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.

  • Chill Factor Mid-Rise Barrel Denim Jeans

    Low effort, high style—these denim jeans are all about that borrowed-from-the-boys vibe with a modern twist. Comfy, cool, and versatile, they’re the jeans you’ll live in from coffee runs to casual nights out.

    Fit & Features

    • Denim cotton fabric, non-stretch
    • Mid-rise waist
    • Barrel wide-leg silhouette
    • Front button and hidden zipper closure, belt loop accents
    • Front and back pockets
    • Runs true to size

    Style Number/Barcode: 06602-000068

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Lights Bow Grommet Block Heels

    Add some bite to your step—these block heels bring sleek shine with studded straps for just the right amount of edge. Perfect for a night on the town or an event.

    Fit & Features

    • Block heel
    • Square toe
    • Grommet criss cross straps with a bow
    • Closed ankle with adjustable strap and buckle closure
    • Luxe fit cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000347

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strut Ready Sling-Back Stiletto Pumps

    The sling-back stiletto heels that instantly make every outfit hotter. Sleek, minimal, and endlessly wearable, they’re the pair you’ll reach for on repeat for day or night looks.

    Fit & Features

    • 3.5" Stiletto heel
    • Open square toe
    • Toe strap, cutout side design
    • Sling-back ankle strap
    • Faux nubuck material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000342

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Luxe Faux Suede Trench Jacket

    Your fall staple, sorted. This faux suede trench jacket nails cozy-chic with its belted waist and tailored finish—perfect for crisp days, strolling downtown, and everything in between!

    Fit & Features

    • Smooth faux suede fabric
    • Long sleeves with button cuffs
    • Collared neckline, front pockets
    • Button-down front closures
    • Belted tie-waist
    • Tailored short-length silhouette
    • Runs true to size

    Style Number/Barcode: 06204-000036

    Category Name: 2026 Fall Outfit Trends

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ring It In Grommet Wide-Leg Denim Jeans

    Jeans with a little extra edge—literally. The grommet detailing down the sides takes this wide-leg fit from everyday basic to bold statement, perfect for any plans!

    Fit & Features

    • Denim fabric
    • Mid-rise waist
    • Wide-leg fit with grommet side embellishments
    • Front button closure, pockets, belt loops
    • Runs true to size

    Style Number/Barcode: 06602-000067

    Category Name: 2026 Fall Outfit Trends

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strings Attached Lace-Up Denim Skort

    This isn’t your regular denim skort. Designed with lace-up sides and raw edge details, it’s equal parts effortless and unapologetic. Wear it when you want your outfit to do the talking.

    Fit & Features

    • Denim fabric
    • High-rise waist
    • Front zip-up closure
    • Lace-up sides
    • Bodycon silhouette
    • Mini-length skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06603-000094

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Edge Wide Calf Platform Boots

    From coffee runs to night out plans, these knee-high boots deliver instant cool. The chunky heel and streamlined design make them an everyday essential.

    Fit & Features

    • 3” block heel, 8” leg opening, 14.5” shaft
    • Square toe
    • Side zipper closure
    • Knee-high length
    • Wide calf design
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000128

    Category Name: 2026 Fall Outfit Trends

    Price: $48.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: 7, 10

    Product Badge:
    • Best Seller
  • Throwback Cool Pleated Denim Mini Skort

    Y2K vibes on lock—this pleated denim mini skort is made for low-rise moments and weekend plans. Pair it with crop tops, corsets, or oversized knits for that effortless it-girl edge.

    Fit & Features

    • Dark wash denim fabric, stretchy knit shorts lining
    • Low-rise waist, belt loop accents
    • Side zipper and hook-eye closure
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 06603-000090

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Flare Mid-Rise Flare Denim Jeans

    These flare jeans serve up vintage vibes with bold patch pockets and a sleek, leg-lengthening fit. Dress them down with sneakers or pair with heels for that effortless off-duty model look.

    Fit & Features

    • Medium wash vintage-inspired denim fabric
    • Mid-rise waist
    • Hip-hugging fit
    • Flared hem
    • Front and back pockets, front button and hidden zipper closure
    • Belt loop accents
    • Runs true to size

    Style Number/Barcode: 06602-000065

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffle With It Denim Mini Skort

    Flirty meets edgy—this ruffled denim skort brings major attitude with a playful twist. Pair it with boots, sneakers, or heels and let your legs do the talking.

    Fit & Features

    • Denim fabric with contrast stitching
    • Mid-rise belted waist
    • Tiered ruffle layered design
    • Mini length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06603-000088

    Category Name: 2026 Fall Outfit Trends

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Falling For Denim Mini Skirt

    The mini that does it all—this denim skirt is your fall styling MVP. Pair it with mules and a cute top for that effortless street-style vibe or with tights and boots for casual night outs.

    Fit & Features

    • Dark wash denim fabric
    • Mid-rise waist
    • Form-hugging fit
    • Mini-length hem
    • Extended dual button closure strap
    • Four-pocket styling, belt loops
    • Runs true to size

    Style Number/Barcode: 06601-000014

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can't Blend In Mid-Rise Camouflage Denim Skort

    This one’s giving combat cutie. With built-in shorts and a statement belt, this camo denim skort is ready for concerts or weekend fun.

    Fit & Features

    • Camouflage print, denim cotton fabric, stretchy knit shorts lining
    • Mid-rise belted waist
    • Front flap pockets, 93' embroidered patch detail
    • Form-hugging fit, frayed mini-length hem
    • Front button and hidden zipper closure, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000089

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Sleek Faux Suede Trench Coat

    Crisp air, cozy layers, city chic. This longline trench coat is your fall go-to—perfect over knits, minis, or denim for coffee runs, office days, and golden hour strolls through the city.

    Fit & Features

    • Smooth faux suede fabric, woven lining
    • Lapel collar neckline
    • Long sleeves
    • Open front design, single button closure
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06204-000035

    Category Name: 2026 Fall Outfit Trends

    Price: $14.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Factor Faux Suede Moto Jacket

    Instantly level up any 'fit—this moto jacket brings all the effortless edge. With its oversized silhouette and luxe faux suede, it’s your grab-and-go layer for nights out or laid-back hangs.

    Fit & Features

    • Faux suede fabric
    • Lapel collar, studded details
    • Long sleeves, studded shoulder straps
    • Zip-front design, zippered accents
    • Belted waist
    • Mid-length hem
    • Oversized fit

    Style Number/Barcode: 06204-000034

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Chaos Mid-Rise Wide Leg Denim Jeans

    These distressed wide leg jeans bring a laidback attitude with ripped details and a relaxed fit. Perfect for pairing with baby tees, oversized blazers, or a little crop moment.

    Fit & Features

    • Medium denim fabric
    • Mid-rise waist
    • Distressed back accents
    • Wide-leg fit
    • Front button closures, belt loop accents
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06602-000064

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cropped Attitude Faux Leather Jacket

    From coffee runs to late nights, this faux leather jacket nails that effortless cool-girl vibe in the city!

    Fit & Features

    • Faux leather fabric, sewn-in woven lining
    • Long sleeves
    • Collar neckline
    • Front zip-up closure
    • Front pockets
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06204-000033

    Category Name: 2026 Fall Outfit Trends

    Price: $49.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S

  • Retro Rise Knee High Platform Boots

    A little vintage, a little modern—these knee-high boots are the ultimate outfit maker. With a smooth faux leather finish, a sturdy block heel, and a platform sole perfect for elevating any outfit.

    Fit & Features

    • Block heel
    • Square toe
    • Side zipper closure
    • Knee-high shaft
    • Side zipper closure
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000043

    Category Name: 2026 Fall Outfit Trends

    Price: $48.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Factor Faux Leather Bomber Jacket

    Instantly upgrade your street style with this faux leather bomber that’s cropped, collared, and cinched in all the right places. It’s that throw-on-and-look-hot kind of layer your closet’s been waiting for.

    Fit & Features

    • Vintage-inspired faux leather fabric, sewn-in woven lining
    • Long sleeves
    • Collared neckline
    • Front zip-up closure
    • Front pockets
    • Elasticized cinch crop hem
    • Runs true to size

    Style Number/Barcode: 06204-000032

    Category Name: 2026 Fall Outfit Trends

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L, XL

  • Talk Glossy to Me Patent Shoulder Bag

    This patent shoulder bag brings that pop of color every outfit’s been begging for—perfect for any occasion and everyday styling!

    Fit & Features

    • Shoulder strap
    • Front flap closure
    • Spacious interior
    • Glossy patent faux leather material

    Style Number/Barcode: 07203-000151

    Category Name: 2026 Fall Outfit Trends

    Price: $25.90

    Availability: In Stock

    Available Color: BROWN, WHITE

    Available Size: NS

  • City Strolls New York Denim Jeans

    Serving laidback cool with a side of street cred—these jeans bring the vibe. The relaxed, wide leg fit and bold New York embroidery at the back that makes heads turn.

    Fit & Features

    • Medium wash denim fabric
    • Mid-rise waist
    • Embroidered "New York" across the back
    • Wide-leg fit
    • Front button closure, belt loops
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06602-000061

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coast to Curb Los Angeles Denim Jeans

    Big city energy meets laidback vibes—these jeans will be your favorite for grabbing matcha or any casual plans. The wide leg fit and bold Los Angeles embroidery make every sidewalk your runway.

    Fit & Features

    • Medium denim fabric
    • Mid-rise waist
    • Wide leg silhouette
    • Back pockets with "Los Angeles" embroidered lettering
    • Runs true to size

    Style Number/Barcode: 06602-000060

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Steppin Up Block Heel Knee High Boots

    Big boot energy only—these tall babes instantly elevate any 'fit. A sleek silhouette with a comfy block heel makes them perfect for day-to-night flexing.

    Fit & Features

    • 3" Stacked block heel, 8" leg opening, 12" shaft height
    • Platform sole
    • Round toe
    • Complete inner zipper closure
    • Knee-length shaft
    • Faux leather material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07402-000044

    Category Name: 2026 Fall Outfit Trends

    Price: $48.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 8, 8.5, 9, 10

    Product Badge:
    • Best Seller
  • Double Take Mesh Sling-Back Pumps

    A little sheer, a little sassy—these pumps were made for double takes. The kitten heel keeps it comfy while the sling-back strap serves all-day, all-night vibes.

    Fit & Features

    • 2" Kitten stiletto heel
    • Closed pointed toe
    • Sheer mesh material
    • Adjustable sling-back strap, buckle detail
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000337

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild West Glow Lace Up Mini Dress

    Giving rodeo-ready meets it-girl chic. The faux suede finish and lace-up front serve sultry vibes that work from concerts to bachelorette trips to the country!

    Fit & Features

    • Micro faux suede fabric
    • Halter V-neckline
    • Front lace-up bust design
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000313

    Category Name: 2026 Fall Outfit Trends

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale