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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Flirt in Motion Plaid Pleated Mini Skort
This mini skort blends preppy and playful with pleated plaid, lace trim, and built-in shorts that keep every move stress-free. Equal parts cute and cheeky—it’s the piece you reach for weekly.
Fit & Features
- Plaid printed knit fabric
- Wide mid-rise waistband
- Pleated overlay skirt with built-in shorts for coverage
- Scalloped lace trim
- Mini-length skort silhouette
- Runs true to size
Style Number/Barcode: 06503-000228
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Statement Season Faux Leather Trench Coat
Statement season starts here. This sleek faux leather trench coat brings a chic attitude with a perfectly structured fit—made for nights out, city strolls, and every unapologetically confident moment in between. Style with the matching mini skort.
Shop Matching Bottoms: Statement Season Faux Leather Mini Skort
Fit & Features
- Patent faux leather fabric, crinkle texture
- Lapel collar, back flap accent
- Long sleeves, strap details
- Open front, tie-front belt
- Long-length hem
- Structured fit
- Runs true to size
Style Number/Barcode: 06204-000073
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Patent faux leather fabric, crinkle texture
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Wrapped In Charm Off-Shoulder Mini Dress
This mini dress is that perfect mix of soft and sculpted—the one you reach for when you want to look undone in a chic way. The foldover off-shoulder neckline adds a flirty twist, while the rib knit hugs you with just the right amount of confidence.
Fit & Features
- Soft rib knit fabric with stretch
- Foldover off-shoulder neckline with subtle twist detail
- Fitted long sleeves
- Bodycon silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000469
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Girl Slays Buckle Denim Skort
Serving legs and attitude—this denim skort does both. The sleek mini silhouette with statement buckle details keeps it playful, while the built-in shorts make it ready for festivals, concerts, or weekend hangs.
Fit & Features
- Dark wash denim, built-in knit shorts
- Mid-rise waist, back zipper and hook-eye closure
- Faux leather studded waist trim with dual buckle accents
- Form-hugging fit
- Mini-length
- Runs true to size
Style Number/Barcode: 06603-000164
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Polished Mock Neck Mini Dress
This is the kind of dress you reach for when you want to look pulled together without overthinking it. Clean lines, a smooth ribbed fit, and a mock neck give it that quiet confidence that works day to night with a quick switch of shoes.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Mock neckline
- Long fitted sleeves
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000460
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Gloss Patent A-Line Skort
When subtle just isn’t on the schedule. This patent A-line skort serves high shine confidence with a sleek mini silhouette and built-in shorts, so you can flirt with the hemline and still feel covered from lunch dates to wine bars with the girls!
Fit & Features
- Glossy patent faux leather fabric
- Mid-rise waist
- A-line, form-hugging fit
- Mini-length hem
- Built-in shorts lining
- Runs true to size
Style Number/Barcode: 06403-000113
Category Name: 2026 Fall Outfit Trends
Price: $34.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Cool Intentions Faux Leather Pants
The cool-girl classic your closet’s been waiting for. These faux leather straight-leg pants nail that effortless balance—structured, smooth, and just the right amount of bold. Perfect with an oversized tee, a blazer, or whatever vibe you’re feeling.
Fit & Features
- Faux leather fabric, minimal stretch
- High-rise waist
- Straight-leg fit
- Front button and hidden zipper closure
- Belt loop accents, faux front pockets, open back pockets
- Runs true to size
Style Number/Barcode: 06402-000028
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Cool High-Rise Wide Leg Pants
Your “don’t mess with me” pants—sleek, sculpting, and effortlessly cool. These faux leather wide-leg pants bring major attitude with a high-rise fit that snatches the waist and elongates the leg. Dress them up, tone them down, they always deliver main character polish (without saying it).
Fit & Features
- Sleek faux leather fabric, minimal stretch
- High-rise waist
- Wide-leg fit
- Front button and hidden zipper closure
- Belt loop accents, faux front pockets, open back pockets
- Runs true to size
Style Number/Barcode: 06402-000027
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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City Cool Cropped Denim Jacket
The kind of layer that pulls everything together. This cropped denim jacket delivers that lived-in feel with a sharp, confident cut—perfect for throwing on and instantly looking styled.
Fit & Features
- Vintage-inspired structured denim fabric
- Long sleeves with button cuffs
- Classic collar with button-front closure
- Cropped silhouette
- Raw-cut hem detail
- Runs true to size
Style Number/Barcode: 06203-000028
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: BLACK, DENIM
Available Size: S, M, L, XL
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Kangol Tropic™ 504 Black Beret
Instantly raises your outfit IQ. This iconic Kangol beret adds that effortless, editorial touch. Whether you’re pairing it with a moto jacket or oversized blazer, it’s your go-to for any look this season.
Fit & Features
- "Kangol" embroidery and logo
- Tropic™ yarn for a lightweight and comfortable fit
- Classic beret silhouette
Style Number/Barcode: 07302-000229
Category Name: 2026 Fall Outfit Trends
Price: $23.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- "Kangol" embroidery and logo
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Off Duty Cool Faux Leather Jacket
The kind of layer that makes a tank and denim feel intentional. This washed moto jacket features a sleek zip front and structured seams that give you that effortless model off-duty vibe without trying too hard.
Fit & Features
- Washed faux leather fabric with woven lining, no stretch
- Moto silhouette with stand collar neckline
- Front zip closure with snap button details
- Long sleeves with tailored seam detailing, single button details
- Cropped length hem
- Runs true to size
Style Number/Barcode: 06204-000107
Category Name: 2026 Fall Outfit Trends
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off Duty Cool Faux Leather Zip Up Bomber
The layer you throw on when the outfit already hits—but needs attitude. This faux leather bomber brings that effortless, pulled-together edge that works day to night without overthinking it.
Fit & Features
- Smooth faux leather fabric
- Classic bomber silhouette with relaxed structure
- Collared neckline for a clean finish
- Long sleeves with elasticized cuffs
- Front pockets
- Front zipper closure with elasticized hem
- Runs true to size
Style Number/Barcode: 06204-000106
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Chic Off-The-Shoulder Top
The kind of off-the-shoulder top that low-key steals the whole outfit without even trying. The ribbed knit hugs just right, and the sleek grommet trim gives you that effortless chic vibe.
Fit & Features
- Ribbed knit fabric, high stretch
- Off-the-shoulder straight-across neckline
- Front grommet trim
- Long fitted sleeves
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000468
Category Name: 2026 Fall Outfit Trends
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Majorly Chic Ribbed Knit Mock Neck Midi Dress
Meet the midi dress that makes minimal feel major. The mock neck and keyhole detail bring a chic vibe, while the ribbed knit stretch keeps it comfy enough from brunch meet-ups to dinner dates.
Fit & Features
- Ribbed hacci knit fabric with knit lining, high stretch
- Sleeveless mock neckline
- Keyhole cutout at the bust
- Angled seams under the bust
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000422
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kangol Tropic™ 504 Beige Beret
Instantly raises your outfit IQ. This iconic Kangol beret adds that effortless, editorial touch. Whether you’re pairing it with a moto jacket or oversized blazer, it’s your go-to for any look this season.
Fit & Features
- "Kangol" embroidery and logo
- Tropic™ yarn for a lightweight and comfortable fit
- Classic beret silhouette
Style Number/Barcode: 07302-000230
Category Name: 2026 Fall Outfit Trends
Price: $4.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- "Kangol" embroidery and logo
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City Check Houndstooth Plaid Crop Jacket
Classic, but make it cool. This cropped wool-blend jacket gives total it-girl energy with its houndstooth plaid print, structured collar, and retro-inspired silhouette. Perfect for layering over outfits when the fit needs a little polish.
Fit & Features
- Houndstooth plaid print
- Wool-blend fabric, sewn-in woven lining
- Collar neckline
- Long sleeves with button strap cuffs
- Button-down front closures
- Faux front pockets, crop-length hem
- Runs true to size
Style Number/Barcode: 06201-000081
Category Name: 2026 Fall Outfit Trends
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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City Drift Oversized Jacket
Cool-girl comfort meets vintage soul. This oversized jacket gives that perfectly worn-in feel with coated fabric, quilted lining, and a cozy corduroy collar. Toss it over flowy dresses or denim jeans for an effortless vibe this season.
Fit & Features
- Coated, vintage-inspired, cotton-blend woven fabric
- Quilted woven lining
- Long sleeves, snap-button straps
- Corduroy collar neckline
- Front zipper and snap-button closures, front flap pockets
- Oversized fit
Style Number/Barcode: 06201-000083
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy And Captivating Bodycon Mini Dress
All eyes on you. This off-the-shoulder ribbed mini dress hugs every curve in soft, stretchy knit with a foldover neckline that adds just the right amount of flirt. The long sleeves balance the bodycon fit for a look that’s equal parts cozy and captivating.
Fit & Features
- Soft rib knit stretch fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000405
Category Name: 2026 Fall Outfit Trends
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep Them Curious Tie Back Mini Dress
This dress keeps it minimal from the front and magnetic from the back—the open cut and tie detail gives just enough drama while the rib knit smooths everything into place. It’s an easy yes for plans when simple feels the sexiest.
Fit & Features
- Rib knit fabric with subtle texture
- Boat neckline with long fitted sleeves and flared cuffs
- Bodycon silhouette through the bodice and skirt
- Open back design with wide band and tie-back closure
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000402
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Girl Pinstripe Button Top
Office-core but make it flirty. This pinstriped button-down top skims the body with a sculpted fit and subtle flyaway front, giving polished energy with just the right amount of edge for day-to-night styling.
Fit & Features
- Pinstriped pattern, woven top
- Long sleeves
- Collar neckline
- Dual button front closure, center split
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000252
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Wild Confidence Zebra Print Mesh Tie-Front Top
Serving wild confidence with zero effort. This zebra print mesh tie-front top features a plunging neckline and flowy, flyaway fit that moves with you from late-night plans to spontaneous weekend styling.
Fit & Features
- Mesh fabric with ruffled trim, high stretch
- Zebra print
- Plunging V-neckline
- Tie-front detail, flyaway design
- Long bell sleeves
- Mid-length flowy hem
- Runs true to size
Style Number/Barcode: 06202-000074
Category Name: 2026 Fall Outfit Trends
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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Can’t Resist Off-The-Shoulder Mini Dress
A little cozy, a little flirty—this rib knit mini dress does both. Designed with a foldover off-the-shoulder neckline, ruched sides, and a soft front drape that flatters every curve, it’s your go-to for coffee dates, casual dinners, or weekend chic plans.
Fit & Features
- Soft rib knit fabric lined with stretch knit
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Side ruched seams
- Front drape accent, bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000396
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Snug Cable Knit Mini Dress
Cozy meets curve-hugging. This cable knit mini brings that soft, flirty energy with a foldover off-the-shoulder neckline and bell sleeves for extra charm. Perfect for date nights in or dressing up your coffee run fit.
Fit & Features
- Soft cable knit fabric, stretch knit lining
- Foldover off-the-shoulder neckline
- Long bell sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000395
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid About You Vest Top
A little preppy, a little flirty—this plaid vest top does both. Perfect for dressing up or keeping it casual, it’s your go-to for effortless styling.
Shop Matching Bottoms: Plaid About You Mini Skort
Fit & Features
- Woven fabric with knit lining, moderate stretch
- Plaid print
- Sleeveless scoop neckline
- Tank shoulder straps
- Button-down front
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06202-000048
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free