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.

  • Disco Fever Metallic Platform Booties

    Bold, shiny, and sky-high, these metallic platform booties are here to make every outfit feel like a dance floor moment. Perfect for costume parties or themed events!

    Fit & Features

    • 5” block heel, 4.5” leg opening, 5.5” shaft
    • Square toe
    • Platform sole
    • Side zipper closure
    • Ankle length fit
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07403-000031

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • It-Girl Studded Shoulder Bag

    All eyes on you, always. This studded shoulder bag channels that it-girl glam with just the right amount of edge for your day-to-night lineup.

    Fit & Features

    • Patent faux leather material
    • Medium size
    • Long curved shoulder strap
    • All-over front studded accents
    • Woven lined interior, zippered pocket

    Style Number/Barcode: 07203-000106

    Category Name: 2026 Fall Outfit Trends

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Simplicity Bodycon Maxi Skirt

    No frills, no fuss—just pure silhouette. The smooth look, bodycon fit, and maxi hem give you an effortlessly pulled-together look that’s timeless yet modern. Pair with the matching top.

    Shop The Matching Top: Bold Simplicity Crop Tank Top

    Fit & Features

    • Double-lined slinky knit stretchy fabric
    • Mid-rise waist
    • Side ruched seams
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000076

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Check Me Out Ruffle Mini Skort

    Preppy meets playful in this ruffled plaid mini skort that’s serving major throwback charm. With built-in shorts and tiered layers, it’s perfect for latte runs, casual hangs, and stylish outfit posts.

    Fit & Features

    • Plaid print, knit fabric, stretchy shorts lining
    • Mid-rise waist
    • Tiered ruffled silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-000168

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dot to Trot Polka Dot Mini Dress

    Playful yet polished, this polka dot mini dress hugs in all the right places. With its sweetheart neckline and curve-hugging fit, it’s a flirty staple for last-minute plans or casual brunches!

    Fit & Features

    • Polka dot print, mesh-lined fabric
    • Sweetheart neckline
    • Spaghetti straps
    • Curve-hugging fit
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000437

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hide And Chic Ruffle Shorts

    Ruffles meet rebellion. These camouflage print hot shorts blend flirty layers with a wild twist—made for lounging, layering, or turning your chill day into a cute-day moment.

    Fit & Features

    • Camouflage print, mesh-lined fabric, moderate stretch
    • Mid-rise waist
    • Tiered ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 06503-000166

    Category Name: 2026 Fall Outfit Trends

    Price: $29.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L

  • Preppy Play Plaid Bloomer Shorts

    These plaid bloomer shorts give lounge-meets-street vibes with their relaxed fit and gathered hem—perfect for pairing with an oversized tee, chunky sweater, or your “just rolled out but still cute” mood.

    Fit & Features

    • Plaid print, chiffon fabric, sewn-in woven lining
    • Mid-rise waist with bow accent
    • Smocked form-hugging silhouette
    • Ruffled trim hem
    • Runs true to size

    Style Number/Barcode: 06503-000162

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Frills Lace Romper

    Flirt mode: on. This strapless lace romper is the perfect mix of sweet and sultry, finished with a ruffled hem that’s made for twirling through fall nights or layering under a blazer for date night.

    Fit & Features

    • Lace fabric, knit shorts lining
    • Strapless neckline with bow
    • Form-hugging bodice
    • Layered ruffled skirt overlay
    • Runs true to size

    Style Number/Barcode: 06503-000165

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Polish High-Rise Flare Trouser Pants

    Sleek, sculpted, and made to move with you. These high-waist flare pants blend polished tailoring with a flattering seam detail—perfect for dressing up your 9-to-5 or elevating your weekend look.

    Fit & Features

    • Smooth woven fabric
    • High-rise waist, belt loop accents
    • Hidden front zipper and hook-eye fasteners
    • Hip-hugging fit
    • Seam detailing down the front
    • Flare hem
    • Runs true to size

    Style Number/Barcode: 06402-000012

    Category Name: 2026 Fall Outfit Trends

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Chic Confidence High Slit Mesh Midi Skirt

    When subtle isn’t the move, this mesh midi skirt delivers. With a thigh-high slit and ruched waist, it’s the kind of style that owns the night and brings the confidence.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • High-rise waist, ruching
    • Ultra-high front slit
    • Asymmetric midi-length hem
    • Flowy fit
    • Runs true to size

    Style Number/Barcode: 06501-000075

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Intentions Pleated Denim Mini Skort

    She’s giving ‘effortless but planned.’ This pleated denim mini skort brings that flirty Y2K energy with just the right amount of edge—perfect for styling with your favorite sweater or baby tee.

    Fit & Features

    • Denim fabric
    • Mid-rise waist
    • Drop waist design, belted accent
    • Pleated mini-length overlay with front slit, A-line fit
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06603-000118

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wildly Flirty Zebra Print Tube Top

    Go wild with this zebra print tube top that was made for fearless 'fits. The sheer mesh, hardware accent, and flyaway front keep it flirty and fun for your next all-night look.

    Fit & Features

    • Sheer mesh fabric, lined bust, high stretch
    • Zebra print
    • Strapless sweetheart neckline, no-slip strip
    • Curved metal hardware accent at the bust
    • Front flyaway design
    • Cropped hem, flowy fit
    • Runs true to size

    Style Number/Barcode: 06001-000283

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Eyes On You Faux Leather Skort

    When a mini just won’t cut it—this buckle skort brings the edge with extra attitude. Sleek, structured, and made for going out, it’s your instant cool-girl staple.

    Fit & Features

    • Faux leather fabrication
    • Statement buckle
    • Skort silhouette with mini length
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06403-000076

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strut In Style Scrunch Over-The-Knee Boots

    Strut like you mean it—these scrunch over-the-knee boots were made for bold entrances. With a sleek stiletto heel and form-hugging fit, they’re the ultimate power move for nights out.

    Fit & Features

    • Stiletto heel
    • Closed pointed toe
    • Over-the-knee height
    • Scrunched design
    • Complete inner zipper closure
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000095

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $50.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Polished Edit Plaid Blazer

    For the girl who plans her power moves and her outfits. This plaid blazer pulls any look together with a polished, structured fit that means business (but still plays it cool). Style with the matching mini skort.

    Shop Matching Bottoms: Polished Edit Plaid Pleated Mini Skort

    Fit & Features

    • Woven fabric with woven lining, plaid pattern
    • Lapel collar
    • Long sleeves
    • Single-breasted design
    • Dual front pockets
    • Structured silhouette with relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-000072

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Scene Corduroy Shorts

    Cozy texture, cool-girl fit. These corduroy shorts are soft, fitted, and made for easy styling—perfect for pairing with tights and boots or keeping it casual with a sweater and sneakers.

    Fit & Features

    • Soft corduroy fabric
    • Mid-rise waistline
    • Front zipper and button closure
    • Side and back pockets
    • Runs true to size

    Style Number/Barcode: 06603-000116

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Allure Long Sleeve Slit Midi Dress

    Your new go-to for looking polished without even trying. This hacci rib knit midi dress serves up a body-skimming fit, cozy texture, and a side slit for just the right amount of edge. Perfect for everything from PSL runs to dinners downtown.

    Fit & Features

    • Soft hacci rib knit stretch fabric
    • Sweetheart neckline
    • Fitted long sleeves
    • Side slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000301

    Category Name: 2026 Fall Outfit Trends

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dangerously Divine Long Sleeve Bodycon Dress

    Bring the heat—this long sleeve bodycon dress is bold, fitted, and ready to steal the night. The sleek ruching and daring neckline make it perfect for dressy events and date nights.

    Fit & Features

    • Smooth knit stretch fabric
    • V-neckline
    • Fitted long sleeves
    • Ruched detail
    • Bodycon fit, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000308

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daydream Date Bow-Front Skater Dress

    Giving total daydream vibes with a flirty twist. The bow-front detail and breezy skater silhouette make this short dress perfect for brunch, strolls, or spontaneous golden-hour photo ops.

    Fit & Features

    • Satin woven fabric, scenic print
    • Sleeveless V-neckline, bow-front detail
    • Adjustable spaghetti straps, smocked back
    • High-rise waist
    • Short skater silhouette, striped hem
    • Runs true to size

    Style Number/Barcode: 05102-000306

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Steps Leopard Kitten Mules

    These leopard mules are sleek, bold, and endlessly chic. The pointed toe and low heel make them perfect for office hours to cocktail hour!

    Fit & Features

    • Kitten stiletto heel
    • Closed pointed toe
    • Cushioned insole
    • Leopard pattern
    • Runs true to size

    Style Number/Barcode: 07401-000529

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Prowl Mesh Leopard Kitten Pumps

    Step out boldly in these mesh leopard pumps showcasing a closed-toe design and sleek kitten heel that dresses up your day or night look.

    Fit & Features

    • Kitten heel
    • Pointed toe
    • Closed design
    • Faux leather insole
    • Mesh material with leopard print
    • Runs true to size

    Style Number/Barcode: 07401-000531

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rebel Chic Buckle Kitten Heels

    These aren’t your average heels—pointed toes, edgy grommet straps, and bold buckle details bring instant attitude. Perfect for taking your outfit from low-key to don’t mess with me in one step.

    Fit & Features

    • Kitten heel
    • Closed pointed toe with buckled strap
    • Thin grommet-embellished strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000530

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Street Zipper Moment Denim Skirt

    This mid-rise denim skirt turns every sidewalk into a runway with bold zipper details that strike the perfect balance between edgy and wearable. Pair it with boots, sneakers, or your boldest top.

    Fit & Features

    • Denim fabric
    • Mid-rise waist
    • Multi-zipper detailing
    • Structured pleated silhouette
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 06601-000022

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Energy Zebra Print Denim Mini Skort

    A mini skort with attitude—this zebra print denim instantly flips your outfit into something bold, confident, and impossible to overlook. It’s the style you grab when you’re craving bold energy that still feels effortless.

    Fit & Features

    • Denim fabric
    • Zebra print
    • Mid-rise waist, belted design
    • Dual front button closures, back zipper closure 
    • Mini-length overlay
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06603-000115

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free