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.

  • Wild Side Leopard LA Baseball Cap

    West Coast but make it wild. This leopard suede LA embroidered baseball cap is the statement topper your casual ‘fit has been waiting for.

    Fit & Features

    • Classic baseball cap silhouette
    • Soft micro suede finish with leopard print
    • LA embroidered detail on the front
    • Adjustable back strap for a custom fit

    Style Number/Barcode: 07302-000197

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Low Key Cool LA Baseball Cap

    Repping the city never looked this effortless. This LA embroidered baseball cap is the laid-back staple you’ll throw on with everything from streetwear fits to off-duty looks.

    Fit & Features

    • Classic baseball cap silhouette
    • Structured curved brim
    • LA embroidered detail on front
    • Adjustable back strap for a custom fit

    Style Number/Barcode: 07302-000195

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • City Girl New York Baseball Cap

    For the girl who’s always in a New York state of mind. This embroidered baseball cap is the casual-cool essential that goes with literally everything.

    Fit & Features

    • Classic baseball cap silhouette
    • Structured curved brim
    • New York embroidered detail
    • Adjustable back strap for a custom fit

    Style Number/Barcode: 07302-000193

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Aura Long Sleeve Midi Dress

    Minimal effort, maximum effect. This off-the-shoulder ribbed midi dress hugs in all the right places with a soft stretch knit that’s made for cozy-chic moments. Style it with gold hoops and strappy heels for that quiet luxury vibe.

    Fit & Features

    • Soft rib knit fabric, sewn-in knit lining, moderate stretch
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Center back slit
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000331

    Category Name: 2026 Fall Outfit Trends

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • West Coast Vibes LA Corduroy Baseball Cap

    Easy, breezy, and so LA. This corduroy embroidered baseball cap adds laid-back cool to any ‘fit—perfect for coffee runs, casual hangs, or weekend adventures.

    Fit & Features

    • Classic baseball cap silhouette
    • LA embroidered detail on front
    • Adjustable back strap for a custom fit
    • Soft corduroy material

    Style Number/Barcode: 07302-000192

    Category Name: 2026 Fall Outfit Trends

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serve Confidence Striped Woven Collared Top

    This striped woven collared top serves confidence with a deep V and flyaway front where clean lines meet a little bit of bold—perfect for denim nights, layered days, or styled up for when subtle just isn’t the vibe.

    Fit & Features

    • Sleek striped woven fabric, no stretch
    • Collared neckline
    • Deep V-front opening
    • Double bar strap detail, flyaway front design
    • Long sleeves with flared hems
    • Mid-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-000215

    Category Name: 2026 Fall Outfit Trends

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Chic Attitude Ribbed Knit Off-The-Shoulder Midi Dress

    A sleek off-the-shoulder midi dress with just the right dose of attitude. The ribbed knit snatches softly, the cutout adds that chic twist, and the midi length keeps the whole look effortlessly elevated.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Off-the-shoulder sweetheart neckline, no-slip strip, center hardware accent
    • Keyhole cutout below the bust
    • Long fitted sleeves
    • High-cut front slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000222

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • LA Vibes Corduroy Baseball Cap

    Rep the city in cozy-cool style—this two-tone corduroy baseball cap brings a laidback fall twist to your streetwear fits. Perfect for coffee runs, stadium days, or just topping off your ‘fit with West Coast flair.

    Fit & Features

    • Curved brim with contrast panel design
    • Classic baseball cap silhouette
    • Embroidered Los Angeles front detail
    • Adjustable back strap

    Style Number/Barcode: 07302-000191

    Category Name: 2026 Fall Outfit Trends

    Price: $3.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Stroll Corduroy Baseball Cap

    Laidback but make it luxe—this corduroy baseball cap brings cozy texture and fall-girl vibes to your off-duty fits, perfect for pumpkin patches, PSL runs, and downtown strolls.

    Fit & Features

    • Wide curved brim
    • Classic baseball cap silhouette
    • Adjustable back strap
    • Corduroy material

    Style Number/Barcode: 07302-000190

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Code Faux Leather Cargo Pants

    Utility, but make it chic. These faux leather cargo pants bring a bold edge with a high-rise fit and wide-leg silhouette that’s all confidence, no effort. They’re the kind of pants that turn errands into an outfit moment.

    Fit & Features

    • Sleek faux leather fabric, slight stretch
    • High-rise waist, elasticized trim insert
    • Wide-leg silhouette
    • Cargo side pockets, hip side pockets
    • Front button and hidden zipper closure
    • Belt loop accents
    • Runs true to size

    Style Number/Barcode: 06402-000015

    Category Name: 2026 Fall Outfit Trends

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L, XL

  • Wrapped Up Cute Denim Pleated Skort

    Flirty meets functional—this denim skort has a wrap front with side tie detail and playful pleats for that perfect mix of cute and casual. 

    Fit & Features

    • Dark wash denim
    • Mid-rise waist
    • Back zipper and hook-eye closure
    • Wrap side tie design
    • Pleated mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06603-000122

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Carry All Day Faux Suede Shoulder Bag

    Low-key luxe vibes—this faux suede shoulder bag is giving effortless polish. Compact but chic, it’s the go-to accessory for coffee runs, date nights, and everything in between.

    Fit & Features

    • Faux suede material
    • Small rectangular shape
    • Adjustable shoulder strap with buckle detail

    Style Number/Barcode: 07203-000125

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out And About Faux Suede Tote Bag

    Soft, slouchy, and seriously chic—this faux suede hobo bag nails the off-duty vibe. The roomy interior and matching zip pouch make it perfect for tossing in your essentials and heading anywhere from coffee runs to weekend plans.

    Fit & Features

    • Top shoulder strap
    • Slouchy hobo silhouette
    • Top snap-button closure
    • Spacious interior
    • Includes a zippered pouch to hold essentials
    • Soft faux suede material

    Style Number/Barcode: 07203-000119

    Category Name: 2026 Fall Outfit Trends

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Upgrade High Rise Denim Mini Skort

    This skort was made for off-duty days that still deserve a killer outfit. The fitted denim silhouette and subtle side slit bring just the right amount of attitude.

    Fit & Features

    • Denim fabric
    • High-rise waist
    • Form-hugging fit
    • Side slit accent
    • Mini-length hem
    • Front button closure, belt loops
    • Four-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-000042

    Category Name: 2026 Fall Outfit Trends

    Price: $34.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

  • Own the Moment Patent Heeled Mules

    Strut like the sidewalk is your runway in these patent heeled mules! Perfect for dressing up your everyday slay or for a night out plans.

    Fit & Features

    • Short stiletto heel
    • Pointed toe
    • Luxe fit cushioned insole
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000029

    Category Name: 2026 Fall Outfit Trends

    Price: $30.90

    Availability: In Stock

    Available Color: BURGUNDY, BLACK

    Available Size: 5.5, 7, 7.5, 8, 10

    Product Badge:
    • Best Seller
  • Autumn Muse Off-The-Shoulder Sweater

    The sweater that nails cozy and confident. This off-the-shoulder sweater features a foldover neckline and a fitted, flattering shape that feels effortlessly chic. Perfect for pairing with capris, denim, or the classic skirt and tights combo.

    Fit & Features

    • Stretchy rib knit soft fabric
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Crop length hem
    • Runs true to size

    Style Number/Barcode: 06005-000219

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Not So Basic Long Sleeve Cutout Top

    Cozy meets daring with this ribbed knit cutout top. The asymmetric neckline and sleek fit make it your go-to for dressing up denim or pairing with a mini skirt.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • High neck, twisted strap, asymmetric cutout
    • Long fitted sleeves
    • Asymmetric mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-000210

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Allure Off-The-Shoulder Sweater

    Cozy but make it chic—this off-the-shoulder sweater brings a little drama with its foldover neckline and fitted silhouette. Pair it with denim and mules for that perfect fall-to-night-out look.

    Fit & Features

    • Soft knit stretch fabric
    • Fitted long sleeves
    • Folded off-the-shoulder neckline
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000214

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling For You Off-The-Shoulder Sweater

    The perfect sweater for crisp-air plans—this off shoulder ribbed knit sweater keeps things cozy with just the right hint of skin. Pair it with leather, denim, or your favorite latte for peak fall energy.

    Fit & Features

    • Soft ribbed knit fabric
    • Off shoulder foldover neckline
    • Long fitted sleeves
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-000215

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced Right Rib Knit Crop Top

    Cozy meets daring—this rib knit crop brings a snug fit with a lace-up neckline that does all the talking.

    Fit & Features

    • Rib knit fabric
    • Crew neckline
    • Fitted long sleeves
    • Lace-up front placket
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-000218

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Curve Line Sleeveless Rib Knit Top

    Minimal but never boring—this rib knit tank top plays it chic with a twist boat neckline and subtle cutout at the bust. The asymmetrical hem with slit detail makes it the kind of piece you’ll wear from coffee runs to casual dinner plans.

    Fit & Features

    • Rib knit stretch fabric
    • Boat neckline, twist and cutout accent
    • Fitted asymmetrical hem with slit
    • Runs true to size

    Style Number/Barcode: 06005-000217

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Stroll Off-The-Shoulder Sweater

    Crisp air, a latte, and this sweater—fall just called and said you’re its muse. The soft knit and off-the-shoulder neckline keep you cozy while looking chic for dinner meetups or casual dates.

    Fit & Features

    • Soft knit stretch fabric
    • Foldover, off-the-shoulder neckline
    • Fitted long sleeves
    • Crop length hem
    • Runs true to size

    Style Number/Barcode: 06005-000212

    Category Name: 2026 Fall Outfit Trends

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom With It Mid Rise Shorts

    Flirty and fun, these bloomer shorts bring an easy vibe with their mid-rise fit and cinched silhouette. Perfect for day or night!

    Fit & Features

    • Cotton-blend woven fabric
    • Mid-rise waist
    • Cinched elasticized silhouette
    • Short fitted hem
    • Runs true to size

    Style Number/Barcode: 06303-000040

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Crush Oversized Knit Cardigan

    The layer you’ll live in—this oversized crop cardigan is soft, slouchy, and effortlessly cute styled over your everyday look.

    Fit & Features

    • Soft knit fabric
    • Oversized long sleeves
    • Open front design
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000206

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale