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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Ruched Hour Mini Dress
This fiery number is calling your name. You'll be stopping traffic in this one!
Fits & Features
- Dual Shoulder Straps
- Square Neckline
- Ruched Drawstring
- Form Hugging Fit
- Moderate Stretch
- Fully Lined
Style Number/Barcode: 05102-0433
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Misty Off Shoulder Glitter Dress
Special Occasion
You'll be channeling princess vibes in this one. Look magical in our glistening Misty dress!
Fits & Features
- Off Shoulder Neckline I Fold Over Design
- Back Zip With Hook & Eye Closure
- Midi Length Silhouette I Front Slit
- Glitter Lurex Fabric I Fully Lined
- Curve Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0330
Category Name: Night Out
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sofia Formal Sequin Midi Dress
Special Occasion
Shine for those moments that count the most in our shimmering Sofia dress! She features a high neck with a racer bust and a flattering midi length silhouette with mini side slit. She features dazzling sequins set in a scroll print design for an elegant touch! Dress is composed of a lined mesh fabric that offers a relaxed fit with minimal stretch. Includes a back zipper closure with fish hook clasp fasten.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0332
Category Name: Night Out
Price: $30.97 $89.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Purely Pearl Chain Belt
We love to add a feminine touch with pearls! This belt is designed with two rows of pearls that are woven together with a beautiful chain. Belt has an adjustable lobster clasp closure.Style Number/Barcode: 07301-0111
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce Competition Satin Blouse
Everyone will have some fierce competition with you in this tiger print satin blouse! It features a collar, long sleeves with double buttons to cuff, a complete button down front, top buttoned pockets, and a flowy, relaxed fitting style. The satin-like fabric has no stretch.Style Number/Barcode: 06003-0528
Category Name: Night Out
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Peep Toe Thigh High Boots
Peep that pedi girrrl! This pair of thigh high boots are designed with a slip on form fit, an almond toe, a peep toe, a cut out at the heel of the foot, and a stacked wooden high heel. They are composed of a nylon material that offers a little bit of stretch.Style Number/Barcode: 07402-0114
Category Name: Night Out
Price: $29.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Little Sparkle Platform Heels
Finish your look with a touch of sparkle! These high heels are designed with an almond toe, a rhinestone band across and, a closed heel with a thin ankle strap that has an adjustable pin buckle closure. Heels are composed of a faux nubuck material and offer a short platform, and a high heel.Style Number/Barcode: 07401-0728
Category Name: Night Out
Price: $22.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Shine Through Glitter Mini Dress
This hard-to-miss mini dress will make an entrance! Featuring a flattering scoop neckline, spaghetti straps, a front slit, and a form-hugging fit to enhance your curves, this mini-length dress is perfect for your next GNO. The glitzy glitter knit fabric has a moderate stretch. Pair with some strappy heels for a gorgeous look.
Fit & Features
- Sleeveless scoop neckline, spaghetti straps
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Textured knit fabric, knit lining at the bust, moderate stretch
- Glitter may transfer
- Runs true to size
Style Number/Barcode: 05103-3778
Category Name: Night Out
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Sleeveless scoop neckline, spaghetti straps
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Acting Right Square Toe Faux Leather Heels
Get yo act together in a pair of sleek faux leather heels babayy! Style with dress pants or a midi skirt and make power moves!
- Open square heel
- Single band over the toe
- Thin rectangle heel
- Ankle strap
- Adjustable pin buckle closure
- Faux leather
Style Number/Barcode: 07401-0703
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crushin' On U Rhinestone Platform Heels
Girl we are crushin' on you in those eye catching sparkling heels! Style with flared pants, or a jumpsuit for vintage disco vibez-
- Open almond toe
- Platform sole
- Tall block heel
- Single band over the toe
- Rhinestone detailing
- Ankle strap with adjustable pin buckle closure
- Faux nubuck
Style Number/Barcode: 07401-0702
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Let Them Look Thigh High Boots
Let them look, let them stare, because they are lovin' your style with those thigh high boots babe!
- Thigh high fit
- Almond toe
- Low block heel
- Lace back detailing
- Inner zipper
- Faux suede
Style Number/Barcode: 07402-0118
Category Name: Night Out
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Play It Up Lace Up Thigh High Boots
Play up your look a little with a pair of thigh highs gurrl! We are lovin' a little lace up detail to add a lil somethin' to your look!
- Thigh high fit
- Lace up detailing
- Almond toe
- Block heel
- Inner zipper closure
- Faux suede
Please be advised that this style runs 1/2 size small.
Style Number/Barcode: 07402-0117
Category Name: Night Out
Price: $27.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Carine Metallic Glitter Ruched Mini Dress
Special Occasion
Almost instantly, Carine's glitter metallic shine will draw eyes your way. You'll be loving her figure-flattering fit that'll have you look and feel amazing. Don't forget to include some stiletto heels and earrings to really finish the look!
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Padded Bust
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Ruched Down Center Front, Back & Sides
- Smooth Woven Glitter Knit I Fully Lined
- Form Hugging Fit I Minimal Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0326
Category Name: Night Out
Price: $36.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sequin Dreams Wrap Mini Dress
Strutting this stunning sequined fit will get you double-takes everywhere you go!
Fits & Features
- Wrap V Neckline With Button Closure
- Long, Unlined Sleeves
- Removable Sequin Waist Belt
- Mini Length Silhouette
- Lined, Sequined Mesh Composition
- Form Hugging Fit I Moderate Stretch
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Pink: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0455
Category Name: Night Out
Price: $21.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Chiffon Lace-Up Milkmaid Blouse
We love you in a lil' leopard print babe! Keep it light and fresh in a chiffon blouse that practically makes your outfit! Pair with high waist pants and booties for an effortlessly trendy vibe!
Fit & Features
- Square neckline
- Milkmaid design
- Lace-up detailing down the center
- Button detailing at cuffs
- Mid-length hemline
- Sheer chiffon | Lined at the cups
- No stretch
Style Number/Barcode: 06003-0518
Category Name: Night Out
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Edge It Up Faux Leather Mini Dress
Edge up your look with this sleek faux leather mini! The dress features a sleeveless bodice, adjustable spaghetti straps, a sweetheart neckline with molded and padded cups and a sexy notch detail, a high waist seam, and a short, form-fitting hem with a front slit. The fabric offers moderate stretch.Style Number/Barcode: 05103-0558
Category Name: Night Out
Price: $16.97 $42.90
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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High Key Diva Rhinestone Stiletto Heels
For the high key diva, a pair that shines like no otha! Style with a glitter mini dress, or a gown fit for a special occasion!
- Open almond toe
- Single rhinestone strap over the toe
- Short platform
- Adjustable ankle strap with pin buckle closure
- Stiletto heel
- Full rhinestone over chrome
- Faux leather padded lining
Style Number/Barcode: 07401-0694
Category Name: Night Out
Price: $12.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Sleeveless Ruched Satin Bodysuit
Keep it fab in this must have bodysuit! It features a sleeveless bodice, a scoop neckline with ruched accent, adjustable spaghetti straps and a thong bottom with snap button closure. Bodysuit is composed of a lined satin fabric that offers a form hugging fit with a moderate stretch.
Style Number/Barcode: 06001-2127
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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There You Go Rhinestone Block Heels
Pair these stunning rhinestone block heels with your most glamourous outfits! Dazzle at your homecoming in heels that bring the luxe. The heels feature a rhinestone embellished block heel and a matching embellished ankle strap. Complete your formal outfit with a sweeping mermaid dress and clutch.
Fit & Features
- Open almond toe
- Crisscross straps
- Rhinestone ankle strap
- Adjustable pin-buckle closure
- Rhinestone embellished block heel
- Faux suede
Style Number/Barcode: 07401-0696
Category Name: Night Out
Price: $21.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Loving In Lace Bodysuit
Keep it lovely in lace! The bodysuit features a mock neck, long sleeves and a small keyhole at the nape of neck. Bodysuit is composed of a sheer unlined lace fabric that offers a relaxed fit with slight stretch. Includes a thong bottom with snap button closure.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-2129
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sequined Charmer Mini Dress
Be prepared for double-takes in the Sequined Charmer mini dress!
Fits & Features
- Crew Neckline
- Long Sleeves With Ribbed Cuffs
- Dual Button Closure At Back Neck
- Adjustable Lattice Detail & Zipper Closure At Back
- Mini Length Silhouette
- Sequined Mesh Composition I Fully Lined At Body & Skirt
- Curve Hugging Fit I Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0450
Category Name: Night Out
Price: $26.97 $66.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance