Night Out
Plans after dark call for outfits that know how to show up. This edit of going out outfits is built for rooftop bars, concerts, birthday celebrations, and spontaneous nights that start with one drink and end somewhere unexpected. Expect curve-hugging mini dresses, statement separates, and matching sets designed to mix, match, and move with you. Cowl necklines, strapless tops, and halter silhouettes bring just the right amount of edge, while sparkly crop tops and bustiers pair effortlessly with faux leather minis or relaxed cargo pants. Finish the look with a sleek moto jacket or bomber — because a good night out always deserves a great outfit.
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Going-Out Outfits for Every Fall & Winter Plan
Windsor’s Going-Out Outfits make getting ready feel effortless, whether the plan is dinner and drinks, a bar night with friends, a date, party, or night at the club. Find curve-hugging minis, statement separates, matching sets, denim, and sexy outfits with bold details that instantly turn up your look. From laid-back nights to full-glam entrances, these night-out outfits make it easy to dress for the vibe while creating a look that feels completely your own.
What Should I Wear for a Night Out?
Start with the mood and where you're headed. For dinner or date night, try a cowl-neck or halter top with embellished jeans or a denim skort for an elevated look that doesn't feel overdone. When drinks turn into dancing, strapless tops, plunging necklines, hardware details, and open-back silhouettes bring more after-dark energy. Explore going-out tops designed to mix, match, and move with you from the first stop to the last.
For an instant outfit, going-out dresses take the guesswork out of getting ready. Bodycon minis, curve-hugging silhouettes, bold prints, and romper dresses with flirty ruffle skirts give you one-and-done options that still make a statement.
Want the whole look with even less styling? Matching sets make getting ready easy, from sparkling coordinates that bring instant party energy to trending denim sets with vests for more laid-back plans. Wear the pieces together for effortless impact, then remix them with other going-out favorites. Discover more matching sets for going-out plans when you want an instantly coordinated look.
What Going-Out Outfits Are Trending in Fall 2026?
Fall going-out style mixes seasonal color and statement denim with silhouettes that still show some skin. Try embellished jeans with a backless top for drinks, a trending denim set for a harvest event, or an asymmetrical mini with boots for a night downtown. Jorts, boleros, bold prints, and unexpected separates also give you more ways to experiment with your look, especially when Halloween plans call for an outfit that can become part of a costume or make a statement all on its own.
For Friendsgiving dinner, pair a halter or cowl-neck top with statement denim for a look that feels dressed up without going full party glam. For bar nights or weekend hangs, balance standout style with an outfit that fits the setting. Get inspired by what to wear to a bar for outfit ideas that work for everything from casual drinks to a livelier night out.
What Should I Wear for a Winter Night Out?
For a winter night out, build your look with pieces that bring the heat while giving you more coverage as temperatures drop. Try a long-sleeve mini or bodycon dress with knee-high boots, or pair a statement top and embellished denim with a faux fur jacket for dinner, drinks, or a night downtown. Gloves and chic layering pieces add extra warmth while keeping the finished outfit polished.
For holiday parties and club nights, turn up the glam with sparkle, plunging or open-back details, sleek boots, and long-sleeve styles that balance the season with after-dark appeal. Heading into New Year’s Eve? Explore Fierce and Sexy Clubwear for bold looks made for celebrating long after midnight.
Find a Going-Out Look That Feels Like You
The best going-out look fits your plans without losing your personality. Keep things casual with denim and a statement top, make getting dressed easy with a matching set, or go all-out in a mini that puts the focus on you. Windsor’s Going-Out Outfits give you the pieces to mix, match, experiment, and create a look for every mood—from laid-back fall hangs to glamorous winter celebrations.
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Faux Leather Cargo Joggers
Keep it sleek in these trendy joggers! They feature a high rise waist, a hook fasten closure with zipper, belt loops, side pockets, cargo pockets, back pockets and a straight leg fit with elastic cuff. Joggers are composed of a faux leather fabric that offers a relaxed fit with a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06402-0059
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Faux Leather Mini Skirt
Bring the drama with this stunning mini skirt! The skirt features a high rise waist and a mini length silhouette with a side slit. The skirt is composed of a faux leather fabric that offers a form-hugging fit. Complete your look with a crop top and heels.
Fit & Features
- High rise waist
- Mini length silhouette
- Side slit
- Faux leather fabric
- Moderate stretch
- Form-hugging fit
Style Number/Barcode: 06401-0293
Category Name: Night Out
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Shimmer Glitter Knit Mini Dress
Show off a gorgeous shimmer in this alluring glitter knit mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, front and back vertical center seams with ruched detailing, and a short, curve-hugging silhouette. Style this dress with rhinestone heels.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Front and back vertical center seams, ruching
- Mini-length, form-fitting, bodycon silhouette
- Glitter knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4398
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picture This Faux Fur Crop Jacket
Can't you picture yourself in this faux fur crop jacket? Elevate your outfit layering on this fab coat featuring long sleeves, a standing collar neckline with dual snap-button closures, a hidden front zipper, side pockets, and an illusion stripe design. Complete the look in lace-up heels.
Fit & Features
- Long sleeves
- Standing collar neckline
- Dual snap-button closures
- Hidden front zipper, side pockets
- Cropped hem
- Illusion stripe design, faux fur fabric
- Fits true to size
Style Number/Barcode: 06201-0294
Category Name: Night Out
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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In The Wild Leopard Ruffled Skort
Look fierce in the wild styling this leopard mesh skort! It showcases a flattering high-rise waist that leads to the tiered ruffled mini-length hem perfect for styling with heels or boots.
Fit & Features
- Leopard print, mesh-lined fabric
- High-rise waist
- Tiered ruffled mini-length hem
- Shorts lining
- Runs true to size
Style Number/Barcode: 06503-1269
Category Name: Night Out
Price: $26.90
Availability: In Stock
Available Color: LEOPARD
Available Size: XS, S, M
Product Badge:- Back In Stock
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Eyes On Polka Dot Mesh Corset Top
All eyes are on you in this polka dot mesh corset top perfect for pre-holiday festivities! It features long sleeves, a square neckline, flexible boning inserts, and a cropped hem. Complete the look in jeans and knee-high boots.
Fit & Features
- Long sleeves
- Square neckline
- Flexible boning inserts
- Cropped hem
- Polka dot mesh fabric, lined
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4343
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Alluring Dream V-Neck Lace Rosette Crop Top
You'll captivate everyone in this alluring lace crop top for an effortless dreamy look at dinner! With a sexy V-neckline and delicate spaghetti straps, this lace crop top features a rosette flower and fitted hem. Complete the look with the matching bottoms.
Shop Matching Bottoms: Alluring Dream High-Rise Lace Rosette Maxi Skirt
Fit & Features
- Lace fabric, sewn-in knit lining, stretchy
- V-neckline and spaghetti straps with trim
- Rosette flower
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-5283
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Top Spot Coated Faux Leather Skinny Pants
You know where all the top spots to be seen in these coated faux leather pants are! They feature a mid-rise waist, side zipper, and hook-eye closure, front exposed seam detailing along the skinny-leg design. Style with heeled mules to complete the look!
Fit & Features
- Mid-rise waist
- Side zipper and hook-eye closure
- Front exposed seam details
- Skinny-leg design
- Coated faux leather fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06402-1284
Category Name: Night Out
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Cool Wide-Leg Cargo Trouser Pants
Keep your casual 'fits cool and on-trend with these cargo trouser pants. They feature a high-rise waist, a button-front closure with a hidden zipper, large cargo-style side pockets, and a relaxed, wide-leg silhouette. The smooth woven fabric has minimal stretch. Style with a corset top and strappy mules.
Fit & Features
- High-rise waist
- Button-front closure, hidden zipper
- Large cargo-style side pockets
- Relaxed, wide-leg silhouette
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-1286
Category Name: Night Out
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Zip Up Chic Mini Dress
Zip up into this chic LBD! Perf for a casual night out with the girls when you want to feel a little dressier than jeans!
Fit & Features
- Collared
- Short sleeves
- Half zip up front
- Short, form hugging fit
- Stretchy knit fabric
Style Number/Barcode: 05102-0650
Category Name: Night Out
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Totally Fab One Shoulder Crop Top
Channel a totally fab look with a crop top that creates a major style moment! The crop top features a one-shoulder neckline, a short sleeve, an asymmetrical cutout, and a cropped hem. Complete look with high waist jeans and mules.
Fit & Features
- One-shoulder neckline
- Short sleeve
- Asymmetrical cutout
- Cropped hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3825
Category Name: Night Out
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Moments Twist Front Midi Dress
This midi dress deserves a moment of admiration! It features a sleeveless, v-neck, tank straps, a sultry twisted bust with cutout detail, and a bodycon silhouette on stretchy rib-knit fabric. Complete the look in strappy heels for date night.
Fit & Features
- Sleeveless, v-neck, tank straps
- Sultry twisted bust, cutout detail
- Bodycon silhouette
- Midi-length hem
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4610
Category Name: Night Out
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sexy Strappy Bodycon Mini Dress
Level up your club 'fits with this sexy strappy bodycon mini dress! It features a sleeveless V-neckline with a strappy caged front design at the bust, spaghetti straps, alluring waist cutouts that lead to the back, and a short, form-fitting silhouette that will hug your curves. Style with fringe earrings and embellished heels.
Fit & Features
- Sleeveless V-neckline
- Strappy caged front design at the bust
- Spaghetti straps
- Waist cutouts that lead to the back
- Mini-length hem, fitted bodycon silhouette
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4522
Category Name: Night Out
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edgy At Heart PU Front Slit Pants
Some days you want an edgy-chic vibe and these PU high-rise pants are it! They feature a front button and hidden zipper closure, belt loops, side pockets, and a skinny-leg design with front slit hems. Complete the look in a corset top for a music concert!
Fit & Features
- High-rise waist
- Front button and hidden zipper closure
- Belt loops, side pockets
- Skinny-leg design
- Front slit hems
- PU fabrication
- Fits true to size
Style Number/Barcode: 06502-2223
Category Name: Night Out
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Moment In Satin Ruche Mini Dress
Take time to admire your beauty in this chic satin mini dress before heading out to the party! The dress features puff long sleeves, a sweetheart neck with a center ruched bust seam, a bodycon silhouette, and side ruching that accentuates your curves. Style with sparkly hoop earrings and heels.
Fit & Features
- Puff long sleeves
- Square neck
- Center ruched bust seam
- Bodycon silhouette
- Side ruching, mini-length hem
- Smooth satin, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-2112
Category Name: Night Out
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adriana Velvet Rhinestone Dress With Gloves
Special Occasion
Conquer the night with Adriana party mini dress! This strapless velvet dress will set you apart with its glistening rhinestone trims and dramatic mini bodycon silhouette with a ruched seam detail and a padded bust. Its detachable velvet gloves sparkle with a matching trim of rhinestones. The mini-length dress is composed of a soft and luxurious velvet knit fabric with a stretchy knit lining. Complete the daring look with a chic choker necklace and heels for a cocktail event or fancy celebration!
Fit & Features
- Strapless neckline, rhinestone trim, padded bust
- Back zipper and hook-eye closure
- Front ruched seam, bodycon silhouette, mini-length hem
- Detached elbow-length gloves, rhinestone trim
- Luxe velvet knit fabric, stretchy knit lining
- No bra required
- Runs true to size
Style Number/Barcode: 05001-1603
Category Name: Night Out
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Strut Faux Leather Under-The-Knee Boots
Fit & Features
- 3.5" Block heel, 7" leg opening, 13" shaft height
- Faux leather material, sheen-like finish
- Under-the-knee height
- Pointy toe
- Complete inner zipper closure
- Runs true to size
Style Number/Barcode: 07402-1032
Category Name: Night Out
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charming Drama Plunge Halter Corset Top
Soft embroidery, fitted silhouette—balance, babe. With a plunge halter neckline and lace-up back, this corset bodice brings the drama and the charm to your favorite denim bottoms!
Fit & Features
- Faux suede fabric, embroidery
- Plunge halter neckline
- Hidden front hook-eye closures
- Fitted crop hem
- Partial open back, lace-up design
- Runs true to size
Style Number/Barcode: 06003-000101
Category Name: Night Out
Price: $12.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glisten And Glimmer Sequin Lace-Up Dress
Glisten and glimmer from every angle in this sequin mini dress at your next dressy celebration party! It features a sleeveless square neck, spaghetti straps that lace up in the back, and a short form-hugging silhouette. The dress is designed with a sequin-scroll pattern that adds luxe vibes! Complete the look in glitter platform heels for extra sparkle!
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Lace-up back, lower zipper and hook-eye closures
- Form-hugging silhouette, mini-length hem
- Sequin-scroll patterned fabric
- Sewn-in stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2000
Category Name: Night Out
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Fab Satin Ruched Mini Dress
You'll be feeling fab in this satin mini dress for the perfect club look! It features a sleeveless sweetheart neck with a twisted padded bust and keyhole accent, adjustable spaghetti straps, side, and back ruched seams to accentuate your curves, and a bodycon silhouette. Style with sassy platform heels.
Fit & Features
- Sleeveless sweetheart neck
- Twisted, padded bust with keyhole accent
- Adjustable spaghetti straps
- Side and back ruched seams, back zipper and hook-eye closure
- Bodycon silhouette, mini-length hem
- Lined satin fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4819
Category Name: Night Out
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Diamonds & Pearls Bodysuit
You deserve all the diamonds and pearls, so wear the life of luxury with this bodysuit! It has bustier style cups with padding, adjustable shoulder straps, a lace-covered bust decorated with sequins, beads, and pearls, a hidden side zipper closure, and a thong bottom with snap button closures. Bodysuit is partially lined and composed of a sheer mesh fabric that offers plenty of stretch.Model is 5'7 with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9249
Category Name: Night Out
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Here To Stun Lace Trim Bodycon Mini Dress
This stunning ruched mesh mini dress features a lace sweetheart neckline with a ruched draped overlay, dainty lace trim spaghetti straps, and a bodycon silhouette to hug your gorgeous curves. Style with stiletto heels for a formal date night!
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Lined lace sweetheart neckline with lace trim, padded bust
- Lace trim adjustable spaghetti straps
- Back zipper with hook-eye closure
- Ruched draped overlay, ruched side seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5827
Category Name: Night Out
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Moment Nubuck Stiletto Bootie
Create a chic moment in booties that go with everything! These must-have booties feature side cutouts at the ankle, an almond toe with a platform, and a wide stiletto heel. Complete your look with a cardigan and high waist jeans.
Fit & Features
- Ankle-length
- Side cutouts at the ankle
- Adjustable ankle strap
- Almond toe, platform
- Inner zipper closure
- Wide stiletto heel
- Faux Nubuck material
Style Number/Barcode: 07403-0321
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cross Drop Hoop Earrings
A change to your hoop game, these hoops are detailed with rhinestone crosses hanging in the center of a large hoop by a gold chain. The earrings have a stud detail with a circular rhinestone attached with four prongs and a post back closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0055
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale