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.

  • Polished Intent Patent Mules

    Serving sophistication with a side of attitude. These patent mules feature a sleek pointed toe and a sculpted heel that takes you from dinner to downtown without missing a step. 

    Fit & Features

    • 3" Stiletto heel
    • Closed pointed-toe
    • Luxe fit cushioned insole
    • Faux leather patent material
    • Runs true to size

    Style Number/Barcode: 07401-000414

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Ice Queen Removable Faux Fur Denim Jacket

    Cooler weather, elevated. This cropped denim jacket brings a luxe twist with its removable faux fur collar and cuffs—soft, plush, and totally statement-making. Pair it with sleek basics or layer it over a party dress for that “it-girl” vibe.

    Fit & Features

    • Denim cotton fabric, sewn-in woven lining
    • Removable faux fur collar neckline
    • Long sleeves with removable faux fur cuffs
    • Single snap-button front closure
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06203-000023

    Category Name: 2026 Fall Outfit Trends

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In The Bag Bow Shoulder Purse

    Girly meets polished—this faux leather shoulder bag gets a sweet twist with bow accents at the sides. Compact and versatile, it’s the kind of arm candy that dresses up any look effortlessly.

    Fit & Features

    • Adjustable shoulder strap
    • Side bow accents
    • Top zipper closure
    • Lined spacious interior with zipper pocket
    • Faux leather material

    Style Number/Barcode: 07203-000185

    Category Name: 2026 Fall Outfit Trends

    Price: $25.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: NS

  • Polished Edge Shoulder Bag

    Classic with a cool-girl edge—this faux leather shoulder bag features a signature horsebit chain detail that elevates any look. It’s the perfect blend of timeless and trendy for your everyday rotation.

    Fit & Features

    • Top shoulder strap
    • Front flap, snap-button closure, horsebit chain detail
    • Lined spacious interior
    • Faux leather material

    Style Number/Barcode: 07203-000067

    Category Name: 2026 Fall Outfit Trends

    Price: $11.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortlessly Iconic Denim Mini Skirt

    Your go-to mini skirt for the moments when effortless ends up looking iconic. The denim mini silhouette adds that casual cool factor whether you’re running errands or going on a night out.

    Fit & Features

    • Denim fabric
    • Mid-rise waist, belt loops
    • Front button closure
    • Dual front flap pockets, button closures, dual back pockets
    • Mini-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06601-000019

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Streak Faux Suede Block Heels

    When your shoes need to bring just as much drama as your outfit—these block heel sandals deliver with a glam hardware accent and sleek ankle strap. Perfect for pairing with everything from minis to wide-leg pants.

    Fit & Features

    • 4" Block heel
    • Almond toe
    • Twist strap with hardware trim
    • Adjustable ankle strap with buckle closure
    • Cushioned insole
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07401-000404

    Category Name: 2026 Fall Outfit Trends

    Price: $30.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daydream Darling Satin A-Line Mini Dress

    Romantic lines, flirty details—this strapless satin mini dress is a total heart-stealer. The lace trim and A-line flow make it perfect for date nights, parties, or just feeling extra pretty.

    Fit & Features

    • Textured satin woven fabric
    • Strapless sweetheart neckline, lace trim
    • Ruched bust, tie-front accent, corset-style bodice
    • Partially smocked back, zipper closure
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000534

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Slip Into Bloom Lace-Up Floral Maxi Dress

    Serving soft drama with every step. From the draped neckline to the lace-up slit, this floral maxi knows how to bring a flirtatious allure, perfect for date nights, vacation, or shower celebrations!

    Fit & Features

    • Floral print, smooth knit-lined fabric, moderate stretch
    • Cowl neckline
    • Spaghetti straps
    • Lace-up back
    • High side slit
    • Curve-hugging silhouette, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000532

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Season’s Sleek Thigh-High Stiletto Boots

    The definition of drama. These scrunch thigh-high boots strike the perfect balance of luxe and daring, with a pointed toe and sleek stiletto heel made to elevate all your fall outfits.

    Fit & Features

    • 3” stiletto heel, 9.5” leg opening, 23” shaft
    • Pointed-toe
    • Side zipper closure
    • Thigh-high scrunch silhouette
    • Sleek faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000062

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $58.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Street Circuit High-Rise Wide Leg Denim Jeans

    These denim jeans don’t just walk—they strut. The dual-sided zips and contrast paneling bring a moto-meets-street vibe, while the wide-leg cut keeps it effortlessly cool. Complete the vibe with a crop jacket and sneakers.

    Fit & Features

    • Medium wash denim cotton-blend fabric, non-stretch
    • High-rise waist
    • Dual side zip-up details with contrast paneling
    • Wide-leg silhouette
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06602-000071

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Intentions Slingback Heels

    Effortless sophistication, start to finish. These faux suede slingback heels blend a sharp pointed toe with a classic stiletto heel—perfect for elevating your day or night look.

    Fit & Features

    • 4" Stiletto heel
    • Closed pointed-toe
    • Slingback adjustable ankle strap, buckle closure
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07401-000398

    Category Name: 2026 Fall Outfit Trends

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
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  • Street Style Cargo Mini Skort

    Utility with a flirty twist. This belted mini skort serves up cargo pockets and a curve-skimming fit that’s perfect for pairing with crop tops, tanks, or oversized layers.

    Fit & Features

    • Cotton-blend denim fabric, minimal stretch
    • Belted mid-rise waist
    • Dual front button and zipper closure
    • Dual front pockets, dual back cargo pockets
    • Form-hugging fit
    • Mini-length overlay, hidden shorts lining
    • Runs true to size

    Style Number/Barcode: 06603-000105

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Layers of Luxe Teardrop Cubic Zirconia Necklace

    Instantly elevated—this layered chain necklace shines with mixed textures and a delicate teardrop pendant that adds just the right touch of glam. Perfect for stacking with more chains or letting it shine solo.

    Fit & Features

    • Three-row design
    • Mixed layered chains
    • Teardrop cubic zirconia pendant
    • Lobster clasp closure with extender

    Style Number/Barcode: 07002-000118

    Category Name: 2026 Fall Outfit Trends

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slick Moves Faux Leather Pleated Skort

    This skort shows up polished but never boring. The sleek finish and sharp pleats give you that put-together feel, whether you’re styling it casual or leaning all the way into a night-out look.

    Fit & Features

    • Smooth faux leather fabric
    • High-rise drop waist silhouette
    • Pleated skort design with built-in fitted shorts
    • Mini length hem
    • Pull-on style
    • Runs true to size

    Style Number/Barcode: 06403-000058

    Category Name: 2026 Fall Outfit Trends

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Frontier Chic Moto Boots

    Bring the western energy into your fall lineup with these knee-high boots. Featuring harness buckle detailing, a pointed toe, and a block heel, they bring western flair to a city chic vibe, perfect for styling with any look.

    Fit & Features

    • 3" Block heel, 8" leg opening, 13" shaft height
    • Pointed-toe
    • Harness buckle detailing
    • Knee-high shaft length
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000056

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $65.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Attitude Strut Patent Stiletto Boots

    When the outfit needs attitude—these boots deliver. With a glossy patent finish, sleek pointed toe, and knee-high silhouette, they’re basically confidence in footwear form. Perfect for days downtown, date nights, and everyday styling.

    Fit & Features

    • 2" Stiletto heel, 7.5" leg opening, 13" shaft height
    • Pointed-toe
    • Side zipper closure
    • Under-the-knee length shaft
    • Glossy patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-000060

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Revival Faux Leather Mary Janes

    A classic with a twist—these slingback Mary Janes bring vintage vibes into the now with a block heel and sleek faux leather finish. Perfect with trousers, minis, or tights for that polished-cool look.

    Fit & Features

    • 3.5" Block heel
    • Closed square toe
    • Slingback strap with adjustable buckle closure
    • Mary Jane silhouette
    • Luxe fit cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000386

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Essential Faux Leather Belt Set

    Cinch it, style it, own it—this three-piece belt set has your fits covered. With three versatile faux leather belts and sleek gold buckles, it’s basically your outfit’s new BFF.

    Fit & Features

    • Three-piece set
    • Faux leather material
    • Buckle closure
    • Adjustable fit

    Style Number/Barcode: 07301-000182

    Category Name: 2026 Fall Outfit Trends

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Mood Tie Dye Halter Maxi Dress

    Made for chasing sunsets. This cowl halter maxi dress flows with an abstract tie dye print and curve-hugging silhouette that’s perfect for sunset cocktails on vacay and summer date nights!

    Fit & Features

    • Abstract tie-dye print, mesh-lined fabric
    • Cowl halter neckline
    • Open back
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000504

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blue Crush Denim Halter Skater Dress

    Meet your new denim obsession. This square neck halter mini dress serves curve-hugging confidence with belted detailing and flirty side cutouts made for catching glances.

    Fit & Features

    • Stretch denim fabric, knit panty lining
    • Adjustable belted halter square neckline, foldover accent
    • Back zipper and hook-eye closure
    • Side waist cutouts
    • Front seam detailing
    • Skater short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000241

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Handle It O-Ring Mini Tote Bag

    Polished and practical—this mini tote bag keeps it minimal with a structured faux leather body and bold O-ring handle, perfect for dressing up any look.

    Fit & Features

    • Top O-ring handles
    • Detachable chain strap
    • Sleek and structured silhouette
    • Snap-button closure
    • Lined spacious interior
    • Smooth faux leather material

    Style Number/Barcode: 07203-000048

    Category Name: 2026 Fall Outfit Trends

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Downtown Girl Faux Leather Sherpa Crop Jacket

    For the girl who’s always on the move (and always looks good doing it). This cropped faux leather jacket with plush sherpa lining brings that downtown ease—structured, soft, and effortlessly elevated. It’s the jacket that makes even a coffee run feel like a moment.

    Fit & Features

    • Faux leather fabric, faux sherpa plush lining
    • Faux sherpa collar neckline
    • Long sleeves, faux sherpa cuffs
    • Front zip-up closure
    • Front pockets
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06201-000027

    Category Name: 2026 Fall Outfit Trends

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Checkmate Plaid Mini Skort

    Preppy with a playful twist. This plaid mini skort features front button details and a fitted waist, giving you that polished-yet-flirty vibe—perfect for pairing with the matching trench vest.

    Shop Matching Vest: Checkmate Plaid Trench Vest

    Fit & Features

    • Plaid pattern, faux wool-lined fabric
    • High-rise waist, button closures
    • Front flap pockets
    • Bodycon fit
    • Mini-length hem, shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-000056

    Category Name: 2026 Fall Outfit Trends

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chill Luxe Faux Fur Crop Vest

    Your cold weather layering just got a luxe upgrade. This faux fur crop vest is cozy-chic with its sleeveless cut and handy pockets—perfect for tossing over knits or long sleeves when the vibe calls for plush drama.

    Fit & Features

    • Plush faux fur, sewn-in woven lining
    • Sleeveless collared neckline
    • Side pockets
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06201-000019

    Category Name: 2026 Fall Outfit Trends

    Price: $14.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free