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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Velvet Leopard Print Crop Top
Velvet and leopard print have definitely become a go-to! This crop tank is designed with adjustable spaghetti straps, a v neckline that has a lace trim, and a horizontal stitching below the cup area. Tank has a cropped hemline and is composed of a velvet material that offer moderate stretch, a form fit, and a leopard print pattern!Style Number/Barcode: 06001-2124
Category Name: Night Out
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Velvet Bodysuit
Get some fierce fashion with this leopard print velvet bodysuit! It features a sleeveless bodice, adjustable spaghetti straps, a sweetheart neckline with underwire cups, a square back with a keyhole cut out and a single button closure, flattering vertical seam detailing down the front, and a thong bottom with dual snap button closures. The velvet fabric is unlined and offers moderate stretch and a form hugging fit.Style Number/Barcode: 06001-2128
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Velvet Stripe Tie Waist Shorts
Chic and perfect for fall, these velvet stripe shorts are a must-have for any fashionista! They feature a high rise waist, a tie front belt, a hidden front zipper and button closure, hidden front pockets, and relaxed fitting shorts. The velvet fabric offers moderate stretch and are lined with a knit fabric.Style Number/Barcode: 06403-0070
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Buy Me A Drink Satin Cropped Tank
Have everyone out here buying you a drink with that style babe! We love you in satin, don't forget to pick up the matching skirt that is sold separately to complete your sweet satin attire!
Fit & Features
- Adjustable spaghetti straps
- V-neckline
- Empire style cropped hemline
- Elastic hemline only at back
- Satin
- No stretch
Style Number/Barcode: 06003-0556
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry Sequins Midi Dress
This jaw-dropping midi dress is just what you need for your holiday outings!
Fits & Features
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Adjustable Spaghetti Straps
- Sweetheart Neckline With Padded Cups
- Zipper With Hook & Eye Closure At Back
- Midi Length Silhouette
- Lined, Sheer Mesh Fabric With Diamond & Scroll Print Pattern Sequins
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0602
Category Name: Night Out
Price: $9.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps
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Romantic Ruffles Satin Mini Dress
Bring the romance with charming satin! This mini dress is a major head turner!
Fit & Features
- Asymmetrical Ruffle
- Long Sleeves | Ruffle Hem
- Wide Round Neckline
- Satin
- Mini Length Silhouette
- Form Hugging Fit | Minimal Stretch
- Hidden side zipper closure
Style Number/Barcode: 06003-0633
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mini Pearl Door Knocker Earrings
Baby all you need is a small finishing touch and these cutie little pearl door knockers are just the thing!
- Square design
- Pearl detailing
- Post back closure
Style Number/Barcode: 07001-0298
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make Me Blush Rhinestone Pointed Mule
You make us blush with that fabulous style bby! Top it all off with the cutest clear kitten mules!
- Pointed closed toe
- Rhinestone detailing
- Clear design
- Clear kitten heel
Style Number/Barcode: 07401-0760
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Embossed Snake Print Zippered Mini Skirt
Edgy and chic, this embossed snake print mini is such a must!
Fit & Features
- High rise waist
- Complete zip up front
- Zippered faux pockets
- Short, form hugging fit
- Embossed snake print
- Faux leather fabric | Minimal stretch
Style Number/Barcode: 06401-0173
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crushing On Velvet Flocked Floral Midi Dress
This floral velvet midi dress hugs in all the right places with a cutout back that keeps it sultry and a flattering bodycon silhouette that flaunts your curves, perfect for date night or dressy celebrations.
Fit & Features
- Flocked velvet floral pattern, mesh-lined fabric
- Tube neckline
- Cutout back, stretchy smocked strap
- Bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-000085
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Suede Ruched Mini Skirt
Get a chic look for the winter season with this adorable faux suede mini!
Fit & Features
- High rise waist
- Hidden back zipper closure
- Faux wrap front
- Front ruched detail
- Faux suede fabric | Woven lining
- Form hugging fit | Moderate stretch
Style Number/Barcode: 06401-0166
Category Name: Night Out
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Make A Ponte Mini Skirt
Strut right out in this curve-hugging skirt! No matter the season, it's an essential piece to all those looks you got in mind!
Shop Matching Top: Make A Ponte Fringe Crop Top
Fits & Features
- High Rise, Elastic Waistband
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Smooth Ponte Knit Fabric
- Moderate Stretch
Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06501-0239
Category Name: Night Out
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- High Rise, Elastic Waistband
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Livin' Large Rhinestone Teardrop Earrings
Live large, and make a statement when you add in these stunning rhinestone teardrop earrings! They would look so amazing with a bell sleeve dress, or a 70's style jumpsuit!
- Large teardrop design
- Four row rhinestone detailing
- Rose gold finish
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0377
Category Name: Night Out
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Side Slit Midi Skirt
Sleek & oh so chic, this side slit midi skirt will amp up your trendy look! Pair with a graphic tee and some booties.
Fit & Features
- High rise elastic banded waist
- Thigh high side slit
- Flowy, A-line fit
- Satin-like fabric with a sheen
- Minimal stretch
Style Number/Barcode: 06401-0229
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dainty Wrap Around Strap Block Heels
Keep it chic in a wrapped block heel. The block heels feature an almond toe with a single band, dainty wrap around straps, a back ankle strap and a block heel. The heels are composed of faux suede material and a faux leather footbed. Complete your night out ready look with a curve-hugging midi dress and luxe clutch.
Fit & Features
- Almond toe
- Wrap around straps
- Behind the ankle strap
- Block heel
- Faux suede material
Style Number/Barcode: 07401-2267
Category Name: Night Out
Price: $20.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romantic Gestures Rhinestone Hoop Earrings
Give your look a touch of romance when you finesse it with rose gold and rhinestones! Pair with a satin dress, or a mini skirt & bodysuit look!
- Large hoop earrings
- Rhinestone encrusted
- Rose gold
- Omega closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-0437
Category Name: Night Out
Price: $5.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Having A Moment Square Toe Black Shiny Heels
Have yourself a trendy moment when you step out in these cuties! Square toe changes your look up a bit and pairs well with mini dresses and straight leg bottoms!
- Open square toe
- Wrap around ankle strap
- Adjustable pin buckle closure
- Faux leather | Shiny patent
- Low heel
Style Number/Barcode: 07401-2297
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Rhinestone Hoops
The more rhinestones the better! Spice up a casual look with these glam hoops.
Fit & Features
- Silver Hoop Design
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0529
Category Name: Night Out
Price: $5.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stepping Up Clear Strap Mules
Step up your heel game in mules that slay! This must-have pair features an open-almond toe with a clear strap over the toe, a narrow block heel, and a faux nubuck sole. Complete look with a ribbed midi dress.
Fit & Features
- Open back
- Open-almond toe
- Clear PVC strap over the toe
- Thin block heel
- Faux nubuck sole
Style Number/Barcode: 07401-2455
Category Name: Night Out
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strut and Stun Faux Leather Block Heels
Strut it out in these chic heels that will level the right impression! The heels feature an ankle strap, a zippered back, an open almond toe, and a block heel. Complete your look with a ribbed midi dress and a blazer.
Fit & Features
- Ankle strap
- Zippered back
- Open almond toe
- Block heel
- Faux croc-embossed pattern
- Faux leather material
Style Number/Barcode: 07401-2451
Category Name: Night Out
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Suede Fishnet Ankle Stiletto Booties
Give your look a trendy vibe in these faux suede stiletto booties! They feature a pointed toe, a fishnet ankle design, and a sleek stiletto heel. Pair these chic booties with a basic mini dress for fab 'fit.
Fit & Features
- Pointed toe
- Fishnet ankle design
- Stiletto heel
- Partial faux suede material
Please be advised that these booties run 1/2 a size small.
Style Number/Barcode: 07403-0392
Category Name: Night Out
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clearly Chic Rhinestone Pointed Toe Pumps
Clearly your outfit will be oh-so-chic in these pumps! They feature a clear PVC pointed toe and closed back with rhinestone detailing, a thin adjustable ankle strap, and a sleek stiletto heel. Pair these pumps with light wash distressed denim to dress up a casual 'fit.
Fit & Features
- Clear PVC pointed toe and closed back
- Rhinestone detailing
- Thin adjustable ankle strap
- Stiletto heel
Style Number/Barcode: 07401-2516
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Moment of Luxe Rhinestone Lace-Up Heels
Create a luxe moment in heels that reflect glamour and glitz. The heels feature lace-up rhinestone and faux patent leather straps, a multi cross-strap design, an open almond toe, and a gorgeous rose gold-tone. Complete look with a LBD.
Fit & Features
- Lace-up straps
- Rhinestones
- Multi cross strap design
- Open almond toe
- Stiletto heel
- Faux patent leather material
Style Number/Barcode: 07401-2514
Category Name: Night Out
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Babe Faux Suede Block Heels
A basic block heel is a style staple that every babe needs! Perfect for dressing up with your formal outfits or chic workwear outfits, a block heel is a must! The heels feature an adjustable ankle strap with a closed-back, an open square toe with a single strap, and a sturdy block heel.
Fit & Features
- Closed-back
- Adjustable ankle strap
- Open square toe
- Single strap over the toe
- Block heel
- Faux suede material
Style Number/Barcode: 07401-2621
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale