2026 Fall Outfit Trends

STYLE SPOTLIGHT

Women's Denim Bottoms

Fall Sweaters & Cardigans

Women's Jackets

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.

  • High Rise Edgy Distressed Skinny Jeans

    Take on an edgy feel with these distressed jeans that don't play it safe! The jeans feature a high-rise waist, distressed accents throughout, and a super skinny leg fit. Complete look with a tie-front top. 

    Fit & Features

    • High rise waist 
    • Front button and hidden zipper closure
    • Five-pocket and belt loop design
    • Distressed accents throughout
    • Super skinny leg fit
    • Medium-wash denim fabric
    • Moderate stretch, fits true to size

    Style Number/Barcode: 06602-0165

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fab and Frayed Distressed Skinny Jeans

    Keep it fab in jeans that bring the drama! These must-have skinny jeans feature a mid-rise fit, heavy destruction throughout and a skinny leg fit. Complete look with a basic bodysuit to let the destruction speak for itself. 

    Fit & Features

    • Mid-rise fit
    • Single-button and zipper closure
    • Traditional five-pocket and belt loop design 
    • Heavy destruction throughout 
    • Skinny leg fit
    • Medium wash denim fabric 

    Style Number/Barcode: 06602-0164

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Rise Destructed Boyfriend Jeans

    Take on the day in destructed jeans that bring the edge. The jeans feature a high rise waist, moderate destruction on the left leg, and a boyfriend fit with a cropped hem. Complete your look with a long sleeve ribbed top. 

    Fit & Features

    • High rise waist
    • Single-button and zipper closure
    • Moderate destruction on the left leg
    • Boyfriend fit 
    • Cropped hem
    • Black denim fabric  

    Style Number/Barcode: 06602-0176

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On the Edge High Rise Destructed Boyfriend Jeans

    Bring the edge in these jeans to show off your edgy side! The jeans feature a high rise waist, heavy destruction throughout, and a boyfriend fit with a cropped hem. Complete look with a flannel top to channel those fall vibes. 

    Fit & Features

    • High rise waist
    • Single-button and zipper closure
    • Traditional five-pocket and belt loop design 
    • Heavy destruction throughout 
    • Boyfriend fit with a cropped hem
    • Black denim wash fabric 

    Style Number/Barcode: 06602-0178

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Twist of Plaid Romper

    Give your look a trendy twist in a plaid romper! The romper features a sleeveless sweetheart neckline, sleek spaghetti straps, a trendy twist-front accent at the center of the bodice, and a plaid print. The romper is composed of a lightweight woven fabric that offers a form hugging fit. Complete look with chunky sneakers for a casual feel. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Sleek spaghetti straps
    • Twist-front accent at the center of the bodice
    • Plaid print
    • Wide-leg shorts with a skirt overlay

    Style Number/Barcode: 06503-0161

    Category Name: 2026 Fall Outfit Trends

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mid Rise Destructed Skinny Jeans

    Keep it sleek in basic skinny jeans for your next coffee date. The jeans feature a mid-rise fit, a sleek skinny leg fit, and heavy destruction throughout. Complete look with a scoop neck bodysuit. 

    Fit & Features

    • Mid-rise fit
    • Single-button and zipper closure
    • Traditional five-pocket and belt loop design
    • Skinny leg fit
    • Heavy destructed detailing
    • Light-medium wash denim fabric  

    Style Number/Barcode: 06602-0171

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Sophistication Crepe Trench Coat

    Keep it so sophisticated in a trench coat that is perfect for creating chic workwear outfits. The trench coat features a traditional lapel collar, quarter-length sleeves, a draped open front, and an above the knee fit. The trench coat is composed of a crepe knit fabric that offers a relaxed fit. Complete look with clear mules.

    Fit & Features

    • Lapel collar
    • Ruched 3/4 length sleeves
    • Draped open front 
    • Above the knee length
    • Crepe knit fabric

    Style Number/Barcode: 06204-0727

    Category Name: 2026 Fall Outfit Trends

    Price: $13.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • French Terry Knit Shorts

    Keep it sporty and chic in these trendy french terry knit shorts! They feature a high rise banded waist with a mid-thigh length, relaxed and comfortable fit. Pair these shorts with a basic cropped cami and chunky sneaks for a look you can take from lounging to hanging with the squad.

    Fit & Features

    • High rise banded waist
    • Slanted front pockets
    • Mid-thigh length relaxed fit
    • French terry knit fabric

    Style Number/Barcode: 06503-0198

    Category Name: 2026 Fall Outfit Trends

    Price: $11.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Vibes Lug Sole Block Heel Booties

    Get major edgy vibes in these stylish booties! They feature an ankle-high design with a gore detail, a trendy lug sole, and a sturdy block heel. Pair these booties with your fave pair of dark wash skinny jeans.

    Fit & Features

    • Ankle-high design
    • Almond toe
    • Gore detail
    • Lug sole
    • Block heel
    • Faux microsuede material

    Style Number/Barcode: 07403-0531

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Fab Faux Suede Block Heel Booties

    Fall back on fab basics that complete your textured layered outfits. The booties feature an around the ankle fit, an almond toe, and a block heel. Complete the look with a cardigan and joggers for those low-key vibes. 

    Fit & Features

    • Around the ankle fit
    • Almond toe
    • Inner zipper closure
    • Block heel 
    • Faux suede material 


    Please be advised that these booties run 1/2 a size small.

    Style Number/Barcode: 07403-0533

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Right Knit Block Heel Booties

    These booties are the knit piece that you need for your layered outfit! The booties feature an around the ankle fit, an almond toe, a knit material body, and a short block heel. Complete look with a bodysuit and jeans. 

    Fit & Features

    • Around the ankle fit
    • Almond toe
    • Knit material body
    • Short block heel

    Style Number/Barcode: 07403-0538

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Top It Off Faux Wool Cabby Hat

    Top off your fabulous 'fit with this chic cabby hat! It features a traditional cabby design with a faux leather brim and braided trims with button accents. Pair this hat with a trendy crop top and denim for a casual slay you can wear everyday.

    Fit & Features

    • Traditional cabby design
    • PU brim
    • Braided trims with button accents
    • Faux wool material

    Style Number/Barcode: 07302-0278

    Category Name: 2026 Fall Outfit Trends

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Stunner Crepe Knit Crop Top

    Be a total stylish stunner in this chic crepe knit crop top! Featuring a high neckline, a cropped tulip hem and a form-hugging fit, this top would pair perfectly with high waist denim and heeled booties. Make this part of your new fall wardobe!

    Fit & Features

    • High neckline
    • Long fitted sleeves
    • Cropped tulip hem
    • Form-fitting style
    • Crepe knit fabric
    • Moderate stretch

    Style Number/Barcode: 06001-2778

    Category Name: 2026 Fall Outfit Trends

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Stunner Snake Print Crop Top

    You'll be a trendy stunner in this off the shoulder crop top! It features a sweetheart neckline with a ruffle trim, long sleeves with cinched hems, hook and eye front closures, a cropped, form-hugging fit, and an all-over snake print. Pair this top with mom jeans and booties for a stylish look.

    Fit & Features

    • Off the shoulder sweetheart neckline
    • Ruffle trim
    • Long sleeves with cinched hems
    • Hook and eye front closures
    • Cropped, form-fitting style
    • Snake print
    • Woven fabric

    Style Number/Barcode: 06003-1137

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plaid Perfection Ruched Mini Skirt

    Keep it preppy in a plaid skirt that is totally on-point, girl! The skirt features a high rise waist, ruched side seams, and a plaid print. The skirt is composed of a lightweight woven fabric that offers a form hugging fit with a moderate stretch. Complete look with a tube top.

    Fit & Features

    • High rise waist
    • Plaid print
    • Ruched side seams
    • Lightweight woven fabric
    • Form hugging fit
    • Moderate stretch

    Style Number/Barcode: 06501-0335

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Cutie Oversized Button-Up Tunic

    You'll be a total classic cutie in this chic oversized tunic! It features a complete button-down front and an adjustable back strap, giving you the option to style it with the collar or give it an off the shoulder look. Pair this top with light wash denim and heeled mules for an effortless everyday vibe.

    Fit & Features

    • Collared neckline
    • Long sleeves with dual buttons to cuff
    • Complete button-down front
    • Adjustable back strap with double D ring detailing
    • Oversized fit
    • Woven fabric with no stretch

    Style Number/Barcode: 06003-1136

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Faux Leather Suspender Mini Skirt

    A suspender skirt is all you need for a classically chic outfit! Perfect for creating a fab back to school outfit, layer with your favorite long sleeve ribbed top and ankle booties. The suspender skirt features a scoop neckline, spaghetti tie straps, and a mini length silhouette. 

    Fit & Features 

    • Sleeveless scoop neckline
    • Spaghetti tie-straps
    • Mini length silhouette
    • Faux leather fabric
    • Form hugging fit 

    Style Number/Barcode: 06401-0292

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High-Rise Destructed Boyfriend Jeans

    Give your casually chic outfits an edgy aesthetic with these deconstructed high-rise jeans. These boyfriend-fit medium-wash denim jeans have the perfect amount of ripped detailing at the knees with a straight-leg silhouette for an absolutely on-trend look. Pair these high-waist ripped jeans with a cute crop top and chunky sneakers for day or a sparkly bustier with strappy heels for a sexy night look.

    Fit & Features

    • High-rise waist
    • Boyfriend style leg
    • Distressed detailing, slits at the knees
    • Multi button-down front closure
    • Five-pocket and belt loop design
    • Medium wash denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0184

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Totally Basic Vibes Ribbed Crop Top

    Rock basic vibes in a crop top that is part cute and part casual. The crop top features a mock neckline, long sleeves, and a ladder back detail. The top is composed of a ribbed knit fabric that offers a form hugging fit with slight stretch. Complete look with high waist joggers.

    Fit & Features

    • Mock neck
    • Long sleeves
    • Ladderback design 
    • Cropped hem 
    • Ribbed knit fabric
    • Form hugging fit
    • Slight stretch 

    Style Number/Barcode: 06001-2969

    Category Name: 2026 Fall Outfit Trends

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Houndstooth Pleated Mini Skirt

    Get a flirty vibe pairing this chic mini skirt with heeled booties! The skirt features a high rise waist, a mini length flared silhouette, pleated detailing, and a trendy houndstooth print. Wear this skirt to a holiday party for a stylish 'fit!

    Fit & Features

    • High rise elastic banded waist
    • Mini length flared silhouette
    • Knit fabric with plenty of stretch
    • Houndstooth print

    Style Number/Barcode: 06501-0333

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Next Level High Rise Skinny Jeans

    Elevate your looks with skinny jeans that keep your outfits on point! These must-have jeans feature a high rise fit, light destructed detailing with knee slits, and a skinny leg fit with a cropped hem. Complete look with a ribbed crop top.

    Fit & Features

    • High rise waist
    • Single-button with zipper closure
    • Traditional five-pocket with belt-loop design
    • Light destructed detailing with knee slits
    • Skinny leg fit with slightly cropped hem
    • Medium wash fabric
    • Form hugging fit

    Style Number/Barcode: 06602-0189

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Good Faux Suede Block Heel Booties

    These booties bring major feel good vibes to your layered outfits! The booties feature an around the ankle fit, a back zipper closure, a pointed toe, and a low block heel. Complete look with a ribbed midi dress and moto jacket.

    Fit & Features

    • Around the ankle fit
    • Back zipper closure
    • Pointed toe
    • Low block heel
    • Faux suede material

    Style Number/Barcode: 07403-0526

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Scorpio Babe Graphic Tee Shirt

    Show off your sign in a tee that says it all! The graphic tee features lettering that reads: "Strong, Seductive, Savage" with "Scorpio" lettering at the center of the bodice. The tee is composed of a jersey knit fabric that offers a relaxed fit with a moderate stretch. Complete look with a high rise mini skirt. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • "Strong, Seductive, Savage" lettering 
    • "Scorpio" lettering
    • Jersey knit fabric
    • Relaxed fit, moderate stretch

    Style Number/Barcode: 06002-0661

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Classic Plaid Mini Skirt

    Keep it classy in a plaid skirt this season! The skirt features a high rise waist, a plaid print, and, a mini side slit. Complete look with a long sleeve black top and thigh high boots.

    Fit & Features

    • High rise waist
    • Plaid print
    • Mini side slit
    • Brushed woven fabric 
    • Form hugging fit
    • Minimal stretch 

    Style Number/Barcode: 06401-0281

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free