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 Move Faux Leather Straight-Leg Pants
These straight-leg pants make polished styling feel easy. Pair the sleek coated faux leather finish with a fitted knit and pointed heels for a sharper look, or add an oversized jacket to play up the contrast. The mid-rise waist and clean full-length shape keep the outfit streamlined.
Fit & Features
- Smooth coated faux leather fabric
- Mid-rise waist
- Belt loops
- Front button and zipper closure
- Front and back pockets
- Straight-leg full-length silhouette
- Runs true to size
Style Number/Barcode: 06402-000043
Category Name: 2026 Fall Outfit Trends
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, 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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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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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: S, M, L, XL
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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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Sweet Flirt Lace Ruffle Tie-Front Top
Sweetness with an edge. This lace ruffle tie-front top brings a sheer, flirty feel with a V-neckline and draped front that makes denim look instantly more planned.
Fit & Features
- Sheer lace fabric, high stretch, bust knit lining
- Short sleeves
- V-neckline, tie-front design
- Ruffled trim
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06202-000127
Category Name: 2026 Fall Outfit Trends
Price: $26.90
Availability: In Stock
Available Color: BLACK, BROWN, IVORY
Available Size: XS, S, M, L
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Preppy Pinstripe Lace Trim Skater Mini Dress
This mini dress balances crisp detail with a softer finish. Pinstripes sharpen the look, while lace trim, front buttons, and a halter tie bring contrast through the bodice. The tiered skirt keeps the overall feel playful and light.
Fit & Features
- Pinstripe pattern
- Lace trim
- Button-front bodice
- Halter tie neckline
- Tiered skater mini silhouette
- Runs true to size
Style Number/Barcode: 05103-001109
Category Name: 2026 Fall Outfit Trends
Price: $52.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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Trendy Vibe Mid-Rise Flare Jeans
Your denim lineup just found its new fave pair. These mid-rise flare jeans balance a close fit through the hips with a dramatic leg and an extended tab waist for a trendy vibe.
Fit & Features
- Denim fabric
- Mid-rise waist
- Extended tab design, button closure
- Front and back pockets
- Flared-leg silhouette
- Runs true to size
Style Number/Barcode: 06602-000135
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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City Side Chic Microsuede Buckle Band Cabby Hat
A little downtown polish goes a long way. This microsuede cabby hat brings a structured silhouette and buckle band detail that instantly sharpens jackets, knits, and off-duty looks.
Fit & Features
- Soft microsuede construction
- Structured cabby hat silhouette
- Paneled crown with covered top button
- Faux leather buckle band detail
Style Number/Barcode: 07302-000354
Category Name: 2026 Fall Outfit Trends
Price: $16.90
Availability: Out of Stock
Product Badge:- Ships Free
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Dialed In Denim Mini Skort
Denim just tightened the dress code. This high-rise mini skort features fold-over pockets and a short fitted overlay with hidden shorts for a going-out 'fit that stays dialed in. Pair with the matching corset top.
Shop Matching Top: Dialed In Denim Lace-Up Corset Top
Fit & Features
- Denim fabric
- High-rise waist, belt loops
- Dual front button closure
- Fold-over front pockets
- Mini-length overlay, fitted silhouette
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06603-000228
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: S, M, L
Product Badge:- Part of a Set
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Rebel Routine Button Detail Denim Tube Top
Denim just entered its after-dark era. This strapless tube top shapes the figure with structured seaming, statement button accents, and a front zip made for doubling down with the matching shorts.
Fit & Features
- Structured cotton-blend denim fabric, moderate stretch
- Strapless tube neckline, elasticized back
- Button accents and front zipper closure
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06003-000422
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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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: XS, S, M, L
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Buckle Up Plaid Hot Shorts
The prep trend is taking a bolder turn. These plaid hot shorts combine a low-rise shape with a matching wide belt and metal grommets for a more directional finish. Add a fitted tee or sleek top to keep the look current.
Fit & Features
- Plaid woven fabric
- Low-rise waist
- Wide matching grommet belt with buckle
- Hot-short silhouette
- Runs true to size
Style Number/Barcode: 06403-000178
Category Name: 2026 Fall Outfit Trends
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Polished Ease Cap Sleeve Mesh Maxi Dress
Consider the dressed-up plans handled. This mesh maxi dress pairs a high neckline and cap sleeves with soft ruching, keeping the look polished without feeling too formal. Wear it for wedding celebrations, cocktail parties, or birthday dinners.
Fit & Features
- High neckline with cap sleeves
- Mesh fabrication, smooth lining
- Ruched detailing through the body
- Softly gathered maxi skirt
- Body-skimming fit
- Runs true to size
Style Number/Barcode: 05101-001412
Category Name: 2026 Fall Outfit Trends
Price: $52.90
Availability: Out of Stock
Product Badge:- Ships Free
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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
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Denim Outline Mid Rise Wide-Leg Jeans
Dark-wash denim is taking on a more structured shape this season. These mid-rise jeans pair a wide leg with dual button waist detailing and front seams that sharpen the silhouette. Style with a crop top and sandals for weekend plans.
Fit & Features
- Dark wash denim fabric
- Mid-rise waist
- Dual front button closures
- Front pockets, belt loop accents
- Front leg seaming
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06602-000133
Category Name: 2026 Fall Outfit Trends
Price: $54.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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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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Sleek Attitude Pleated Faux Leather Mini Skort
Pleats with a little attitude built in. This faux leather mini skort brings a glossy finish, drop waist belt detail, and hidden shorts for the kind of look that can actually keep up.
Fit & Features
- Patent faux leather fabric
- Mid-rise waist
- Drop waist belted design, buckle detail
- Pleated mini-length overlay, front slit, A-line fit
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06403-000176
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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Plaid Attitude Mid-Rise Hot Shorts
Classic plaid with more attitude. These plaid hot shorts offer a mid-rise waist and curve-hugging fit for styling solo or matching back to the set.
Shop Matching Top: Plaid Attitude Collared Zip-Up Vest
Fit & Features
- Plaid woven fabric
- Mid-rise waist, belt loops
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06403-000180
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Rev It Up Graphic Denim Moto Jacket
Denim just hit the fast lane. This cropped moto jacket mixes racing-inspired graphics, patch details, and contrast panels with sleek zip accents for a bold layer that makes basics feel anything but basic.
Fit & Features
- Structured denim fabrication
- Cropped moto jacket silhouette
- Long sleeves with strap detailing
- Standing collar neckline with snap-button closure
- Graphic panels, patches, and zip accents
- Front zip-up closure
- Runs true to size
Style Number/Barcode: 06203-000061
Category Name: 2026 Fall Outfit Trends
Price: $59.90
Availability: In Stock
Available Color: DENIM
Available Size: S, M, L, XL
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Zip Into It Mock Neck Denim Jacket
Denim just got a sportier remix. This crop denim jacket pairs a mock neckline with a zip front and adjustable drawstring hem for that perfectly relaxed shape you can cinch your way. Style for easy layering this season.
Fit & Features
- Denim fabric, color fade effect
- Mock neckline
- Relaxed long sleeves
- Front zip-up closure
- Slouchy crop-length fit
- Adjustable drawstring crop hem
- Runs true to size
Style Number/Barcode: 06203-000059
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Laced In Lace Up Flare Denim Jeans
The flare is back, and this version brings extra edge. These denim flare jeans combine a fitted upper leg with lace-up grommet detailing and vertical seaming for a fresh take on the throwback silhouette.
Shop The Matching Jacket: Laced In Long Sleeve Lace Up Denim Jacket
Fit & Features
- Denim fabric
- Mid-rise waist
- Hip-hugging fit
- Flared leg
- Lace-up front detail with grommets
- Vertical seaming
- Runs true to size
Style Number/Barcode: 06602-000132
Category Name: 2026 Fall Outfit Trends
Price: $54.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Contrast Code Knit Waist Wide-Leg Jeans
Contrast waistbands are giving wide-leg denim a trendy upgrade. These jeans pair a mid-rise rib knit waistband with angled panel seams that bring structure and dimension to the relaxed shape. Add a crop top and sandals for everyday styling.
Fit & Features
- Medium wash denim fabric
- Contrast rib knit mid-rise waistband
- Angled paneled seaming
- Back pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06602-000130
Category Name: 2026 Fall Outfit Trends
Price: $54.90
Availability: In Stock
Available Color: MED, DENIM
Available Size: S, M, L
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City Mode Faux Leather Bomber Jacket
Built for the outfit rotation, not the back of the closet. This cropped faux leather bomber brings a boxy streetwear shape, high neck, and adjustable hem that plays just as well with minis as it does with baggy denim.
Fit & Features
- Faux leather fabric, smooth lining
- Cropped boxy bomber silhouette
- High mock neckline with zip front closure
- Adjustable drawstring hem and snap button cuffs
- Runs true to size
Style Number/Barcode: 06204-000169
Category Name: 2026 Fall Outfit Trends
Price: $69.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L