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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After Hours Poplin Long Sleeve Top
This poplin top takes a tailored silhouette and opens it up—literally—with sleek hardware closures and a clean center cutout that feels modern, confident, and just a little rebellious. Pair it with trouser pants, mini skirts, or denim jeans and watch how effortlessly it sharpens your look
Fit & Features
- Poplin woven fabric
- Classic collar neckline
- Center cutout with dual metallic hardware closures
- Darted bodice for subtle shape
- Hip-skimming length hem
- Runs true to size
Style Number/Barcode: 06003-000233
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Flirt Mode Faux Leather Skort
Equal parts fierce and flirty. This faux leather skort serves attitude with a ruffled tiered design and a short, flattering fit—your go-to for a concert or a bold day look.
Fit & Features
- Sleek faux leather fabric, stretchy knit shorts lining
- High-rise waist
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 06501-000093
Category Name: 2026 Fall Outfit Trends
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: M, L
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City Cutie Denim Lace Up Skort
This denim skort gives you the best of both worlds — a flirty mini vibe in the front with the comfort and confidence of shorts in the back. The lace-up placket adds that little edge that makes even a simple outfit feel styled.
Fit & Features
- Denim fabric, slight stretch
- Mid-rise waist, back zipper and hook-eye closure
- Lace-up placket at front
- Skort front with shorts backing
- Structured yet comfy fit
- Runs true to size
Style Number/Barcode: 06603-000129
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Stroll Ruched Midi Skirt
This peasant midi skirt features side drawstring ruching that lets you adjust the vibe—wear it low-key relaxed or ruched up for extra shape.
Fit & Features
- Cotton-blend woven fabric
- Mid-rise elasticized waist
- Adjustable side ruched drawstrings
- Relaxed silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06301-000009
Category Name: 2026 Fall Outfit Trends
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fall for Knit Long Sleeve Mini Dress
Cozy, flattering, and totally fall-coded. This ribbed knit mini dress features a sweetheart neckline and subtle ruching that shapes your silhouette while keeping it soft and effortless. Pair it with knee-high boots for a perfect fall day out.
Fit & Features
- Hacci rib knit stretch fabric
- Sweetheart neckline, ruched bust seam
- Fitted long sleeves
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000354
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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City Stroll Straight Leg Jeans
These straight-leg jeans bring that effortlessly polished off-duty vibe that makes every sidewalk feel like your runway. The structured denim and clean silhouette keep your look sharp from brunch to golden hour hangs.
Fit & Features
- Structured denim fabric
- Mid-rise waist
- Straight leg silhouette
- Classic five-pocket design
- Runs true to size
Style Number/Barcode: 06602-000081
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: 1, 3, 5, 7, 9, 11, 13
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Spotted Muse Leopard Wide-Leg Jeans
These leopard-spot flares bring that fierce, effortless confidence that works whether you’re dressing up or keeping it casual. The structured rise meets a flowy leg for a look that always lands—no overthinking required.
Shop Matching Corset: Spotted Muse Leopard Cropped Corset
Fit & Features
- Mid-rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Leopard pattern
- Denim fabrication
- Flared wide-leg hem
- Runs true to size
Style Number/Barcode: 06602-000082
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild At Heart Lace Leopard A-Line Mini Dress
Turn up the heat in this sultry leopard mini dress. The fierce leopard print, lace bust, and flared skirt make it the perfect mix of wild and romantic. Whether it’s a night out or a wine bar evening, this dress brings all the allure.
Fit & Features
- Leopard print, mesh fabric, stretchy knit lining
- Lace bust sweetheart neckline, underwire cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000353
Category Name: 2026 Fall Outfit Trends
Price: $18.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Remix Striped Flare Pants
Retro flair meets everyday comfort. These striped flare pants sculpt your shape with a soft stretch fit that’s equal parts chill and elevated—perfect for coffee runs, office hours, or casual nights out.
Fit & Features
- Striped print, stretch knit fabric
- Smooth high-rise waist
- Hip-hugging fit
- Flared hem
- Runs true to size
Style Number/Barcode: 06502-000063
Category Name: 2026 Fall Outfit Trends
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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City Slick Coated Mid Rise Capri Pants
Polished with a little edge—these coated capris were made for that cool-girl off-duty vibe. The sleek finish gives denim an upgrade, while the cropped cut keeps it fresh for day-to-night styling.
Fit & Features
- Coated woven fabric, slight stretch
- Mid-rise waist
- Back zipper closure
- Form-hugging fit
- Side slit accents
- Capri-length fit
- Runs true to size
Style Number/Barcode: 06402-000016
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off-The-Shoulder Moments Slit Maxi Dress
This off-the-shoulder maxi dress features ruched details that contour your shape, plus a high side slit for effortless allure. Perfect for shower celebrations, formal dinners, or anytime you want all eyes on you.
Fit & Features
- Smooth knit stretchy fabric
- Folded off-the-shoulder neckline
- Fitted long sleeves
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000344
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Too Cool Studded Denim Jeans
Edge up your everyday style in these denim jeans. Boasting curve-contouring studded embellishments and a trendy flared hem, these jeans will be your new go-to for day or night plans.
Fit & Features
- Denim fabric, color fade effect
- High-rise waist
- Hip-hugging fit
- Flared hem
- Studded side embellishments
- Front button closure, pockets, belt loops
- Runs true to size
Style Number/Barcode: 06602-000080
Category Name: 2026 Fall Outfit Trends
Price: $24.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Agenda Pleated Skort
This faux leather pleated skort comes with a statement belt and a mini silhouette that says main character without even trying. Pair it with a trendy knit sweater for instant outfit chemistry.
Fit & Features
- Faux leather fabric, shorts lining
- High-rise waist
- Back zipper closure
- Belted accent
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000087
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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Rosé All Day Lace Up Heels
Bloom into the spotlight—these lace-up heels feature chic wraparound straps and a bold floral accent that makes every step a statement. Perfect for brunch, weekend trips, or any dressed-up moments.
Fit & Features
- Stiletto heel
- Square toe
- Crochet rose on toe strap
- Lace-up ankle straps
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000574
Category Name: 2026 Fall Outfit Trends
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Minimal Drama Off-The-Shoulder Midi Dress
Simple, sleek, and seriously flattering. This foldover off-the-shoulder midi dress hugs every curve with a soft stretch fit—perfect for dinner plans, date nights, or any moment that calls for subtle confidence.
Fit & Features
- Brushed knit fabric, smooth stretchy knit lining
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000340
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kangol Faux Fur Trim Trapper Hat
Level up your cold-weather vibe with this Kangol trapper hat that’s all about cozy meets cool. The faux fur trim keeps it luxe, while the Kangol embroidery adds that signature touch.
Fit & Features
- Wool-blend material
- Plush faux fur trim
- Round top
- Ear flaps, woven ties
- Woven lined interior with padding
- "Kangol" back embroidery and logo
- Runs true to size
Style Number/Barcode: 07302-000204
Category Name: 2026 Fall Outfit Trends
Price: $41.97 $84.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Wool-blend material
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Kangol Corduroy Bucket Hat
Low-key iconic—this Kangol corduroy bucket hat gives your outfit that instant cool factor without even trying. The classic Kangol logo keeps it timeless, while the texture adds just the right amount of edge.
Fit & Features
- Corduroy material
- Internal cotton seams
- "Kangol" front embroidery and logo
- Classic bucket shape
- Runs true to size
Style Number/Barcode: 07302-000205
Category Name: 2026 Fall Outfit Trends
Price: $4.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kangol Zebra Print Faux Fur Bucket Hat
Go bold or go home—this Kangol bucket hat takes cozy to a whole new level. The zebra print faux fur and iconic Kangol logo make it an instant statement piece for every outfit.
Fit & Features
- Plush faux fur material with zebra print
- Satin woven lining
- "Kangol" front embroidery and logo
- Runs true to size
Style Number/Barcode: 07302-000207
Category Name: 2026 Fall Outfit Trends
Price: $4.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kangol Faux Fur Shearling Bucket Hat
Street style just leveled up—this Kangol shearling bucket hat is equal parts cozy and iconic. With its plush faux fur and signature Kangol logo, it’s the ultimate finishing touch for chill days or statement 'fits.
Fit & Features
- Faux fur shearling material
- Side trims
- Fleece-lined flap
- Knit lining
- "Kangol" front embroidery and logo
- Runs true to size
Style Number/Barcode: 07302-000203
Category Name: 2026 Fall Outfit Trends
Price: $4.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kangol Multi Faux Fur Trapper Hat
Cold weather but make it cute—this Kangol faux fur trapper hat is the cozy upgrade your winter 'fits deserve. The plush texture and ear flaps keep you warm while the Kangol tag finishes it with signature flair.
Fit & Features
- Plush multi-color faux fur material
- Oversized crown
- Ear flaps, woven ties
- Woven lined interior with padding
- Small Kangol logo tag
- Runs true to size
Style Number/Barcode: 07302-000206
Category Name: 2026 Fall Outfit Trends
Price: $41.97 $84.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Refined Chic Ribbed Midi Dress
Simple, sleek, and seriously versatile. This ribbed midi dress nails that effortlessly polished vibe with a body-hugging fit and mock neckline. Style with gold hoops and slides for brunch—or heels and a blazer for a polished look for a business lunch.
Fit & Features
- Soft rib knit stretch fabric, knit lining
- Sleeveless mock neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000337
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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Effortless Cutie Off-The-Shoulder Mini Dress
Your “cute but effortless” mini dress has entered the chat. The off-the-shoulder neckline and body-hugging ribbed knit bring soft confidence with a flirty edge—made for everything from coffee dates to late-night plans.
Fit & Features
- Ribbed knit fabric, high stretch
- Sweetheart neckline, knot accent at the bust
- Off-the-shoulder design
- Long fitted sleeves
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000334
Category Name: 2026 Fall Outfit Trends
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Mood Faux Suede Baseball Cap
Your new off-duty essential. This faux suede baseball cap elevates any casual vibe with its soft texture and minimalist finish—making it the perfect hat to top off your look for weekend plans and coffee runs.
Fit & Features
- Classic baseball cap silhouette
- Curved wide brim
- Adjustable back strap for a snug fit
- Soft faux suede material
Style Number/Barcode: 07302-000198
Category Name: 2026 Fall Outfit Trends
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Slow Morning Club Baseball Cap
For the girl who runs on iced lattes and vibes. This Slow Morning Club embroidered baseball cap is the laid-back staple you’ll reach for on repeat.
Fit & Features
- Classic baseball cap silhouette
- Structured curved brim
- Slow Morning Club embroidered detail
- Velcro back strap
- Two-tone design
Style Number/Barcode: 07302-000194
Category Name: 2026 Fall Outfit Trends
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free