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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London Calling Studded Graphic Top
The studded London graphic gives this top plenty of attitude before you add a single accessory. The fitted shape and off-the-shoulder styling keep the silhouette sharp while the short sleeves make it easy to pair. Style it with plaid trousers or low-rise denim to lean into the city-girl edge.
Fit & Features
- Knit cotton-blend fabric, moderate stretch
- Off-the-shoulder neckline
- Short sleeves
- "London" graphic with stud detailing
- Mid-length hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06002-000713
Category Name: 2026 Fall Outfit Trends
Price: $26.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Polished Plans Belted Crop Trench Coat
Consider your layering game officially pulled together. This belted trench coat pairs a draped shawl collar with a self-tie waist for an effortlessly polished shape that works from weekday plans to dressed-up moments.
Fit & Features
- Faux wool fabric, sewn-in woven lining
- Draped shawl collar neckline
- Long sleeves
- Tie-waist belt, front pockets
- Crop-length silhouette
- Runs true to size
Style Number/Barcode: 06201-000126
Category Name: 2026 Fall Outfit Trends
Price: $64.90
Availability: In Stock
Available Color: WINE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Street Shift Zip Front Faux Leather Bomber Jacket
This faux leather bomber jacket brings a sharper finish to a classic shape. The textured surface and zip front add structure, while the collared neckline and elasticized trim keep the relaxed silhouette clean. Pair it with fitted bottoms or lace layers to play up the contrast.
Fit & Features
- Collared neckline
- Front zipper closure
- Textured faux leather finish
- Long sleeves
- Elasticized cuffs and hem
- Runs true to size
Style Number/Barcode: 06204-000207
Category Name: 2026 Fall Outfit Trends
Price: $59.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Polished Plans Longline Trench Coat
Consider this your answer to looking put together in five seconds. This longline trench coat brings a tailored lapel, clean button front, and relaxed silhouette that layers easily over knits, minis, and cold-weather looks.
Fit & Features
- Soft faux wool fabric, lining
- Lapel collar neckline
- Long sleeves
- Button-front closures
- Front pockets
- Long-line trench silhouette
- Runs true to size
Style Number/Barcode: 06201-000120
Category Name: 2026 Fall Outfit Trends
Price: $64.90
Availability: In Stock
Available Color: OATMEAL, BLACK
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Check Please Plaid Belted Mini Skort
Plaid just found its trendy flair. This belted mini skort looks like a skirt with the ease of shorts, ready for campus days, coffee runs, and last-minute plans. Style with the matching halter top.
Shop Matching Top: Check Please Plaid Halter Top
Fit & Features
- Plaid-printed woven fabric
- Mid-rise waist with belted accents
- Side zipper closure
- Pleated, flared, A-line silhouette
- Mini-length hem
- Built-in knit shorts lining
- Runs true to size
Style Number/Barcode: 06403-000197
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Part of a Set
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Cozy Drama Cropped Faux Fur Knit Bolero
This cropped faux fur bolero is the layer that changes the whole outfit. The open front, long sleeves, and faux fur trim make it easy to throw over a fitted top when you want a little more texture. Pair it with relaxed denim or a mini to keep the proportions sleek.
Fit & Features
- Open-front bolero silhouette
- Faux fur trim at neckline
- Long fitted sleeves, faux fur cuffs
- Ultra-cropped length
- Runs true to size
Style Number/Barcode: 06202-000145
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
- Open-front bolero silhouette
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Sleek Fold Off Shoulder Maxi Dress
This silhouette keeps things smooth from top to hem. A fitted rib knit shape is framed by a foldover off-the-shoulder neckline, giving the maxi dress a long, streamlined look. The back slit adds just enough movement to finish it off.
Fit & Features
- Soft rib knit fabric with high stretch
- Foldover off-the-shoulder neckline
- Long sleeves
- Bodycon silhouette
- Back center slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000465
Category Name: 2026 Fall Outfit Trends
Price: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Gloss Move Faux Leather Mini Skort
Keep the base sleek and build from there. This faux leather mini skort brings a bodycon fit and sleek finish that pairs easily with chic tights, knit sweaters, and knee-high boots. Add a cropped jacket when you want the look to feel a little sharper.
Fit & Features
- Faux leather fabric, built-in stretchy knit shorts lining
- High-rise waist
- Side zipper closure
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06403-000193
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Waist Shift Low-Rise Twill Mini Skort
Low-rise is back in rotation, and this skort keeps the update clean. The twill mini shape pairs slant pockets with a streamlined waist for a sharper take on the throwback silhouette. The result feels current without overworking the trend.
Fit & Features
- Twill fabric
- Low-rise fit
- Button-front waistband with zip-fly closure
- Front slant pockets
- Fitted mini-length overlay
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06303-000073
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Desk Mode Aviator Glasses
Consider your screen time officially better accessorized. These glasses feature an oversized aviator silhouette, clear lenses, and a sleek patterned frame that gives workday styling a cooler point of view.
Fit & Features
- Oversized aviator silhouette
- Clear lenses
- Patterned full rim frame
- Double bridge detail
- Slim temple arms
Style Number/Barcode: 07008-000290
Category Name: 2026 Fall Outfit Trends
Price: $12.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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Cargo Call Utility Pocket Jorts
Cargo jorts are stepping into the trend cycle with a sharper utility edge. The relaxed knee-length shape keeps the silhouette easy, while stacked flap pockets bring in the detail-heavy look that’s everywhere right now. It’s a fresh way to work utility styling without overdoing it.
Fit & Features
- Woven fabric
- Mid-rise waist, belt loops
- Front pockets
- Hidden front hook and eye with zipper closure
- Multiple cargo flap pockets
- Relaxed knee-length silhouette
- Utility-inspired design
- Runs true to size
Style Number/Barcode: 06303-000071
Category Name: 2026 Fall Outfit Trends
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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City-Bound Faux Leather Cinched Waist Bomber Jacket
City-bound and looking chic. This faux leather bomber jacket brings a polished edge with a high mock neckline, zip front, and adjustable cinched waist that lets you switch up the shape.
Fit & Features
- Faux leather fabric, sewn-in woven lining
- High mock neckline
- Long sleeves with snap-button closures
- Chest pockets
- Zip-front design
- Adjustable drawcord cinched waist
- Runs true to size
Style Number/Barcode: 06204-000206
Category Name: 2026 Fall Outfit Trends
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Best Seller
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Flirty In Plaid Mesh Ruffle Mini Skort
Plaid just got a little more flirtatious. This mesh mini skort hugs the waist with ruched detailing and features a mini-length overlay with a ruffled side accent that makes the matching halter top feel instantly more styled.
Shop Matching Top: Flirty In Plaid Mesh Halter Top
Fit & Features
- Plaid-printed mesh fabric with knit lining, high stretch
- Mid-rise waist, ruched detailing
- Drop waist seam
- Mini-length ruffled overlay, A-line fit
- Ruffled side cascading accent
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000423
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Curve Shift Striped Knit Bell Sleeve Mini Dress
This bodycon mini dress keeps the silhouette sleek with a softer finish at the neckline. The fitted shape and off-shoulder fold-over detail create a clean line, while the long bell sleeves add movement through the arms. Style it with pointed heels or knee-high boots to keep the proportions sharp.
Fit & Features
- Striped knit fabric, high stretch
- Fold-over off-the-shoulder neckline
- Long bell sleeves
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000462
Category Name: 2026 Fall Outfit Trends
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Flirty In Plaid Mesh Halter Top
Plaid just got a little more flirtatious. This mesh halter top hugs the figure with ruched sides, a plunging V-neckline, and an open back that makes the matching mini skort feel instantly more styled.
Shop Matching Bottoms: Flirty In Plaid Mesh Ruffle Mini Skort
Fit & Features
- Plaid-printed mesh fabric with knit lining, high stretch
- Sleeveless V-neckline
- Tie-back halter straps, open back
- Ruched side seams
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000814
Category Name: 2026 Fall Outfit Trends
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Checked In Plaid Funnel Neck Bomber Jacket
Plaid just found its cooler weather upgrade. This cropped bomber jacket mixes an oversized fit with a high funnel neck and relaxed sleeves for an easy throw-on layer that makes mini skirts, denim, and boots instantly styled.
Fit & Features
- Plaid pattern, woven fabric, sewn-in woven lining
- High funnel neckline with snap-button closures
- Relaxed long sleeves with snap-button cuffs
- Front zip-up closure
- Oversized fit
- Cropped bubble hem
- Runs true to size
Style Number/Barcode: 06202-000143
Category Name: 2026 Fall Outfit Trends
Price: $59.90
Availability: In Stock
Available Color: BROWN
Available Size: L
Product Badge:- Best Seller
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Chic Move Faux Leather Belted Trench Coat
Consider your outerwear officially upgraded. This faux leather trench coat brings a belted waist, relaxed long-line fit, and polished structure that make everything from dresses to denim look instantly sharper.
Fit & Features
- Faux leather fabric with woven lining, no stretch
- Lapel neckline
- Long sleeves with buttoned straps at the shoulders and hems
- Double-breasted button design, tie-front belt
- Side pockets
- Long-length hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06204-000205
Category Name: 2026 Fall Outfit Trends
Price: $79.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Pattern Crush Paisley Hanky Hem Midi Skirt
The print is doing all the talking. This paisley print midi skirt features stretchy mesh and an asymmetric hanky hem, made to pair with the matching halter top or a sleek crop top.
Shop Matching Top: Pattern Crush Paisley Cowl Neck Halter Top
Fit & Features
- Paisley-printed mesh fabric with knit lining, high stretch
- Mid-rise waist
- Midi-length asymmetric hanky hem
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-000203
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Stripe Shift Knit Midi Skirt
A striped moment that keeps the look interesting. This striped knit midi skirt features an asymmetric hem with a flowy silhouette, perfect with the matching top or paired with a cropped tee and a sleek jacket.
Shop Matching Top: Stripe Shift Knit Halter Top
Fit & Features
- Striped knit fabric with knit lining, high stretch
- Mid-rise waist
- Asymmetric drop waist seam
- Midi-length asymmetric hem
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-000204
Category Name: 2026 Fall Outfit Trends
Price: $34.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Stripe Shift Knit Halter Top
A striped moment that keeps the look interesting. This striped knit halter top hugs the figure with a plunging V-neckline and open back, perfect with the matching skirt or paired with denim and a sleek jacket.
Shop Matching Bottoms: Stripe Shift Knit Midi Skirt
Fit & Features
- Striped knit fabric with knit lining, high stretch
- Sleeveless plunging V-neckline
- Tie-back halter straps, open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000810
Category Name: 2026 Fall Outfit Trends
Price: $26.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Double Take Low-Rise Flared Capri Pants
The capri comeback is getting a sharper, more tailored update. A low-rise waist and double-button front keep the silhouette sleek through the hips, while the cropped flared leg adds a fresh twist to the throwback shape. It’s a polished take on the trend that still feels playful and current.
Fit & Features
- Smooth knit fabric, minimal stretch
- Low-rise waist, belt loops
- Extended waist tab, double-button and hidden zipper front closure
- Fitted through the hip and thigh
- Cropped flared leg
- Clean tailored finish
- Runs true to size
Style Number/Barcode: 06502-000134
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Shade Theory Rectangular Frame Sunglasses
Consider your outfit instantly more interesting. These rectangular sunglasses pair a sleek, low profile shape with softly tinted lenses and a chunky frame for that effortless cool factor made for everyday fits and weekend plans.
Fit & Features
- Plastic frame construction
- Slim rectangular silhouette
- Tinted lenses
- Wide arms with a structured finish
- Tortoiseshell pattern
Style Number/Barcode: 07008-000282
Category Name: 2026 Fall Outfit Trends
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Downtown Drift Faux Leather Moto Jacket
Consider your fall layers officially upgraded. This faux leather moto jacket brings a vintage-inspired finish, stand collar neckline, and zip front for that cool city edge that works with everyday styling.
Fit & Features
- Faux leather fabric, sewn-in woven lining
- Stand collar neckline with snap button
- Front zipper closure
- Zip front pockets
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06204-000203
Category Name: 2026 Fall Outfit Trends
Price: $64.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L, XL
Product Badge:- New Arrival
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Downtown Edge Faux Leather Bomber Jacket
Your jacket rotation just found its sleek side. This faux leather bomber jacket brings a structured edge with utility-inspired pockets, shoulder tabs, and a cropped hem that pairs effortlessly with your cold-weather outfits.
Fit & Features
- Faux leather fabric, sewn-in woven lining
- High mock neckline, snap-button shoulder strap accents
- Long sleeves with snap-button cuffs
- Hidden front zip-up and snap-button closures
- Front flap pockets
- Elasticized crop-length hem
- Runs true to size
Style Number/Barcode: 06204-000201
Category Name: 2026 Fall Outfit Trends
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL