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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Always A Sensation High-Rise Ponte Skort
Where ever the party is, this high-rise ponte skort is ready to make a stylish entrance! Designed with a form-hugging fit and high-rise waist leading to the faux wrap front skirt overlay adding a chic touch while the shorts lining provides extra coverage. Complete the look in a basic tank top.
Fit & Features
- Ponte fabric, moderate stretch
- High-rise waist
- Faux wrap skirt overlay
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06503-1165
Category Name: Night Out
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fliratious Beauty Floral Mini Dress
Bring your flirty style to your date night look in this gorgeous satin floral mini dress! It features a sleeveless cowl neckline, spaghetti straps, an open back with a lace-up strappy design, and a short, curve-hugging, bodycon silhouette. Complete the look with sleek hoop earrings.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Open back, cross-back, lace-up strappy design, tie closure
- Mini-length hem, form-fitting silhouette
- Smooth satin-knit fabric, moderate stretch
- All-over floral print
- Runs true to size
Style Number/Barcode: 05101-1722
Category Name: Night Out
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Melanie Formal Sequin Midi Dress
Special Occasion
Bring the sparkle with our enchanting Melanie dress! She features a sleeveless bodice, a plunging V neckline, tank-like straps and a midi length silhouette with a high side slit. The all over sequins are set in a captivating scroll print pattern. Dress is composed of mesh knit fabric that offers a relaxed fit.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0237
Category Name: Night Out
Price: $19.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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She's a Sweetheart Velvet Mini Dress
Show off your sweet and sexy side! This dress definitely gives us holiday feels! Designed with a rhinestone trim sweetheart neckline, spaghetti straps that are adjustable, padded cups, and a curve flattering form fit. Dress is composed of a velvet like fabric that offers moderate stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0188
Category Name: Night Out
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Lover Bodysuit
We've all become a lover of leopard print, it's the new neutral! Pair this adorable bodysuit with your fave pair of denim.
Fit & Features
- Long fitted sleeves
- Wrap front creating a V neckline
- High waist seam
- Thong bottom | Dual snap button closures
- Brushed knit fabric
- Plenty of stretch
Style Number/Barcode: 06001-2411
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On-Trend Lucite Block Heels
Stay on-trend with heels that show how on-trend you are! The heels feature an open back with an adjustable ankle strap, a square toe with a clear strap over the toe, and a clear lucite block heel. Complete look with a disty floral dress and a charm necklace.
Fit & Features
- Open back with adjustable ankle strap
- Open square toe with
- Clear PVC strap over the toe
- Lucite block heel
- Faux leather material
Style Number/Barcode: 07401-2683
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beautifully Beaded Cropped Bustier
Elevate your night-out look with this beautifully beaded cropped bustier! It features a sleeveless bodice, adjustable spaghetti straps, lined molded cups, and an intricate sequin and beaded front design. Complete the outfit with high-rise denim and new heels.
Fit & Features
- Adjustable spaghetti straps
- Lined molded cups, underwire, flexible boning
- Sequin and beaded front design
- Sheer woven fabric
- Cropped, form-hugging fit
- Runs true to size
Style Number/Barcode: 06003-1221
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Sparkle Cutout Glitter Bodycon Mini Dress
Flaunt your glam sparkle in this glitter mini dress boasting a sexy cutout back and bodycon silhouette that flaunts your curves!
Fit & Features
- Glitter knit fabric lined with stretchy knit
- Sweetheart neckline, padded bra cups
- Wide shoulder straps
- Cutout back with strap and hook closure
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-6101
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Showstopping Strappy Stiletto Heels
Get an alluring on-trend look in these showstopping stilettos! They feature an open almond-shaped toe, a thick strappy design with buckle detailing, and a sleek stiletto heel. Pair these shoes with a chic clutch.
Fit & Features
- Open almond-shaped toe
- Thick strappy design
- Adjustable ankle straps, buckle details
- Stiletto heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3313
Category Name: Night Out
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Don't Stop Faux Leather Croc Embossed Block Heels
Don't stop the party vibes in this pair of croc-embossed faux leather heels! They feature a croc-embossed design, block heel, and an open toe. They're pure perfection with a crop top and distressed denim for an on-trend look.
Fit & Features
- Open toe
- Block heel
- Croc-embossed design
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3460
Category Name: Night Out
Price: $7.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edgy Appeal Faux Leather Coated Skinny Pants
Bring major edgy appeal with pants that dare to go bold. The pants feature a mid-rise waist, dual vertical seams on the legs, an exposed side zipper closure with mini O-Ring, and a skinny leg fit. The pants are composed of a coated stretchy knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a graphic tee and combat boots.
Fit & Features
- Mid-rise waist
- Dual vertical seams on the legs
- Exposed side zipper closure
- Skinny leg fit
- Coated knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06402-0408
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Vibe Alert Faux Suede Booties
Bring those chic vibes with booties that dress up your casual outfits! The booties feature an around the ankle fit, an inner zipper closure, elastic goring accent, a pointed toe, and a block heel. The booties are composed of a faux suede material. Complete look with plaid coat and skinny jeans.
Fit & Features
- Around the ankle fit
- Inner zipper closure
- Elastic goring accent
- Pointed toe
- Block heel
- Faux suede material
- Runs true to size
Style Number/Barcode: 07403-1459
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitz Bae Rhine Fishnet Faux Leather Skirt
If you love the glitz and glamorous things, this faux leather mini skirt is just the ticket! It features a sleek high-rise waist, a bodycon silhouette, and a front slit with rhinestone fishnet trim. Complete the look in a chic satin top for drinks with the girls!
Fit & Features
- High-rise waist
- Back zipper closure
- Bodycon silhouette
- Front slit with rhinestone fishnet trim
- Mini-length hem
- Faux leather fabric
- Runs true to size
Style Number/Barcode: 06401-0487
Category Name: Night Out
Price: $11.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Party Lights Sequins Wrap Skirt
Radiate the party lights when you show up in this mini sequin skirt featuring a high-rise waist, bodycon silhouette, and wrap hem with a slit accent. The sequin knit fabric offers plenty of stretch. Style with a sparkly bustier to complete the look!
Fit & Features
- High-rise elasticized waist
- Bodycon silhouette
- Wrap mini-length hem
- Slit accent
- Sequin knit fabric, plenty of stretch
- Fits true to size
Style Number/Barcode: 06501-0800
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Fearless Rhinestone Corset Top
Feeling fearless with fashion? This rhinestone corset top is sure to elevate your outfit! It features a square neckline, wide shoulder straps, flexible boning for structure, and a cropped hem on lined metallic fabric. Complete the look in statement denim jeans for an evening out!
Fit & Features
- Sleeveless square neckline
- Wide shoulder straps
- Back zipper and hook-eye closure
- Flexible boning, cropped hem
- Rhinestone embellished
- Metallic fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-2265
Category Name: Night Out
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Edgy Attitude Faux Leather Under-The-Knee Boots
These chic faux leather under-the-knee boots will give your outfits an edgy attitude you'll love. They feature an under-the-knee design with asymmetric stitching and trendy studded accents, buckle straps at the ankle, an inner zipper closure for easy on-and-off styling, a round-shaped toe, and a tall block heel. Style with a mini dress and an oversized blazer!
Fit & Features
- Under-the-knee design, pull tabs
- Asymmetric stitching, studded accents
- Buckle straps at the ankle
- Inner zipper closure
- Round toe, tall block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0968
Category Name: Night Out
Price: $9.97 $58.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check Me Out Lace Trim Plaid Crop Top
Catch all the attention in this plaid crop top perfect for any occasion! With delicate lace shoulder straps and a V-neckline and trim, this top offers a subtle romantic vibe and a fitted crop hem to style with high-rise bottoms.
Fit & Features
- Plaid print, mesh fabric, sewn-in knit lining
- Lace shoulder straps and V-neckline
- Lace trim
- Fitted crop silhouette
- Runs true to size
Style Number/Barcode: 06001-5417
Category Name: Night Out
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Social Sweetheart Butterfly Rhinestone Spiral Heels
Get ready to spread your wings and soar to every event on your radar in these faux leather block heels to make a statement! They feature a sleek round toe with rhinestone embellished toe straps with delicate butterflies, a short block heel, a luxe fit cushion insole for ultimate comfort, and rhinestone embellished spiral ankle straps with butterflies. Complete the look with a glitzy clutch.
Fit & Features
- 2.5" Block heel
- Faux leather material
- Round toe
- Rhinestone embellished toe straps with butterflies
- Rhinestone embellished spiral ankle strap with butterflies
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4938
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylishly Sleek Faux Leather Mini Skirt
This stylishly sleek faux leather mini skirt will elevate your looks to an edgy-chic vibe! It features a high-rise waist, a faux wrap-front silhouette with ruched detailing, an asymmetric mini-length hem, and a curve-hugging fit. Pair this smooth faux leather skirt with a corset top and heels for your next night out.
Fit & Features
- High-rise waist
- Back zipper closure
- Faux wrap-front silhouette, ruching
- Asymmetric mini-length hem
- Curve-hugging fit
- Faux leather fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06401-0554
Category Name: Night Out
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bring It On Bodysuit
Bring on the sultry vibes with this fierce snake print bodysuit! It features a sleeveless bodice, a V neckline and back, thin shoulder straps, and a partial coverage bottom with snap button closures. The garment is composed of a knit 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: 06001-1265
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hypnotize Me Crop Top
Leave everyone in a trance with this stylish crop top! It features a sleeveless bodice, tank-like shoulder straps, a wrap front, and a cropped hem. The top is composed of a smooth knit fabric that offers plenty of stretch.
Style Number/Barcode: 06001-1492
Category Name: Night Out
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Open Back Caged Jumpsuit
Make a sophisticated impression in this sleek jumpsuit! It features a sleeveless bodice, a plunging V neckline, a multi strap caged bodice, adjustable spaghetti straps and a bold open back. The slim fit bodice leads to a pair of flowy wide leg pants with flared hem. Jumpsuit is composed of a lined semi-sheer chiffon fabric that offers a relaxed fit with a minimal stretch.
Style Number/Barcode: 06302-0051
Category Name: Night Out
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Deadly Yet Sexy Crop Top
Deadly never looked so sexy. This crop has a round neckline, spaghetti straps, a knot detail at the center, and a cropped hem that meets at the rib area. The crop is composed of a soft knit material that offers moderate stretch, and show cases a brushed print that will have them lookin out for danger. Don't forget the matching midi skirt!
Model is 5'6.5" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-1622
Category Name: Night Out
Price: $8.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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City Lights Buckle Heel Mules
Meet the heels that do it all—these buckle strap mules bring sleek shine with a modern square toe that’s made for night-outs, rooftop drinks, and every spotlight moment in between.
Fit & Features
- 3.5" wide stiletto heel
- Square toe
- Buckled strap
- Cushioned insole
- Patent faux leather material
- Runs true to size
Style Number/Barcode: 07401-000164
Category Name: Night Out
Price: $30.90
Availability: Out of Stock
Product Badge:- Sale