorable ditsy floral smocked top! It features an off the shoulder square neckline, long sleeves with elastic cuffs, a stretchy and smocked bodice, and a cropped hem. The top is composed of a lightweight woven fabric.Style Number/Barcode: 06003-0232
Category Name: 2026 Fall Outfit Trends
Price: $8.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Satin Convertible Crop Top
Amp up your night out 'fits with this sleek satin crop top! It features a sleeveless convertible strap design that gives you the option to wear the straps in a cross-front halter design or a V-neckline. The smooth satin top features a cropped, form-hugging fit. Style with a faux leather mini skirt and clear heels.
Fit & Features
- Sleeveless convertible strap design
- Halter neckline, V-neckline
- Tie-back closure
- Cropped, form-hugging fit
- Satin fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4480
Category Name: 2026 Fall Outfit Trends
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Leather Lace Lug Boots
Lace up in these commanding boots to give your look a bold edge! They feature an around the ankle fit, a lace up front, a round toe, a block heel and a textured lug sole. Boots are composed of a faux leather material.
Style Number/Barcode: 07403-1171
Category Name: 2026 Fall Outfit Trends
Price: $25.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Glam Combat Boots
Lace up and take on the day with plenty of glam! These combat boots feature an around the ankle fit, a lace up front, a round toe and a textured rubber sole. The body features a glittery sheen to add plenty of sparkle to your look! Boots are composed of a glitter mesh material.
Style Number/Barcode: 07403-0033
Category Name: 2026 Fall Outfit Trends
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drama Mama Patent Booties
Bring the drama mama! These patent booties feature a point toe, a medium height block heel. Heel reaches the ankle with a slanted design and has an inner zipper closure. Composed of a shiny patent material.Style Number/Barcode: 07403-0101
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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Turn It Up Lock Faux Leather Purse
Turn your style up a level when you throw in a crossbody satchel! Style over a tee + high waist shorts look for a wowwww factor!
- Square design
- Diamond quilted stitching
- Turn lock closure
- Silver hardware
- Chain + faux leather shoulder / crossbody strap
- Faux leather
- Open inner pocket
Style Number/Barcode: 07203-0319
Category Name: 2026 Fall Outfit Trends
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Waist Tie Front Plaid Skinny Pants
Get a chic office-ready look in these adorable plaid skinny pants! They feature a flattering high rise waist with a V cut out in the front, a tie front detail, and a flattering, tapered fit. Pair these pants with strappy heels and you'll be a major boss babe.
Fit & Features
- High rise waist with front V cut out
- Tie front
- Skinny leg fit
- Allover plaid print
- Woven fabric
Style Number/Barcode: 06402-0264
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Triple Row Rhinestone Ring
Add a hint of sparkle with a ring that is the chic touch you need for your outfit! The ring features a triple row design, open-ended bands, and mini rhinestones. Complete your look with a midi dress and mules.
Fit & Features
- Triple-row design
- Open-ended bands
- Mini rhinestones
Style Number/Barcode: 07004-0099
Category Name: 2026 Fall Outfit Trends
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Viva La Velvet Biker Shorts
Live it up in velvet biker shorts to glam up any outfit! Style with a cute crop top or oversize tee-shirt for a look that's ready to go! The biker shorts feature a high rise waist, a mid-thigh length, and composed of luxe velvet fabric.
Fit & Features
- High rise waist
- Mid-thigh length
- Velvet fabric
- Form hugging fit
Style Number/Barcode: 06503-0184
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Playful Plaid Tie Waist Romper
Keep it playful in a chic plaid romper for your next date night. The romper features a sleeveless V-neckline with spaghetti straps, a chic tie-waist belt, and fitted cheeky shorts. Complete your look with chunky sneakers.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Plaid print
- Tie waist belt
- Cheeky shorts
- Lightweight woven fabric
- Form hugging fit
Style Number/Barcode: 06403-0132
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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Faux Suede Over The Knee Block Heel Boots
Style it up in chic faux suede in these stylish over the knee boots! They feature a flattering pointed toe, sturdy block heel and half faux suede and half elastic knit material for a unique look. Pair these boots with a cute sweater dress for a date night out with bae.
Fit & Features
- Over the knee design
- Pointed toe
- Inner zipper closure
- Block heel
- Half faux suede, half elastic knit material
Style Number/Barcode: 07402-0207
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sleek Faux Leather Ankle Booties
Let these ankle booties complete your sleek and stylish outfit! The ankle booties feature an around the ankle fit, a pointed toe, an inner zipper closure, and a block heel. The booties are composed of a faux leather material. Complete look with a ribbed midi dress.
Fit & Features
- Around the ankle fit
- Pointed toe
- Inner zipper closure
- Block heel
- Faux leather material
Please be advised that these booties run a 1/2 size too small.
Style Number/Barcode: 07403-0461
Category Name: 2026 Fall Outfit Trends
Price: $16.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Save Water Drink Tequila Graphic Crop Tee
Do your part to conserve! This graphic crop tee features short sleeves, a crew neck with a notch cutout, a front script that reads," Save Water/Drink Tequila" and a slashed hem on stretchy cotton fabric. Style with trendy distressed denim shorts for a bar crawl.
Fit & Features
- Short sleeves
- Crew neck, notch cutout
- Front script reads," Save Water/ Drink Tequila"
- Slashed crop hem
- Stretchy cotton fabric
- Runs true to size
Style Number/Barcode: 06002-1681
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Style Snake Print Top
Showcase a cute wild style with this on-trend snake print top. It features long fitted sleeves, a V-neckline with a wrap-front design, and a mid-length hem with drawstrings at each side. Wear this top with your fave pair of denim and clear mules.
Fit & Features
- Long fitted sleeves
- V-neckline, wrap-front design
- Mid-length hem, drawstrings
- Form-hugging fit
- Knit fabric
- Snake print
- Runs true to size
Style Number/Barcode: 06001-3561
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Behavior Cutout Crop Top
Stay on trend with a crop top that creates a major moment! The crop top features an abstract splatter pattern, long sleeves, dual cutouts at the sides, ruched drawstrings, 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 midi skirt.
Shop Matching Midi Skirt: Trendy Behavior High Slit Midi Skirt
Fit & Features
- Abstract splatter pattern
- Long sleeves
- Dual cutouts at the sides
- Ruched drawstrings
- Cropped hem
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06001-3798
Category Name: 2026 Fall Outfit Trends
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Chic High Waist Plaid Flared Pants
Keep your look so chic with plaid pants that are easy to pair with your favorite long sleeve tops! The pants feature a plaid print, a high-rise waist, a tie waist belt, a straight leg, and a flared hem. The pants are composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch.
Fit & Features
- Plaid print
- High rise waist
- Tie-waist belt
- Straight leg
- Flared hem
- Lightweight woven fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06502-0696
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic And Cozy Sherpa Detailed Boots
Get a chic and cozy style this season with these faux suede boots that will totally elevate your look! They feature a below-the-knee design, a subtly pointed toe, a partial inner zipper closure, a faux sherpa trim, and a block heel and lug sole. Style these boots with a sweater dress.
Fit & Features
- Below-the-knee design
- Pointed toe
- Inner zipper closure
- Faux sherpa trim
- Block heel, lug sole
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07402-0742
Category Name: 2026 Fall Outfit Trends
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance