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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Wild Feline Leopard & Tiger Ruched Midi Dress
Spotted: The purrrrrrfect midi dress! Shake up your look and add some animal print in your wardrobe.
Fits & Features
- Bungee Spaghetti Straps
- Elastic Square Neckline
- Ruched Design
- Mixed Leopard & Tiger Inspired Print
- Midi Length Silhouette
- Mesh Composition I Fully Lined
- Little Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0406
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Square Neck Faux Leather Mini Dress
Add some edge to your wardrobe with this faux leather mini dress! It features a sleeveless bodice, square neckline with interior no-slip strip, cord spaghetti straps, princess seaming detail, and a mini length silhouette. Composed of sleek faux leather, it offers a curve-hugging fit with a moderate amount of stretch.
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05103-0545
Category Name: Night Out
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stride In Style Strappy Jumpsuit
Stride by your squad in style in this strappy back satin jumpsuit! They'll all be asking where you got your chic look.
Fit & Features
- Cross back spaghetti straps leading to a back tie closure
- Slight cowl neckline
- Dart seam detailing
- High waist seam
- Wide pant legs
- Satin-like fabric | Moderate stretch
Style Number/Barcode: 06502-0217
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Do It With Finesse Peep Toe Stiletto Mules
Finish off your look with a touch of finesse, when you add in a pair of clearly fierce stiletto mules!
- Pointed peep toe
- Thick clear band
- Open back
- Clear lucite stiletto heel
- Hidden breathable hole detailing
Style Number/Barcode: 07401-0662
Category Name: Night Out
Price: $14.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ingrid Lurex X Front Dress
Special Occasion
Show off those shoulders and sparkle all night long in our elegant Ingrid dress! She has a body con construction and features a dramatic, draped X-front neckline, a tank-style back with zip closure, and a seamed, midi-length skirt with a small front slit.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0317
Category Name: Night Out
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Satin Leopard Print Midi Dress
Sassy and stylish, this leopard print midi was made for a fashionista like you. It features a sleeveless bodice, adjustable spaghetti straps, a cowl neck, a square back with a hidden zipper and hook and eye closure, a wrap front creating a thigh high slit, and a mid-length, flowy fit. The satin-like fabric has no stretch.Style Number/Barcode: 05101-0436
Category Name: Night Out
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Zebra Print Midi Dress
You love to make a bold fashion statement, and this zebra print midi will not disappoint! It features a sleeveless bodice, adjustable spaghetti straps, a cowl neck, a square back with a hidden zipper and hook and eye closure, a wrap front with a slit, and a mid-length, flowy fit. The satin-like fabric has no stretch.
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0435
Category Name: Night Out
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Mesh Bodysuit
Sheer mesh fabric and trendy snake print give this bodysuit a sultry stylish vibe.
Fit & Features
- Long fitted sleeves
- Wrap front | Plunging V neckline
- High waist seam
- Thong bottom | Dual snap button closures
- Sheer mesh top | Knit bottom
- Plenty of stretch
Style Number/Barcode: 06001-2082
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Satin Cowl Neck Mini Dress
Sleek, smooth, and totally elegant...we can't get enough of the satin trend either!
Fits & Features
- Cowl Neckline
- Spaghetti Straps
- Adjustable Criss Cross Ties At The Back
- Asymmetric Mini Length Silhouette
- Fully Lined
- No Zipper
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05103-0541
Category Name: Night Out
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tie Waist Velvet Skinny Pants
Perfect for the holiday season, these velvet skinny pants will make your look an instant classic! They feature a high rise waist, a tie front, and skinny pant legs with a tapered hem. The smooth velvet fabric offers moderate stretch and a form hugging fit.Style Number/Barcode: 06502-0219
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take The Plunge Satin Jumpsuit
Take the plunge and spoil yourself, because you deserve it! This satin catsuit screams night out.
Fit & Features
- Adjustable spaghetti straps
- Wired notched V neckline
- High waist seam
- Slim fitting pant legs
- Satin-like fabric
- Moderate stretch
Style Number/Barcode: 06502-0218
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sequin Star Mini Skirt
Stand out and be the star of your glam girl squad in this sequin mini skirt! Complete your look with the matching crop top.
Shop Matching Top: Sequin Star Cami Crop Top
Fit & Features
- High rise elsatic banded waist
- Short, cruve hugging fit
- Small front slit
- Knit fabric | Moderate stretch
- All over sequin embellishment
Model is 5'8" with a 32" bust, 24 waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06501-0152
Category Name: Night Out
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- High rise elsatic banded waist
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Sequin Star Cami Crop Top
Stand out and be the star of your glam girl squad in this sequin cami top! Complete your look with the matching mini skirt.
Shop Matching Skirt: Sequin Star Mini Skirt
Fit & Features
- Bungee spaghetti straps
- Square neck and back
- Cropped
- Knit fabric | Moderate stretch
- All over sequin embellishment
Style Number/Barcode: 06001-2078
Category Name: Night Out
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Faux Leather Paper Bag Pants
Edge up your workwear look with these trendy faux leather pants! They feature a high rise belted paper bag waist, two snap buttons and a hidden zipper closure, two slanted front pockets and two back pockets, and form-fitting pant legs. The faux leather fabric offers moderate stretch and include a soft lining.Style Number/Barcode: 06502-0214
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Show One Shoulder Jumpsuit
Show a little skin and embrace all your curves in the On Show jumpsuit!
Fits & Features
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One-Shoulder Neckline
- Single, Long Fitted Sleeve
- High Waist Seam
- Wide Pant Legs
- Smooth, Stretchy Mesh Composition
- Curve-Hugging Fit I Ample Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06502-0213
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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One-Shoulder Neckline
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Strappy Stretch Satin Bodysuit
Sultry and strappy, this satin bodysuit is perfect for your next night out. It features a sleeveless bodice, spagetti straps that lead to an open back with dual adjustable hortiztonal strap details, a square neck, and a thong bottom with double snap button closures. The stretch satin-like fabric offers a form hugging fit.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-2077
Category Name: Night Out
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Show Stopper Heat Stone Dress
Bring on the spotlight with this shimmering sheer dress!
Fit & Features
- V-Neckline
- Adjustable Spaghetti Straps
- High Center Slit
- Heat Stones | Iridescent Finish
- Sheer Unlined Mesh
- Relaxed Fit
- Minimal Stretch
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-0476
Category Name: Night Out
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Cat Leopard Off Shoulder Mini Dress
Leopard prints FTW. You'll be having a moment everywhere you go in the Cool Cat off shoulder mini dress!
Fits & Features
- Smocked Off Shoulder Neckline
- Roomy Cuffed Long Sleeves
- Elastic, Smocked Skirt
- Subtly Pleated, Mini-Length Hemline
- Form-Hugging Fit WIth Plenty Of Stretch
Style Number/Barcode: 05102-0397
Category Name: Night Out
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Long Sleeve Ribbed Mini Dress
Keep it cozy with this pretty knit dress! It features a plunging V neckline, long puff sleeves and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a form hugging fit.
Burgundy: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Hunter: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0365
Category Name: Night Out
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Queen Knit Crop Top
Be the stunning glitter queen you are in this gleaming crop top! It features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a cropped, form hugging fit. The glitter knit fabric offers plenty of stretch and includes a knit lining. Complete your glitzy look with the matching mini skirt!
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-2074
Category Name: Night Out
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Burnout Flocked Velvet Bodysuit
Charm them all with this must have bodysuit! It features a partially lined V neckline, long fitted sleeves and a thong bottom with snap button closure. Bodysuit is composed of a sheer mesh fabric adorned with a flocked velvet detail throughout. Bodysuit offers a form hugging fit with a moderate stretch.
Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-2073
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Wrap Front Midi Dress
You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0396
Category Name: Night Out
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Step Above The Rest Simple Block Heels
Get one step ahead of the game in a pair of simple heels! Easily styled with dress pants, or with a pair of cut off denim. These will soon become your new go-to's real fast!
- Open almond toe
- Single band over the toe
- Intricate cut out detailing
- Ankle strap with stretch
- Zipper closure back of heel
- Faux nubuck
Style Number/Barcode: 07401-0635
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crowd Pleaser Chainmail Cowl Neck Cropped Top
Babe, you are a real crowd pleaser with that style in this chainmail crop top! It features a trendy cowl neckline and a halter top chain strap. Whether you are going out for drinks, or you are heading out to a party, style this piece with faux leather bottoms or a high waist mini skirt.
Fit & Features
- Cowl neckline
- Halter top chain strap
- Adjustable lobster clasp closure
- Chain mail design
- Composed of metal
- Cropped hemline
Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0469
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance