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.

  • Cool Girl Oversized Denim Jacket

    Effortlessly cool in an oversized fit, this denim jacket offers laidback vibes perfect for any day or night plans.

    Fit & Features

    • Light wash cotton-blend denim fabric
    • Long sleeves, button cuffs
    • Collar neckline
    • Hidden front snap-button closures
    • Front flap pockets with snap-button closures
    • Oversized fit

    Style Number/Barcode: 06203-000013

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Utility Chic Mid-Rise Cargo Denim Jeans

    Built for errands and entrance-making. These mid-rise cargo denim jeans serve laidback cool with workwear details and a fit that still knows how to flex with your favorite tops.

    Fit & Features

    • Dark wash cotton-blend denim fabric
    • Mid-rise waist
    • Straight-leg fit
    • Front and back cargo flap pockets
    • Front button and hidden zipper closure
    • Belt loop accents, three-pocket styling
    • Runs true to size

    Style Number/Barcode: 06602-000035

    Category Name: 2026 Fall Outfit Trends

    Price: $49.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: XS, S, M, L, XL

  • Throwback Cool Denim Cargo Mini Skirt

    Low-rise nostalgia meets modern street style—this denim cargo mini skirt is made for layering with baby tees, tanks, or oversized fits. The pocket detail gives it that effortless “just stepped out of an early 2000s music video” energy.

    Fit & Features

    • Denim fabric with color fade effect
    • Mid-rise waist
    • Cargo-style front and side pockets
    • Fitted mini-length hem
    • Front button closure, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000062

    Category Name: 2026 Fall Outfit Trends

    Price: $39.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M, L, XL

  • On The Go Faux Leather Hobo Shoulder Bag

    Casual, cool, and made to carry it all—this hobo bag gets you. Toss it over your shoulder and take on the day with effortless style.

    Fit & Features

    • Top shoulder strap
    • Slouchy hobo silhouette
    • Top zipper closure
    • Spacious lined interior
    • Faux leather material

    Style Number/Barcode: 07203-000035

    Category Name: 2026 Fall Outfit Trends

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Prepped For Style Pleated Plaid Skort

    This plaid pleated mini skort is flirty, playful, and perfect for styling with baby tees or oversized layered this fall season!

    Fit & Features

    • Plaid print, woven fabric, shorts lining
    • Low-rise waist
    • Pleated mini-length skirt overlay
    • Runs true to size

    Style Number/Barcode: 06403-000041

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Cue Crop Denim Bomber Jacket

    Off-duty but still on. This cropped denim bomber jacket adds instant cool style to anything you throw it over—because basics deserve better.

    Fit & Features

    • Cotton denim fabric, no stretch
    • Standing collar neckline
    • Front hidden zip-up closure, snap-button closures
    • Front flap pockets
    • Elasticized cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06204-000030

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plaid Attitude Pleated Mini Skort

    Prep, but make it playful. This plaid pleated mini skort features a buckle belt detail that gives school-girl energy with a cool-girl twist. Perfect for pairing with the matching cropped vest.

    Shop Matching Top: Plaid Attitude Cropped Vest Top

    Fit & Features

    • Plaid woven fabric
    • Mid-rise waist with belt detail
    • Pleated mini-length skirt overlay
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000040

    Category Name: 2026 Fall Outfit Trends

    Price: $15.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Speed Dial Faux Leather Motocross Jacket

    Giving moto muse in the chicest way—this faux leather jacket was made to own the scene. The cropped fit and mixed textures add instant edge, whether you’re layering over a tank or styling with your favorite mini dress.

    Fit & Features

    • Washed faux leather fabric
    • Ribbed knit fabric on the front and down the sleeves
    • High neck, button closure
    • Zippered pockets, zip-front design
    • Long sleeves
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000028

    Category Name: 2026 Fall Outfit Trends

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L, XL

  • Throttle Babe Faux Leather Moto Vest

    Bold girl vibes with a zip-up twist. Rev the engine to your cool style in this faux leather moto vest designed with a vintage-inspired look and a cropped length that flaunts your edgy allure!

    Fit & Features

    • Vintage-inspired faux leather fabric, sewn-in knit lining
    • Standing collar neckline with snap-button closure
    • Front zip-up closure
    • Faux chest zippered pockets, functional side zipper pockets
    • Cropped length hem
    • Runs true to size

    Style Number/Barcode: 06204-000029

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Star Cheetah Mid-Rise Denim Jeans

    These flare denim jeans feature leopard star patches on the back for that unexpected pop of sass, perfect for lunch meetups, concert nights, or just showing off your wild streak.

    Fit & Features

    • Denim fabric, slight stretch
    • Mid-rise waist
    • Hip-hugging fit, flared leg silhouette
    • Cheetah star print patch detailing at back
    • Front button and hidden zipper closure
    • Two front pockets, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06602-000030

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring The Attitude Lace-Up Bomber Jacket

    Vintage vibes, side lace-ups, and a trendy silhouette. This jacket is perfect for layering over a slip dress or denim with attitude!

    Fit & Features

    • Vintage-inspired faux leather fabric, sewn-in woven lining
    • Long sleeves, snap-button cuffs
    • Collar neckline
    • Front zip-up closure
    • Two front pockets
    • Side lace-up plackets
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06204-000026

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Lines Sheer Pattern Fishnet Tights

    These sheer patterned tights add instant sultriness to dresses, skirts, or oversized layers. A bold yet wearable staple that turns even the simplest fit into a statement.

    Fit & Features

    • Sheer fishnet fabric
    • Allover chainlink-inspired pattern
    • Elastic high-rise waistband
    • Soft and comfortable

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07306-000010

    Category Name: 2026 Fall Outfit Trends

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prep School Crush Plaid Mini Skort

    Plaid but make it flirty—this pleated mini skort has side bow ties and a preppy vibe that’s giving major cool-girl energy. Perfect with tees and chunky knits or crop tops and heels for a cute evening look.

    Fit & Features

    • Mid-rise waist
    • Side bow accents
    • Pleated mini skirt overlay
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000035

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trailblazer Faux Suede Fringe Jacket

    Western flair meets cool-girl edge—this cropped suede jacket is all about the drama in motion. Layer it over your outfit for concerts, country nights, or whenever you want some cowgirl flair.

    Fit & Features

    • Soft, smooth faux suede fabric
    • Long sleeves
    • Collared neckline
    • Fringe trim throughout
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06204-000022

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Stance Faux Leather Stiletto Boots

    Cold-weather dressing just got elevated. These faux leather boots bring timeless polish with a pointed toe and sleek under-the-knee cut, with a stiletto heel that pairs effortlessly with fall layers.

    Fit & Features

    • 3” stiletto heel, 7.5” leg opening, 15” shaft
    • Pointed-toe
    • Side zipper closure
    • Under-the-knee length
    • Sleek faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000010

    Category Name: 2026 Fall Outfit Trends

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • Best Seller
  • Kiss the Spotlight Halter Romper

    Flirty, flowy, and low-key iconic. This romper’s deep neckline and twirl-worthy shorts bring main feed energy to your night-out lineup.

    Fit & Features

    • Slinky knit stretchy fabric
    • Halter plunge neckline, tie straps
    • Open back
    • Flowy shorts hem
    • Runs true to size

    Style Number/Barcode: 06503-000079

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alluring Bloom Flocked Floral Mesh Maxi Dress

    This dress is giving sultry garden goddess. The strapless neckline and body-hugging mesh silhouette keep it sleek, while the flocked floral detail adds just the right amount of romance. Perfect for whenever you want to turn a subtle moment into the moment.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Flocked floral print pattern
    • Strapless straight-across neckline
    • Back zipper closure
    • Ruching
    • Fitted silhouette, midi-length flared hem
    • Runs true to size

    Style Number/Barcode: 05101-000180

    Category Name: 2026 Fall Outfit Trends

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Flair Lace Ruffle Mini Dress

    This lace mini dress brings flirty movement with tiered ruffles and a fitted bodice—ideal for concerts, brunch, or anywhere the vibe is playful yet chic.

    Fit & Features

    • Sheer lace fabric with knit lining, high stretch
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Fitted bodice, ruching
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000179

    Category Name: 2026 Fall Outfit Trends

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Chic To Quit Sling-Back Pumps

    She’s giving vintage chic with a modern twist. These patent faux leather sling-back pumps are all about that buckle detail, block heel, and padded insole comfort you’ll want from day to night.

    Fit & Features

    • Block heel
    • Patent faux leather material
    • Closed pointed toe
    • Thin adjustable strap across the foot, buckle detail
    • Thin adjustable sling-back strap, buckle detail
    • Padded insole
    • Runs true to size

    Style Number/Barcode: 07401-000198

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gloss And Bow Block Heel Loafers

    Classic meets playful—these patent loafers get a girly twist with satin bows and chunky block heels that keep them modern.

    Fit & Features

    • Block heel
    • Square toe
    • Satin bow accent
    • Loafer silhouette
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07405-000001

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet and Sleek Halter Crop Top

    Flirty fit, effortless feel. This halter crop top hugs in all the right places with a square neckline that’s cute for brunch and weekend fun.

    Fit & Features

    • Woven fabric, slight stretch
    • Square halter neckline, elasticized strap
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000094

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Luxe Minimalist Toe Ring Strappy Stiletto Heels

    These strappy stiletto heels were built for chic nights out. With sleek straps and a gold hardware toe ring accent, they’re the perfect balance of classy and cool for weeknight dinners to weekend RSVP's.

    Fit & Features

    • Stiletto heel
    • Square toe with hardware toe ring accent
    • Strappy design
    • Adjustable ankle strap, buckle closure
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000166

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute But Casual Bow Knit Bolero

    Perfect for those “is it chilly or am I just cute” moments. This bolero is designed with adorable bow trims, cozy long sleeves, and an ultra-cropped hem that flaunts your outfit!

    Fit & Features

    • Soft rib knit stretchy fabric
    • Long sleeves
    • Open front design
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000074

    Category Name: 2026 Fall Outfit Trends

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Stride Suede Leopard Sneakers

    Step into your fierce era. These leopard micro suede side stripe sneakers blend bold vibes with everyday comfort—perfect for casual hangs or making errands a little extra.

    Fit & Features

    • Round toe
    • Low-top silhouette
    • Side stripe faux leather accent
    • Lace-up closure
    • Cushioned insole, rubber sole
    • Micro faux suede material, leopard print
    • Runs true to size

    Style Number/Barcode: 07407-000001

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free