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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Butterfly Mystique Rhinestone Spiral Heels
Add a whimsical mystique to your outfit with these statement metallic block heels perfect for dressy events! They feature an almond toe, a wide toe strap with mini rhinestone trim, and a spiral ankle rhinestone strap with butterflies. Complete the look with a ring set.
Fit & Features
- Almond toe
- Wide toe strap, mini rhinestone trim
- Spiral ankle rhinestone strap with butterflies
- Block heel
- Metallic material
- Runs true to size
Style Number/Barcode: 07401-4289
Category Name: Night Out
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love For Lace Skater Dress
Showcase your undeniable love for lace with this alluring skater dress! It features a sheer lace top, long fitted sleeves, a sweetheart neckline with lined cups, a back zipper and hook and eye closure, and a crepe skirt with a high waist seam and a flirty, flowy fit. The dress offers moderate stretch.Style Number/Barcode: 05101-0248
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chiffon Smocked Off The Shoulder Top
Lightweight and airy, this stylish smocked top can be dressed up or down. It features an off the shoulder square neckline with a merrow edge trim, long billowy sleeves with smocked cuffs, and a mid-length ruffle hem. The chiffon fabric offers moderate stretch and a form hugging fit.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0382
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Party Ready Peplum Sequin Top
Get ready for an on point party look with this peplum sequin top! You'll dazzle the night away on that dance floor!
Fit & Features
- Adjustable spaghetti straps
- Sweetheat neckline | Bust stitching
- Back zipper | Hook and eye closure
- Mid-length peplum hem
- Knit fabric | Sequin embroidery
Style Number/Barcode: 06003-0447
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Double O Ring Baguette Rhinestone Belt
Bring the shine with a belt that reflects glamour! The belt features a faux leather material and a double O-ring buckle adorned with baguette-cut rhinestones. Complete look with high rise jeans.
Fit & Features
- Faux leather material
- Double O ring buckle
- Baguette-cut rhinestones
Style Number/Barcode: 07301-0224
Category Name: Night Out
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rhinestone Queen Ankle Wrap Stiletto Heels
Showcase some major style like the fashion queen you are in these dazzling heels! They feature a pointed toe with a thong strap, a rhinestone adorned ankle wrap design with a tie closure, and a stiletto heel. Pair these shoes with high rise mom jeans and a cute crop top to add some glam to your everyday look.
Fit & Features
- Pointed toe with a thong strap
- Rhinestone adorned ankle wrap design with tie closure
- Open back
- Stiletto heel
- Faux microsuede material
Please be advised that these heels run 1/2 a size small.
Style Number/Barcode: 07401-2547
Category Name: Night Out
Price: $16.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Side Tube Cutout Mini Dress
For nights when subtle just isn’t the vibe—this strapless cutout mini brings the drama with bold print, an asymmetrical hem, and that perfect hoop detail. Designed to own the dance floor.
Fit & Features
- Mixed print design, mesh fabric lined with knit
- Tube neckline
- Side cutout with hoop accent
- Bodycon fit
- Ruched mini skirt with asymmetrical hem
- Runs true to size
Style Number/Barcode: 05103-000408
Category Name: Night Out
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Slay In Style Snake Print Block Heels
Slay your look with heels that bring the style! The heels feature an adjustable ankle strap, a multi-hued snake print, an open almond toe with a strap over the toe, a block heel, and composed of faux leather material. Complete look with a LBD.
Fit & Features
- Closed-back
- Adjustable ankle strap
- Open almond toe, strap over the toe
- Block heel
- Faux leather material
Style Number/Barcode: 07401-2954
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Impression Cutout Snake Jumpsuit
Make a major impression with a jumpsuit that showcases your stunning style! The jumpsuit features a snake print, an off-the-shoulder neckline, a cutout at the midriff, and straight-styled pants. Complete your look with clear mules and hoops.
Fit & Features
- Snake print
- Off the shoulder neckline
- Cutout at the midriff
- Straight-styled pants
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0804
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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You've Got Mail Chain Halter Top
Knock, knock you've got chic! Create a sultry vibe in this chainmail halter top featuring an on-trend sleeveless, cowl neckline, a cropped hem that leads to an alluring open-back with a chain-link with lobster clasp closure. Finish your club night look in sleek faux leather pants.
Fit & Features
- Sleeveless, cowl halter neckline
- Cropped hem
- Open-back, chain-link, lobster clasp closure
- Metal material
- Runs true to size
Style Number/Barcode: 06003-1733
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Trendy Marble Print Bodysuit
You're always on top of the latest trends! Create the cutest 'fits with this marble print bodysuit. It features an off-the-shoulder sweetheart neckline, a padded bust, long fitted sleeves, and a form-hugging fit. The sheer mesh fabric features all-over flocked velvet in a marble swirl design. Style with a faux leather mini skirt and mules.
Fit & Features
- Off-the-shoulder sweetheart neckline, padded bust
- Long fitted sleeves
- Thong bottom, dual snap-button closure
- Form-hugging fit
- Sheer mesh fabric, lined bust, moderate stretch
- Flocked velvet, marble swirl design
- Runs true to size
Style Number/Barcode: 06001-4463
Category Name: Night Out
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glitzy Details Rhinestone PU Mini Skirt
If you're here for the glitz, this faux leather mini skirt is the ticket! It features a high-rise waist, front button and hidden zipper closure, four-pocket styling, belt loop accents, and front rhinestone insets. Complete the look in platform heels.
Fit & Features
- High-rise waist
- Front button and hidden zipper closure
- Four-pocket styling, belt loop accents
- Front rhinestone insets
- Form-hugging, mini-length hem
- Faux leather lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0744
Category Name: Night Out
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Knit Your Average Sweater Dress
Level up in this curve-flaunting sweater dress featuring a sleeveless, scoop neckline, spaghetti straps, a bodycon silhouette, and a mini-length hem on ribbed knit fabric with plenty of stretch. Complete the look in a crop cardigan and booties.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, scoop neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ribbed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1450
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Sleeveless, scoop neckline
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Inner Glamour Satin Ruffle Mini Dress
Unleash your inner glamour with this satin mini dress! It features a square neckline, spaghetti straps, an accent ruffle sash, a bodycon silhouette, and a mini-length hem - designed to flatter any figure and make a statement. Complete the look with an embellished clutch for a night out!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruffle sash
- Bodycon silhouette, mini-length hem
- Silky satin fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-5286
Category Name: Night Out
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Painted In Beauty High Rise Abstract Mini Skirt
Paint yourself in this beautiful one-of-a-kind mini skirt! Featuring a flattering high-rise waist, adjustable side ruched drawstrings so you customize the style, and a bodycon fit. The mini-length hem and abstract print add a touch of unique style, while the mesh fabric adds a trendy touch. Complete the look with the matching top.
Shop Matching Top: Painted In Beauty Strapless Abstract Bustier
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Abstract print
- High-rise waist
- Adjustable side ruched drawstrings
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06501-0960
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Remarkable Show-Stopper Rhinestone Mesh Mini Dress
This dazzling mini dress is designed to be a show-stopper on your next GNO! Crafted from a sheer mesh fabric embellished with countless rhinestones, this sleeveless dress brings the glamour. It features a cowl neckline, shoulder straps, and a sultry bodycon silhouette. Complete the look in stiletto heels.
Fit & Features
- Sheer mesh fabric, rhinestone embellishments
- Cowl neckline
- Shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5613
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce Look Animal Print Mesh Halter Mini Dress
Show off a fierce allure in this airy mesh mini dress designed with an abstract animal print that will turn heads. It features a sleeveless draped cowl neckline, a halter strap design with sleek O-ring accents, and a short bodycon silhouette to highlight your gorgeous curves.
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Abstract animal print
- Asymmetric cowl neckline
- Halter strap design, metal O-ring accents
- Partially open back
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05103-5964
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace Be Sheer Bustier Bodysuit
Give your outfit the perfect amount of sheer! This bustier bodysuit will instantly dress up your favorite bottoms. It features a sleeveless sweetheart neck, built-in padded cups, wide lace shoulder straps, and a sheer lace fitted bodice. Complete the look in dressy trouser pants for cocktail hour!
Fit & Features
- Sleeveless sweetheart neck
- Built-in padded cups
- Wide lace shoulder straps
- Sheer lace fitted bodice
- Fits true to size
Style Number/Barcode: 06001-4668
Category Name: Night Out
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Date Night Cutout Knit Bodysuit
This alluring cutout knit bodysuit is perf for casual date nights with your special someone. It features a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap, ruching down the sides, an asymmetric waist cutout to showcase some skin, a thong-cut bottom, and a form-hugging fit. Style with relaxed-fitting boyfriend jeans and cute mules.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Single spaghetti strap
- Side ruching
- Asymmetric waist cutout
- Thong-cut bottom, form-hugging fit
- Knit fabric, top lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4807
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Etched Western Chain Belt
This trendy floral etched western chain belt will stylishly elevate your basic 'fits. It features geometric accents with a floral etched pattern connected by a chain-link design. Includes a front clasp closure. Pair with a fitted bodysuit and faux leather pants.
Fit & Features
- Geometric accents
- Floral etched pattern
- Chain-link design
- Front clasp closure
Style Number/Barcode: 07301-0666
Category Name: Night Out
Price: $8.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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We're Still Cool Mini Skirt
Looking cool, girl! This mini slips on and features an elegant drape and flattering ruching at hips. Made of fully lined jersey knit with plenty of stretch, it pairs perfectly with the matching tank for a hot 'fit!
Style Number/Barcode: 06501-0074
Category Name: Night Out
Price: $4.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glow With It Glitter Mini Dress
Get with the glow of this glitzy glitter mini! The dress features a sleeveless bodice, spaghetti straps that lead to a cross back, a wrap front V neckline, padded cups, a high waist seam, ruched side detailing, and a short, curve hugging fit. The lined glitter knit fabric offers plenty of stretch.Style Number/Barcode: 05103-0395
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Make My Heart Flutter Velvet Jumpsuit
Your style makes our heart flutter! Designed with a deep V neckline, ruffled sleeves and a form fitting bodice, this jumpsuit shows those curves in all the right ways! Bodice leads down to a tapered form fitting skinny leg. Jumpsuit is composed of a velvet material that offers moderate stretch and is fully lined.
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06502-0173
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Sleek Square Toe Kitten Heels
A little sass, a little sleek—these heels bring it all. With square toes, dual straps, and edgy hardware trim, they’re your low-key glam upgrade for outfits that need a subtle, chic look.
Fit & Features
- 2.5" Kitten heel
- Square toe
- Dual strap design with square hardware trim
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000543
Category Name: Night Out
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free