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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Double The Fun Rhinestone Fringe Earrings
Double up on your fringe! These dazzling earrings are designed with a rainbow shaped post and feature rows of rhinestone fringe dangling down on both sides! Earrings have a post back closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0228
Category Name: Night Out
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Run Thigh High Boots
Girl you are runnin through our mind in a pair of thigh highs! These on trend boots are designed with an almond toe, a tall heel, and a lace up detail at the back. They have a zipper closure and are composed of a faux suede material.Style Number/Barcode: 07402-0084
Category Name: Night Out
Price: $23.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Casual Slay Long Sleeve Mini Dress
Oh you know, just a casual slay. This dress has all the features that we are obsessed with! A deep v neckline, an empire waist, matching buttons down the center, and long sleeves that are balloon style which adds a bohemian flare. Dress is composed of a linen material offers no stretch, and showcases a striking snake skin pattern. Lined at the skirt.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05103-0473
Category Name: Night Out
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Belted Suspender Snake Print Corset
Show Off those curves woman! This corset, features a round design that hits below the cups, spaghetti straps that are adjustable, buckle in the front, and lead to a square back with an elastic stretch backing. Corset is composed of a faux leather with a snake print pattern. Front of the corset has a double buckle golden accent.Style Number/Barcode: 07301-0090
Category Name: Night Out
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Come Thru Snake Print Clear Heeled Booties
Come thru with that style baby boo! We are loving a clear heel, so this is one for the girls that live for a trendy pair of snake print booties!
- Ankle fit
- Almond toe
- Rectangular clear lucite heel
- Inner zipper closure
- Snake print pattern
- Faux leather
Style Number/Barcode: 07403-0214
Category Name: Night Out
Price: $24.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sparkle Queen Glitter One Shoulder Mini Dress
YASS QUEEN! Make every walkway your runway!
Fits & Features
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Slanted One Shoulder Neckline With Dual Spaghetti Straps
- Zipper With Hook & Eye Closure At Back
- Linear Seaming Details
- Mini Length Silhouette With Notched Slit
- Glitter Knit Composition I Fully Lined
- Curve Hugging Fit I Slight Stretch
- Glitter May Transfer
Style Number/Barcode: 05103-0472
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slanted One Shoulder Neckline With Dual Spaghetti Straps
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Side Slit Mini Skirt
Slide on this mini skirt for a sultry look! It features a high rise waist, double front vetical seams, and a short hem with a slit. The knit fabric offers moderate stretch and a form hugging fit.
Black: Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06501-0237
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dusted In Diamonds Necklace Set
Doll yourself up tonight! This set includes a pair of rhinestone chandelier earrings that have a post back closure, as well as a beautiful rhinestone necklace! Necklace is designed with a thick structured v shape, sparkling rhinestones, and a lobster clasp closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07002-0204
Category Name: Night Out
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What A Stunner Mini Dress
Classic and stunning, this mini dress is a perfect workwear option.
Fits & Features
- V Neckline
- Long Fitted Sleeves With Shoulder Padding
- Back Zipper With Hook & Eye Closure
- Front High Waist Seam
- Mini Length Silhouette
- Ponte Knit Composition I Fully Lined
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05103-0465
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Faux Suede Snake Print Mini Skirt
Style it up in trendy snake print in this smooth faux suede mini! The skirt features a high rise waist, a back zipper and hook and eye closure, and a short, form hugging fit. The faux suede fabric offers moderate stretch.Style Number/Barcode: 06501-0114
Category Name: Night Out
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Cut Out Mini Dress
Light up the room from the moment you walk in with plenty of glitz and glam! This mini dress brings the shine girl!
Fit & Features
- Square Neckline
- Padded Cups
- Spaghetti Straps
- Bar Strap
- Asymmetrical Hem
- Fully Lined, Lurex Fabric
- Form Hugging Fit | Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0372
Category Name: Night Out
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dazzling Glitter Glow Midi Dress
Glow from the inside out with this dazzling midi dress!
Fits & Features
- Square Neckline
- Corded Straps
- Waist Cut Out
- Midi Length Silhouette
- Lined Glitter Knit Fabric I Moderate Stretch
- Zipper Not Included
- Glitter May Transfer
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0373
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Own Knit Midi Dress
Own your look with all the confidence in this knit midi dress! It features a sleeveless bodice, spaghetti straps that lead to a square back, a V neckline, a high waist band, and a mid-length, form hugging fit with a back slit. Knit fabric offers moderate stretch.Style Number/Barcode: 05101-0368
Category Name: Night Out
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Cut Out Midi Dress
Ward off the chill with this cozy for keeps midi-length dress.
Fits & Features
- Plunging V Neckline
- Long Sleeves
- Large Cut-Out Detail At Back
- Soft Knit Fabric I Fully Lined
- Ample Stretch
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0361
Category Name: Night Out
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pullin' On My Heartstrings Rhinestone Earrings
Girl you are pullin' on our heartstrings with that romantic style! Can we take u out?
- Heart outline
- Rhinestone detailing
- Dangling fringe
- Over-sized design
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0226
Category Name: Night Out
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drape And Shimmer Cowl Neck Tank Top
Drape yourself in a luxurious shimmering top! This elegant tank is designed with a cowl neck draped neckline, spaghetti straps, and a mid length hemline. Top has a slinky fit, and is composed of a shimmering knit material that offers moderate stretch.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-1939
Category Name: Night Out
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Satin Snake Print Mini Skirt
Sleek snake print is the way to go! This satin skirt pairs perfectly with the matching tank! (06001-1938)
Fit & Features
- High rise elastic banded waist
- Short, form hugging fit
- Snake print
- Stretchy satin-like fabric
- Matching tank sold separately
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06501-0112
Category Name: Night Out
Price: $15.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Scalloped Rhinestone Clutch
Bring some bling to the party! This clutch features a rectangular shape with slanted sides, and an envelope snap closure with scalloped edges. Clutch includes an inner lining with an open pocket, as well as a chain link strap that is detachable. Detailed in rhinestones this piece is the perfect pair for your special occasion outfit!Style Number/Barcode: 07204-0405
Category Name: Night Out
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cross My Heart Ring Set
Cross my heart and hope to always accessorize! This ring set def makes it easy, with the variety of designs!
- Set of 8 Rings
- Three rhinestone rings
- Two sleek rings
- Three rings with a dangling accent
- Cross | Heart | Star dangling accents
- Closed ended, no stretch
Style Number/Barcode: 07004-0039
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Puff Sleeves Top
Girl, get on that puff sleeve trend with this adorably chic top!
Fit & Features
- Crew neckline
- Short sheer puff sleeves with smocked ruffle cuffs
- Mid-length hem
- Knit fabric | Plenty of stretch
- Form-fitting style
Style Number/Barcode: 06001-1937
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Clearly The Right Choice Wedge Booties
Clearly, these trendy sock booties are obvi the right choice babe.
- Ankle fit
- Pointed toe
- Inner zipper closure
- Clear lucite wedge heel
Style Number/Barcode: 07403-0202
Category Name: Night Out
Price: $24.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning And Chic Mini Dress
Sleek and stunning, this mini dress will make you oh so chic. It features a mock neck, shoulder padding, long fitted sleeves with short slits, a back zipper closure, a flattering high waist seam, and a curve hugging skirt with ruched detailing. The dress is composed of a knit fabric with sheen finish and a minimal stretch.
Sizes run small. Fit model recommends purchasing one size up.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0462
Category Name: Night Out
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dakota Sequin Wrap Mini Dress
Special Occasion
You got places to be and people to see, especially during this holiday season. Sparkle and shine at all your winter soirees with the beautiful Dakota!
Fits & Features
- Plunging Deep V Neckline & Back
- Zipper With Hook & Eye Closure
- Wrap, Mini Length, Flowy Skirt
- Fully Lined, Mesh Fabric With Sequins Throughout
- Relaxed Fit
- Plenty Of Stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0281
Category Name: Night Out
Price: $27.97 $74.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle Some Feathers Tube Top
Ruffle some feathers in this too cute tube top! This trendy crop will make a stylish statement. It features a strapless square neckline with a majorly cropped hem and a knit fabric with allover feather detailing. Pair this top with faux leather pants for a night out with the girls.
Fit & Features
- Strapless square neckline
- Front feather detailing
- Back zipper and hook and eye closure
- Cropped
- Knit fabric with moderate stretch and feather detailing
Style Number/Barcode: 06003-0390
Category Name: Night Out
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance