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.
Now Trending
STYLE SPOTLIGHT
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.
-
Plans Optional Striped Dolman Top
Consider your outfit plans handled. This striped dolman top brings an effortlessly draped, off-shoulder fit that works from casual hangs to plans that somehow turned into drinks.
Fit & Features
- Soft stretch knit fabrication
- Wide boat neckline with off-shoulder styling
- Relaxed dolman sleeves with elbow-length coverage
- Striped pattern
- Draped silhouette with a cropped hem
- Runs true to size
Style Number/Barcode: 06002-000687
Category Name: 2026 Fall Outfit Trends
Price: $26.90
Availability: In Stock
Available Color: BLUE
Available Size: M
-
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: S, M, L
-
Checked Out Plaid Capri Pants
Retro called, but we’re keeping these. These plaid capri pants bring a close fit, cropped length, and a tiny bow detail that makes baby tees, fitted tanks, and kitten heels feel instantly more styled.
Fit & Features
- Plaid woven fabrication
- Low-rise waist with bow detail
- Slim fit through the hips and legs
- Cropped capri length with side hem slits
- Runs true to size
Style Number/Barcode: 06502-000127
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: L
-
All Fastened Button Up Wide-Leg Jeans
The buttons are doing more than closing the deal. These wide-leg jeans feature a full-length placket that adds a bold vertical detail to the classic denim shape. Style with a cute top and heels.
Fit & Features
- Denim material
- Mid-rise waist
- Front button-up detailing
- Classic five-pocket styling, belt loop accents
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06602-000127
Category Name: 2026 Fall Outfit Trends
Price: $59.90
Availability: In Stock
Available Color: MEDIUM, DENIM
Available Size: 1, 3, 5, 7, 9, 11, 13
-
Command Attention Military Denim Jacket
This cropped denim jacket brings a structured, military-inspired edge with statement button tabs and a sleek zip front that layers effortlessly over your favorite looks this season.
Fit & Features
- Cotton-blend denim fabric, moderate stretch
- Standing collar neckline
- Front zip-up closure
- Long sleeves with dual button cuff detailing
- Military-inspired button tabs
- Crop-length hem, fitted silhouette
- Runs true to size
Style Number/Barcode: 06203-000066
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: S, XL
Product Badge:- Best Seller
-
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
-
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
-
Double Take Open-Back Top
Chic in front, plot twist in back. This open-back top keeps the front sleek with a boat neckline and cap sleeves, then flips the script with a draped back that makes even simple bottoms feel way more considered.
Fit & Features
- Smooth and stretchy knit fabric
- Boat neckline
- Short cap sleeve
- Draped open back
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06002-000683
Category Name: 2026 Fall Outfit Trends
Price: $24.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
-
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: S, M, L
-
Effortless Look Knit Poncho
Fit & Features
- Knit fabric, moderate stretch
- Off-shoulder boat neckline
- Flowy fit
- Asymmetric hem
- Runs true to size
Style Number/Barcode: 06005-000438
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS/S, M/L
-
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
-
Everyday Upgrade Wide-Leg Jeans
The pair your closet was waiting for. These wide-leg jeans sit at the mid-rise with an easy full-length silhouette and washed finish that makes everything from fitted tops to barely-there heels feel instantly more styled.
Fit & Features
- Denim fabric, washed finish
- Mid-rise waist
- Five-pocket and belt loop design
- Front button and hidden zipper closure
- Wide-leg silhouette, relaxed fit
- Runs true to size
Style Number/Barcode: 06602-000131
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
-
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
-
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: S, M, L
Product Badge:- Part of a Set
-
Checked In Gingham Jacket
Consider this your shortcut to looking styled without overthinking it. The gingham jacket pairs a high funnel neckline with a relaxed zip-front shape for that sporty meets polished vibe that works way beyond the matching set.
Shop Matching Shorts: Checked In Gingham Hot Shorts
Fit & Features
- Gingham pattern, cotton woven fabric and sewn-in lining
- High funnel neckline with snap-button closures
- Front hidden zipper closure
- Long sleeves with snap-button cuffs
- Side pockets. relaxed silhouette
- Adjustable drawstring hem with toggles
- Runs true to size
Style Number/Barcode: 06204-000188
Category Name: 2026 Fall Outfit Trends
Price: $59.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Best Seller
-
Checked In Gingham Hot Shorts
Consider this your shortcut to looking styled without overthinking it. These gingham shorts keep things short, sleek, and very intentional. Designed with a high-rise fit and close silhouette, they pair perfectly with the matching jacket and look just as good styled solo with a fitted tank or baby tee.
Shop Matching Jacket: Checked In Gingham Jacket
Fit & Features
- Woven gingham fabric
- High-rise waist
- Side button tab details
- Cheeky fit
- Runs true to size
Style Number/Barcode: 06303-000068
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Best Seller
-
Spotted Out Polka Dot Halter Top
Polka dots just made the guest list. This halter top pairs a plunging V-neckline with a sleek cropped fit for a flirty throwback look that still feels completely current.
Shop Matching Capri Pants: Spotted Out Polka Dot Capri Pants
Fit & Features
- Stretch polka dot fabric
- Halter neckline with plunging V front
- Contoured bust seams with subtle side ruching
- Fitted cropped silhouette
- Runs true to size
Style Number/Barcode: 06001-000799
Category Name: 2026 Fall Outfit Trends
Price: $29.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
-
Pattern Crush Floral Plaid Halter Top
Plaid with a seriously pretty plot twist. This floral flocked halter top mixes sheer mesh texture, velvet florals, and a deep V-neckline for a fitted look that feels dressed up without going overboard.
Fit & Features
- Plaid printed mesh fabric with knit lining, high stretch
- Velvet flocked floral pattern
- Sleeveless deep V-neckline, ruched bust
- Tie-back halter straps, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000786
Category Name: 2026 Fall Outfit Trends
Price: $29.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
-
Reservations Pending Denim Mules
Your jeans are officially jealous. Denim-textured straps meet sleek contrast trim for a heeled sandal that makes even the simplest going-out look feel considered.
Fit & Features
- 3" Kitten heel
- Denim-textured upper with contrast trim
- Open-toe silhouette
- Knotted strappy front design
- Luxe fit cushioned insole
- Slip-on heeled construction
- Runs true to size
Style Number/Barcode: 07401-000755
Category Name: 2026 Fall Outfit Trends
Price: $30.90
Availability: In Stock
Available Color: BROWN
Available Size: 5, 5.5, 6.5, 7.5, 8, 8.5, 10
-
Pool Hall Crush Suede Bubble Bomber Jacket
Your going-out jacket just got dangerously good. This suede bubble bomber jacket brings an oversized shape, cropped hem, and lived-in finish that makes every basic underneath look instantly cooler.
Fit & Features
- Suede-look fabrication with a lived-in finish, sewn-in woven lining
- Stand collar with snap tab detailing
- Zip front closure with relaxed drop shoulders
- Cropped bubble silhouette with adjustable drawcord hem
- Runs true to size
Style Number/Barcode: 06204-000170
Category Name: 2026 Fall Outfit Trends
Price: $56.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Undeniable Flair Halter Corset Top
Add that undeniable flair to your look with this faux leather corset top! Featuring a plunging halter neckline for a daring look, a lace-up back for the perfect fit, and a crop hem for a trendy touch.
Fit & Features
- Faux leather fabric, sewn-in knit lining
- Halter plunge neckline with tie straps
- Bungee spaghetti strap lace-up back
- Underwire bust
- Flexible boning
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-000138
Category Name: 2026 Fall Outfit Trends
Price: $29.90
Availability: In Stock
Available Color: BLACK, BURGUNDY, RED
Available Size: XS, S, M, L
Product Badge:- Sale
-
Worth Staying Out For Studded Faux Leather Corset Top
Your going out top just entered the chat. This faux leather corset top brings a strapless sweetheart neckline, studded detailing, and a sculpted fit that makes denim feel instantly more dressed up.
Fit & Features
- Faux leather fabrication
- Strapless sweetheart neckline
- Studded trim along neckline
- Structured corset seams
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-000450
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, M, L
-
Guest List Strappy Kitten Heels
The pair that makes every dress feel instantly more polished. Slim crossover straps, a toe loop, and a sculpted kitten heel give these sandals that chic look with just enough statement.
Fit & Features
- 3" Kitten heel
- Square toe
- Strappy thong design
- Adjustable ankle strap with buckle closure
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000736
Category Name: 2026 Fall Outfit Trends
Price: $30.90
Availability: Out of Stock
Product Badge:- Ships Free
-
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