2026 Fall Outfit Trends
From sweater dresses to pleated mini skirts with tights, these fall outfit ideas are made to mix, match, and layer on repeat. Try a sweeping maxi skirt with a belted jacket for a modern boho look, or layer a tie-front cardigan over your go-to mini with hosiery and boots for a polished finish. Add a statement sweater or bomber jacket to pull any look together. Rich tones like brown, burgundy, tan, and black keep every outfit sleek and autumn-ready.
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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.
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Sleek Club Faux Leather Bomber Jacket
Fall layers with a streetwear-inspired vibe. This faux leather bomber leans into streetwear with a relaxed shape, high neck, and sleek finish that works for effortless styling.
Fit & Features
- Faux leather fabric, smooth lining
- Long sleeves
- Relaxed bomber silhouette
- High neckline, front snap-button closures
- Side pockets and elasticized hem
- Runs true to size
Style Number/Barcode: 06204-000183
Category Name: 2026 Fall Outfit Trends
Price: $69.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
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Wild Card Snake Print Statement Necklace
Your neckline just got a little wilder. This snake-print statement necklace mixes bold geometric links with an adjustable fit for the kind of finishing touch that makes even a basic outfit look fully planned.
Fit & Features
- Metal construction with faux snakeskin print panels
- Linked geometric statement design
- Lobster clasp with adjustable extender chain
Style Number/Barcode: 07002-000625
Category Name: 2026 Fall Outfit Trends
Price: $18.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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City Plans Moto Jacket
City plans called for something with a little edge. This cropped moto jacket brings structured denim, sharp seaming, and zip details that instantly make even a simple top feel more styled.
Shop Matching Skort: City Plans Mid-Rise Skort
Shop Matching Pants: City Plans Wide-Leg PantsFit & Features
- Structured denim fabric
- Cropped moto jacket silhouette
- Stand collar with front zip closure
- Seamed construction with zip sleeve details
- Long sleeves
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-000177
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
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Fall Forecast Denim Trucker Jacket
The layer your fall lineup was waiting for. This denim jacket brings an easy oversized feel, zip front, and oversized fit that make every outfit feel instantly more season-ready.
Fit & Features
- Structured denim fabric
- Collar neckline
- Relaxed trucker silhouette with long sleeves
- Zip front closure with flap pockets
- Oversized fit
- Runs true to size
Style Number/Barcode: 06203-000064
Category Name: 2026 Fall Outfit Trends
Price: $46.90
Availability: In Stock
Available Color: MED, DENIM
Available Size: S, M, L
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Plans in Motion Ruched Asymmetrical Midi Skirt
Not your basic midi, and that’s exactly why it works. Ruched detailing and an adjustable drawstring shape the waist, while the asymmetrical hem brings just enough movement for dinner plans, drinks, and whatever happens after.
Fit & Features
- Soft stretch fabrication
- Mid-rise waist
- Ruched waistband with adjustable drawstring
- Asymmetrical handkerchief hem
- Runs true to size
Style Number/Barcode: 06501-000201
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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City Plans Mid-Rise Skort
Your mini moment, minus the outfit stress. This denim skort keeps the look clean and fitted with built-in shorts underneath, so you can take it from daytime wandering to late dinner plans without overthinking it.
Shop Matching Jacket: City Plans Moto Jacket
Shop Matching Pants: City Plans Wide-Leg PantsFit & Features
- Structured twill fabrication
- Mid-rise waist
- Classic five-pocket styling
- Mini length hem
- Built-in shorts
- Runs true to size
Style Number/Barcode: 06303-000066
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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City Plans Wide-Leg Pants
City plans, but make the bottom half effortless. These wide-leg pants sit sleek through the waist before falling into an easy, elongated shape that works just as well with the matching moto jacket as it does with a fitted top and heels.
Shop Matching Jacket: City Plans Moto Jacket
Shop Matching Skort: City Plans Mid-Rise SkortFit & Features
- Structured twill fabric
- Mid-rise waist
- Contoured waistband
- Back zip closure
- Wide-leg hem
- Runs true to size
Style Number/Barcode: 06302-000025
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Off Duty Agenda Faux Leather Zip Jacket
Cool weather plans just found their plus one. This faux leather jacket brings a cropped fit, sharp collar, and clean zip front that layers just as easily over a baby tee as it does a night-out look.
Fit & Features
- Faux leather construction, sewn-in woven lining
- Cropped jacket silhouette
- Point collar neckline
- Front pockets
- Front zip closure with seam detailing
- Runs true to size
Style Number/Barcode: 06204-000171
Category Name: 2026 Fall Outfit Trends
Price: $59.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
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Strut Intent Faux Leather Boots
The outfit just found its finishing move. These sleek knee-high boots pair a sleek faux leather silhouette with a sturdy block heel for dresses, minis, and denim days that need more attitude.
Fit & Features
- 4” Block heel, 7” leg opening, 15” shaft
- Square toe
- Side zipper closure
- Fitted knee-high silhouette
- Sleek faux leather material
- Runs true to size
Style Number/Barcode: 07402-000157
Category Name: 2026 Fall Outfit Trends
Price: $48.90
Availability: In Stock
Available Color: BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
Product Badge: -
Plans on Point Patent Strappy Wedge Sandals
Your going-out lineup just found its finishing move. These glossy patent wedge sandals pair a sleek open toe with slim wraparound ankle straps and a sculpted wedge heel for an elevated look that still feels easy.
Fit & Features
- Glossy patent faux leather
- Open pointed toe silhouette
- Slim wraparound ankle straps with buckle closure
- Sculpted wedge heel
- Runs true to size
Style Number/Barcode: 07406-000048
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: In Stock
Available Color: PLUM
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9
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Fall For It Lace Up Corset Crop Top
A little romantic, a little undone. This lace-up corset crop top brings a deep V neckline, sheer sleeves, and a fitted cropped shape that makes jeans and heels feel way more intentional.
Fit & Features
- Lightweight woven fabric
- Deep V neckline
- Sheer long sleeves with tie cuffs
- Lace-up corset front with cropped hem
- Runs true to size
Style Number/Barcode: 06003-000287
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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Closed Case Frog Closure Crop Top
Proof that the smallest details can carry the whole fit. This ribbed crop top features a fitted silhouette, split neckline, and statement frog closures that make jeans, minis, and low-rise bottoms feel instantly more styled.
Fit & Features
- Ribbed knit fabric
- Split neckline
- Short sleeves
- Decorative frog front closures
- Runs true to size
Style Number/Barcode: 06002-000686
Category Name: 2026 Fall Outfit Trends
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: L
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Polished Plans Horsebit Slingback Heels
A little prep, a little edge, fully put together. These pointed-toe slingback heels feature sleek horsebit hardware and a sculpted heel for an elevated finish that works from desk plans to dinner plans.
Fit & Features
- Smooth faux leather upper
- Pointed toe silhouette
- Horsebit hardware accent
- Slingback strap with sculpted heel
- Runs true to size
Style Number/Barcode: 07401-000927
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: In Stock
Available Color: IVORY, BLACK
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Golden Hour Hammered Oval Statement Earrings
The easiest way to make a simple outfit look way more considered. These hammered oval statement earrings bring sculptural texture and a bold silhouette that works just as well with a sleek dress as it does with denim and a fitted top.
Fit & Features
- Metal construction
- Hammered oval silhouette
- Sculptural statement design
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000531
Category Name: 2026 Fall Outfit Trends
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Next Level Velcro Wedge Sneakers
Sneaker comfort, with a little extra height built in. These wedge sneakers bring a sporty high-top silhouette, triple velcro straps, and a hidden wedge heel for an easy streetwear switch-up with denim, cargos, or a mini.
Fit & Features
- Mixed faux suede and faux leather upper
- High-top sneaker silhouette
- Triple velcro strap closure
- Hidden wedge heel with rubber sole
- Runs true to size
Style Number/Barcode: 07407-000005
Category Name: 2026 Fall Outfit Trends
Price: $35.90
Availability: In Stock
Available Color: BROWN, BEIGE
Available Size: 6, 7, 8, 9, 10, 5
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Off Duty Polish Ruched Mock Neck Sleeveless Top
Easy base layer, polished payoff. This sleeveless mock-neck top keeps the silhouette sleek with soft ruching through the waist, making it a solid pick for denim, tailored bottoms, or a mini when you want the outfit to feel pulled together fast.
Fit & Features
- Soft stretch knit fabric
- Mock neckline
- Sleeveless fitted silhouette
- Ruched side detailing
- Runs true to size
Style Number/Barcode: 06002-000667
Category Name: 2026 Fall Outfit Trends
Price: $19.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: S, M, L
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Weekend Detour Suede Cabby Hat
This faux suede cabby hat brings a soft, vintage-inspired shape with a short brim and button details for an easy finish to your fall looks.
Fit & Features
- Structured cabby hat silhouette
- Short curved brim
- Decorative band with button accents
- Soft faux suede material, sewn-in lining
Style Number/Barcode: 07302-000356
Category Name: 2026 Fall Outfit Trends
Price: $16.90
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Shift Off Shoulder Knit Top
A one-shoulder neckline changes the whole outfit formula. The knit top pairs a soft blouson shape with a fitted hem that pairs perfectly with high-rise bottoms.
Fit & Features
- Knit fabrication
- Asymmetrical off-the-shoulder neckline
- Short sleeves
- Relaxed blouson-style upper shape
- Fitted waist-length hem
- Runs true to size
Style Number/Barcode: 06005-000440
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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Glossed Up Patent Knee High Stiletto Boots
Consider your outfit officially sharpened. These glossy knee-high boots bring a pointed toe and slim stiletto heel to minis, denim, and every night-out look in between.
Fit & Features
- Glossy faux leather
- Knee-high silhouette
- Pointed toe
- Stiletto heel with inner zipper closure
- Runs true to size
Style Number/Barcode: 07402-000185
Category Name: 2026 Fall Outfit Trends
Price: $46.90
Availability: In Stock
Available Color: TAN, RED
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Ring Leader Micro Mini Tote Bag
Handle the plans like you booked the table. This structured micro mini bag brings polished shape, ring handles, and a detachable chain strap for versatile styling with any look.
Fit & Features
- Micro mini structured silhouette
- Ring handles
- Detachable chain strap
- Holds small, loose items
- Faux leather material
Style Number/Barcode: 07201-000050
Category Name: 2026 Fall Outfit Trends
Price: $17.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Fast Lane Buckled Moto Knee High Boots
Your fall lineup just got a little tougher. These knee-high moto boots bring stacked buckle straps, metal hardware, and a low block heel for that streetwear edge that works with minis, denim, and oversized layers.
Fit & Features
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2” heel, 7.5” leg opening, 13” shaft
- Faux leather
- Knee-high moto silhouette
- Multi-buckle strap detailing with metal hardware
- Rounded toe with low block heel
- Runs true to size
Style Number/Barcode: 07402-000206
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: 6, 7, 8, 9, 10
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2” heel, 7.5” leg opening, 13” shaft
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Sleek Silhouette Butterfly Print Maxi Dress
Butterflies, but make it sleek. This high-stretch mesh maxi dress hugs the figure with a bodycon fit, while the abstract butterfly print and mock neckline keep the look artful, elevated, and ready for plans.
Fit & Features
- Mesh fabric, high stretch
- Abstract butterfly print
- Sleeveless mock neckline
- Tank shoulder straps
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000847
Category Name: 2026 Fall Outfit Trends
Price: $42.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Ruffle Romance Lace-Trim Chiffon Maxi Dress
Pretty, layered, and a little dramatic. This lace-trim chiffon maxi dress flows with a tiered ruffle silhouette, adjustable spaghetti straps, and a tie-front V-neckline for an easy dressed-up feel.
Fit & Features
- Lined chiffon fabric, lace trim
- Sleeveless V-neckline, tie-front detail
- Adjustable spaghetti straps
- Back zipper closure
- Tiered ruffled silhouette
- Maxi-length A-line fit
- Runs true to size
Style Number/Barcode: 05101-001413
Category Name: 2026 Fall Outfit Trends
Price: $64.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L
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Little Drama Polka Dot Mesh Midi Skirt
Dots with a little drama built in. This semi-sheer mesh midi skirt brings movement with a flowy A-line fit, high cut side slit, and hanky-style hem made for going out looks that deserve a little extra.
Fit & Features
- Semi-sheer mesh fabric with knit panty lining, high stretch
- Polka dot print
- Mid-rise waist
- High-cut side slit
- Midi-length hanky-style hem
- Flowy A-line fit
- Runs true to size
Style Number/Barcode: 06501-000198
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: XS, S, M, L
