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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Chic Stride Knit Over-The-Knee Boots
Unlock fierce style in these over-the-knee boots designed to turn heads! They feature a sleek block heel and a form-hugging design, these boots are perfect for dressing up day or night.
Fit & Features
- Block heel
- Knit material
- Over-the-knee height
- Pointed toe
- Form-hugging design
- Runs true to size
Style Number/Barcode: 07402-1044
Category Name: Night Out
Price: $19.97 $50.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Marvel In Marble Mini Skirt
You'll be such a marvel in this marble mini skirt perfect for a girl's night out! It features a high-rise waist, all-over ruching, a mini-length hem, a curve-hugging fit, and a trendy marble print pattern on a lined mesh fabric. Complete the look with the matching bustier and heels.
Shop Matching Top: Such A Marvel In Marble Bustier
Fit & Features
- High-rise waist
- Side and back ruching
- Mini-length hem
- Curve-hugging silhouette
- Marble print
- Lined mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0807
Category Name: Night Out
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Vibes Textured O-Ring Chain Belt
Achieve a trendy vibe accessorizing with this textured O-ring chain belt secured with a lobster clasp closure. Pair with a mini skirt.
Fit & Features
- Metal chain-link design
- Large O-rings
- Textured O-rings
- Lobster clasp closure
- Adjustable fit
Style Number/Barcode: 07301-1236
Category Name: Night Out
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mystic Charm Leaf Hair Pins
Give your hairdo a mystical charm by accessorizing with these hair pins featuring rhinestone leaves on a dainty wire frame. Complete your look with a layered choker necklace.
Fit & Features
- Rhinestone leaves
- Dainty wire frame
Style Number/Barcode: 07006-0359
Category Name: Night Out
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Alluring Wide-Leg Pants
Entice them all with your alluring look in these bold wide-leg pants! They feature a high-rise banded waist, a hip-hugging fit, and a flowy, relaxed, wide-leg silhouette. The textured knit fabric offers plenty of stretch. Style these chic pants with the matching crop top!
Shop Matching Top: Always Alluring Halter Crop Top
Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flowy, wide-leg silhouette
- Textured knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-2244
Category Name: Night Out
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Draw Attention Platform Stiletto Heels
Draw attention to your fabulous look with these bold platform stiletto heels. They feature an open almond toe, criss-cross toe straps, an adjustable ankle strap with a circular buckle, a platform sole, and an ultra-tall stiletto heel. Style with a glitter mesh clutch for a night out.
Fit & Features
- Open almond-shaped toe
- Criss-cross toe straps
- Adjustable ankle strap, circular buckle detail
- Heel straps
- Platform sole, ultra-tall stiletto heel
- Faux microsuede material
- Faux leather subtle cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4313
Category Name: Night Out
Price: $22.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shimmer And Glimmer Mini Dress
Shimmer and glimmer the night away in this dazzling mini! The dress features a sleeveless bodice, bungee spaghetti straps, a square neck and back, and a short, curve hugging fit with a hem that hits mid-thigh. The dress is composed of a glitter knit fabric that offers moderate stretch and includes a stretchy knit lining.Model is 5'7" with 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0212
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Dreams Midi Dress
We are totally obsessed with satin right now and we are guessing you are too! This midi dress features a v-neckline, thin spaghetti straps that lead to a square back and a hemline that flows into a floor length. Dress is composed of a satin like material that offers a relaxed fit with no stretch.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0325
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Satin Wrap Shirt Dress
Wrap yourself in sleek satin to make a stunning statement! The shirt dress features a flat collar with a plunging V neckline with subtle pleated detailing, long sleeves with a single button cuff and a mini length asymmetrical silhouette. Dress is composed of a satin-like fabric that offers a relaxed fit with minimal stretch.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0484
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter & Glam Mini Dress
Embrace all the glitter and glam in this mini dress!
Fits & Features
- High Mesh Neckline & Long Sleeves
- Inset Deep V Design
- Cut-Out With Button Closure At Back
- Velvet, Rainbow Glitter Knit Body
- Mini Length Silhouette
- Form-Flattering
Style Number/Barcode: 05103-0240
Category Name: Night Out
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Curves Ahead Bandage Midi Dress
Showcase your curves girl in this sexy bandage dress! Perfect for a date night with bae!
Fit & Features
- Sweetheart Neckline
- Adjustable Spaghetti Straps
- Bandage Straps
- Ponte Fabric
- Trumpet Hem
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-0239
Category Name: Night Out
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Executive Level Glam Fur Stiletto Heels
You are a top of the line, ahead of the game, executive level top notch bish in these fancy af faux fur rhinestone heels bae!
- Pointed open toe
- Clear band over the toe
- Rhinestone ankle band
- Pin buckle closure
- Faux fur detailing
- Clear skinny stiletto heel
Style Number/Barcode: 07401-0568
Category Name: Night Out
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Heather Heat Stones Mesh Mini Dress
Special Occasion
We are LIVIN' for this dress! You'll be shining as bright as the night sky in our gorge and fab Heather!
Fits & Features
- Elastic Shoulder Straps
- Plunging V Neckline & Back
- Mini Length Silhouette
- Fully Lined, Textured Mesh Fabric
- Heat Stone Embellishments Throughout
- Curve-Hugging Fit I Ample Stretch
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: 05001-0187
Category Name: Night Out
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feline Wild Leopard Off Shoulder Top
For that fierce fit, add this leopard outfit topper to your look! Look extra edgy by pairing it with some faux leather pants or a skirt!
Fits & Features
- Smocked Off Shoulder Neckline
- Roomy Blousant Long Sleeves With Smocked Cuffs
- Elasticized, Mid Length Hem
- Lightweight Smooth Woven Fabric I Leopard Print
- Relax Fit I Minimal Stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0588
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Girl On The Go Jumpsuit
This jumpsuit is perf for a girl-on-the-go like yourself! Look stunning and sleek from desk to dinner.
Fits & Features
- Spaghetti Straps
- Plunging Surplice V Neckline & Back
- Belt Loop I Tie Waist
- Slant Hand Pockets
- Tapered Pant Legs
- Form Hugging Fit
Black: Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Tan: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06502-0325
Category Name: Night Out
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Clear Choice Stiletto Heels
These chic clear stiletto heels are clearly the right choice for you! They feature an open pointy toe with a clear PVC adjustable ankle strap and a sleek stiletto heel. Pair these with a curve-hugging bodycon dress for your next date night.
Fit & Features
- Open pointed toe
- Clear PVC toe strap
- Clear PVC adjustable ankle strap
- Open back
- Stiletto heel
Style Number/Barcode: 07401-2485
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Linked In Style Stiletto Heels
Get linked in style with heels that bring those chic details! The heels feature a chunky chain-link ankle strap, an open square toe with a chain-link over the toe, and a stiletto heel. The heels are composed of a faux leather material. Complete look with a romper and a crossbody.
Fit & Features- Chunky chain link ankle strap
- Open square toe
- Chain link over the toe
- Stiletto heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3469
Category Name: Night Out
Price: $17.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shine In Celebration Lurex Jumpsuit
Celebrations call for glam outfits. Glow up in a jumpsuit that features a wired sweetheart neckline, long sleeves, tie-waist belt, and a straight leg. The jumpsuit is composed of a lined lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete outfit with a sphere clutch and heels.
Fit & Features
- Wired sweetheart neckline
- Long sleeves
- Tie-waist belt
- Straight leg
- Lurex knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0842
Category Name: Night Out
Price: $6.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Slay Cropped Oversized Faux Leather Bomber Jacket
Slay casual cool vibes in a faux leather bomber that features a crew neckline, zipper front closure, side pockets, long sleeves, and a cropped oversized fit. Complete with a cargo skirt and lug boots for an edgy feel.
Fit & Features
- Faux leather fabrication, sewn-in woven lining
- Crew neckline
- Long sleeves
- Zipper front closure, side pockets
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1696
Category Name: Night Out
Price: $24.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Abstract Art Satin Convertible Top
Abstract art you can wear! Slay an art gallery opening in this fierce satin crop top featuring a convertible design so you can style it multiple ways and a smocked back. Complete the look in the matching bottoms.
Shop Matching Bottoms: Abstract Art Satin Wide Leg Pants
Fit & Features
- Sleeveless, strapless neckline, non-slip grip lining
- Lightly padded bust
- Convertible multi-way wear
- Smocked back
- Cropped hem
- Abstract print, satin fabric
- Runs true to size
Style Number/Barcode: 06003-1582
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Single Scoop Strappy Back Midi Dress
Serve up a single scoop of you in this sultry midi dress for cocktail hour! It features a sleek, sleeveless, scoop neck, spaghetti straps, bodycon silhouette, and a strappy open back. Complete the look in glitzy earrings.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Strappy open-back detail
- Bodycon silhouette
- Midi-length hem
- Slinky knit fabric, knit lining, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1317
Category Name: Night Out
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Only View One Shoulder Sweater Dress
You're the best view around in this one-shoulder dress! It features a sleeveless bodice, a single strap, cutouts along the waist, a bodycon silhouette, and a side slit midi hem. Complete the look in hoop earrings and heels.
Fit & Features
- Sleeveless, one-shoulder, single strap
- Cutouts along the waist
- Side slit
- Bodycon silhouette
- Midi hem
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1489
Category Name: Night Out
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Madam Of Glam Rhinestone Earrings
Showcase your glam status for the evening in these statement earrings featuring cascading, rhinestone fringe, and a post-back closure. Complete the look in a sleek satin midi dress for a dressy event.
Fit & Features
- Cascading fringe
- Rhinestones
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1336
Category Name: Night Out
Price: $2.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Edge Low-Rise Hot Shorts
Take your style to the edge in these faux leather hot shorts at concerts, festivals, and nights out!
Fit & Features
- Faux leather woven fabric
- Low-rise waist, belt loop accents
- Hidden front hook-eye and zipper closures
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06403-1106
Category Name: Night Out
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free