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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Autumn Edit Plaid Cabby Cap
A little vintage, very fall ready. This plaid cabby cap mixes a softly structured crown with a contrast faux suede brim and buckle detail for the kind of finishing touch that makes denim, knits, and trench coats feel instantly more styled.
Fit & Features
- Plaid cabby cap silhouette
- Contrast faux suede brim
- Side buckle accent
- Paneled crown with top button
- Structured visor
Style Number/Barcode: 07302-000401
Category Name: 2026 Fall Outfit Trends
Price: $18.90
Availability: Out of Stock
Product Badge:- Ships Free
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Stacked Intent Amber Stone Bangle Set
More bracelets, more styling options. This mixed bangle set layers braided textures, sleek metal bands, and faceted amber-toned stones for a curated stack that does the accessorizing for you.
Fit & Features
- Mixed multi-bangle set
- Braided and textured metal designs
- Faceted amber-tone stone accents
- Stackable statement styling
- Stretch fit
Style Number/Barcode: 07003-000360
Category Name: 2026 Fall Outfit Trends
Price: $15.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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City Drama Faux Fur Trench Coat
Outerwear just got a little more cinematic. This longline faux leather trench pairs plush shag trim with sleek sleeves and a sweeping silhouette for the kind of fall layer that does all the styling for you.
Fit & Features
- Faux leather fabric, plush faux fur trim, sewn-in lining
- Open front with oversized faux fur collar
- Hidden front hook and eye closure
- Long sleeves with faux fur cuffs
- Longline trench silhouette
- Side pockets
- Runs true to size
Style Number/Barcode: 06204-000202
Category Name: 2026 Fall Outfit Trends
Price: $89.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Checks in Motion Plaid Chiffon Poncho
Plaid just got sheer. This chiffon poncho brings an airy style to bandeaus, tank tops, and denim bottoms for an effortless fall layer with a little drama.
Fit & Features
- Sheer plaid chiffon fabric
- Crew neckline with back keyhole with button closure
- Draped poncho silhouette with open sides
- Asymmetrical flowing hem
- Runs true to size
Style Number/Barcode: 06204-000199
Category Name: 2026 Fall Outfit Trends
Price: $24.90
Availability: In Stock
Available Color: SAGE
Available Size: XS/S, M/L
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City Limits Faux Leather Cabby Hat
For coffee runs, crosswalk struts, and plans that somehow turn into three stops. This faux leather cabby hat gives your city uniform a polished edge with a sleek, structured shape, curved brim, and buckle detail.
Fit & Features
- Classic cabby hat silhouette
- Curved structured brim
- Buckle strap detail with hardware trim
- Lined interior
- Smooth faux leather material
Style Number/Barcode: 07302-000400
Category Name: 2026 Fall Outfit Trends
Price: $18.90
Availability: Out of Stock
Product Badge:- Ships Free
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Check Mate Plaid Draped Asymmetrical Skirt
Classic plaid, reworked for now. This asymmetrical skirt pairs a low-rise waist with draped construction and an uneven hem for a more fashion-forward fall look.
Shop Matching Top: Check Mate Cropped Plaid Tube Top
Fit & Features
- Plaid print, knit fabric
- Low-rise waist
- Draped asymmetric flowy silhouette
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000202
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Check Mate Cropped Plaid Tube Top
Fall plaid, but with better details. This cropped tube top uses a scarf accent to give the strapless neckline a trendy flair while the fitted silhouette flaunts your figure.
Shop Matching Bottoms: Check Mate Plaid Draped Asymmetrical Skirt
Fit & Features
- Plaid print, knit fabric
- Strapless neckline with scarf included
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000807
Category Name: 2026 Fall Outfit Trends
Price: $32.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Fall Routine Faux Suede Utility Jacket
Your layering lineup just found its new favorite. This faux suede jacket mixes a relaxed cropped shape with oversized utility pockets and a zip front for an easy autumn style that still feels polished.
Fit & Features
- Vintage-inspired faux suede fabric, sewn-in woven lining
- Collared neckline, front zip-up closure
- Long sleeves with snap-button cuffs
- Front flap pockets with snap closures
- Elasticized hem with snap-button strap accent
- Runs true to size
Style Number/Barcode: 06204-000200
Category Name: 2026 Fall Outfit Trends
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Night Shift Lace-Up Faux Leather Flare Pants
The lace-up front gives these pants its sharpest point of difference. These faux leather flare pants combine grommet detailing with a sleek finish and flared leg for a bold, streamlined look. The hardware keeps the attitude dialed in.
Fit & Features
- Faux leather fabrication
- Low-rise waist
- Front lace-up detail with metal grommets
- Flared silhouette
- Runs true to size
Style Number/Barcode: 06402-000055
Category Name: 2026 Fall Outfit Trends
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Chalet Mood Faux Fur Denim Skirt
Denim just booked a cozy weekend away. This mini skirt mixes classic denim with an oversized faux fur trim and bodycon fit for a plush fall layer that makes even the simplest outfit feel styled.
Shop The Matching Jacket: Chalet Mood Faux Fur Denim Jacket
Fit & Features
- Denim fabric, sewn-in knit lining
- Mid-rise waist
- Bodycon silhouette
- Faux fur trim mini-length hem
- Front button closure
- Runs true to size
Style Number/Barcode: 06601-000040
Category Name: 2026 Fall Outfit Trends
Price: $42.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Laced In City Lace Up Cabby Hat
Your hat lineup just got a little sharper. This structured cabby hat features a paneled crown, curved brim, and lace up grommet detailing along the side for an edgy finish that makes everyday layers feel more styled.
Fit & Features
- Structured paneled crown
- Curved brim
- Side lace up grommet detailing
- Classic cabby silhouette
- Runs true to size
Style Number/Barcode: 07302-000399
Category Name: 2026 Fall Outfit Trends
Price: $18.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Chalet Mood Faux Fur Denim Jacket
Denim just booked a cozy weekend away. This cropped jacket mixes classic denim with an oversized faux fur collar and matching cuffs for a plush fall layer that makes even the simplest outfit feel styled.
Shop The Matching Skirt: Chalet Mood Faux Fur Denim Skirt
Fit & Features
- Denim fabric, sewn-in knit lining
- Oversized faux fur collar
- Long sleeves with faux fur cuffs
- Cropped silhouette with front snap-button closure
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06203-000069
Category Name: 2026 Fall Outfit Trends
Price: $64.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Off Duty Edit Cabby Hat
Consider your off-duty look officially upgraded. This cabby cap brings a tailored finish to oversized coats, fitted knits, and everything you’re wearing on repeat this season.
Fit & Features
- Soft fabrication blend
- Paneled newsboy silhouette
- Short structured brim
- Slip-on design
- Runs true to size
Style Number/Barcode: 07302-000402
Category Name: 2026 Fall Outfit Trends
Price: $19.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Waist Game Lace Up Faux Leather Belt
Your outfit just found its eye-catching finishing touch. This faux leather belt brings lace-up detailing, metal hardware, and a statement buckle to dresses, oversized tops, and layered looks.
Fit & Features
- Wide structured silhouette
- Lace-up front design
- Adjustable buckle closure
- Faux leather material
Style Number/Barcode: 07301-000522
Category Name: 2026 Fall Outfit Trends
Price: $19.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Dainty Plaid Bow-Front Mini Skort
Plaid gets a softer finish with one simple detail. This mini skort features a neat bow at the front waist, adding contrast to the structured pattern and close-to-the-body shape. The result feels polished, playful, and easy to work into your rotation.
Fit & Features
- Knit fabric
- Plaid flannel pattern
- High-rise fit, bow detail at front waist
- Side zipper and hook-eye closure
- Mini-length overlay, form-hugging fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000418
Category Name: 2026 Fall Outfit Trends
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Best Seller
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Fringe Appeal Tassel Earrings
Your jewelry lineup just found its playful side. Sculptural metal accents, glossy bead details, and swishy tassels bring drama to your everyday and dressy looks.
Fit & Features
- Sculptural metal accents
- Glossy beading
- Fringe tassel design
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000565
Category Name: 2026 Fall Outfit Trends
Price: $12.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: NS
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Fold Over Twill Envelope Mini Skort
Fall styling is leaning into cleaner lines. This envelope mini skort pairs a structured twill finish with an asymmetrical front for a more directional take on the season’s mini trend. Add a fitted sweater and knee-high boots to keep the look polished.
Fit & Features
- Woven twill fabric
- High-rise fit
- Asymmetrical envelope front design
- Form-hugging fit
- Back zipper closure
- Back pocket accents
- Runs true to size
Style Number/Barcode: 06303-000070
Category Name: 2026 Fall Outfit Trends
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Wrapped Up Sculpted Drop Earrings
A little drama, beautifully framed. These statement drop earrings pair glossy dimensional stones with sculpted metal detailing for an artful finish that instantly dresses up sleek tops and special occasion looks.
Fit & Features
- Statement drop earring design
- Glossy dimensional stone accents
- Sculpted metal framing
- Graduated three-drop silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000560
Category Name: 2026 Fall Outfit Trends
Price: $12.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: NS
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Gallery Drop Sculpted Stone Earrings
Consider these the art piece of your jewelry lineup. These statement drop earrings pair glossy oval stones with sculpted metal frames for a polished finish that makes simple necklines feel instantly more elevated.
Fit & Features
- Statement drop earring design
- Glossy oval stone accents
- Sculpted metal framing
- Double drop silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000564
Category Name: 2026 Fall Outfit Trends
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Poised Step Polka Dot Bow Mules
Polished, playful, and ready for plans. These satin mules pair a refined polka dot print with an oversized bow and stiletto heel for an elevated finish with midi dresses, denim outfits, and mini skirts.
Fit & Features
- 3" stiletto heel
- Almond toe
- Wide strap with bow
- Cushioned insole
- Polka dot pattern
- Satin material
- Runs true to size
Style Number/Barcode: 07401-000882
Category Name: 2026 Fall Outfit Trends
Price: $28.90
Availability: In Stock
Available Color: BROWN
Available Size: 5.5, 6, 6.5
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Cross My Mind Gemstone Stackable Ring Set
Your ring stack just found its bolder side. This five-piece ring set mixes faceted gemstone accents, sleek bands, and cross details so you can pile them on together or split them up depending on the outfit.
Fit & Features
- Five-piece stackable ring set
- Faceted gemstone accents
- Cross motif details
- Mixed band designs
- Wear together or separately
Style Number/Barcode: 07004-000158
Category Name: 2026 Fall Outfit Trends
Price: $14.90
Availability: In Stock
Available Color: EMERALD
Available Size: 7, 8
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Triple Trouble Rhinestone Layered Necklace
A little edge, neatly layered. This three-strand necklace mixes delicate chains, faceted rhinestone accents, and graduated drop details for a sleek stacked look that instantly sharpens plunging necklines and going-out 'fits.
Fit & Features
- Three-strand layered necklace
- Faceted rhinestone accents
- Graduated drop details
- Delicate chain construction
- Adjustable lobster clasp closure with extender
Style Number/Barcode: 07002-000698
Category Name: 2026 Fall Outfit Trends
Price: $14.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Chain Reaction Tassel Pendant Necklace
A little movement makes all the difference. This long pendant necklace pairs a sleek chain with sculpted link accents and a fluid chain tassel for an easy statement that instantly pulls the outfit together.
Fit & Features
- Long chain necklace design
- Sculpted link pendant detail
- Draped chain tassel accent
- Lobster clasp closure with extender
Style Number/Barcode: 07002-000696
Category Name: 2026 Fall Outfit Trends
Price: $16.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Fresh Pick Floral Pendant Necklace And Earrings Set
Florals, but with a polished little upgrade. This matching jewelry set pairs a delicate flower pendant necklace with coordinating drop earrings for an easy way to make your accessories feel fully styled.
Fit & Features
- Metal construction
- Two-piece necklace and earrings set
- Sculpted floral pendant and matching flower charms
- Delicate chain with lobster clasp and fish hook earrings
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07002-000695
Category Name: 2026 Fall Outfit Trends
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS