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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Owning Knit Crop Top
Own the day in this cute crop! It features a one shoulder neckline, a tank-like strap, and a cropped waist with a tie-waist accent. Top is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1868
Category Name: Night Out
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek And Strappy Satin Bodysuit
Sleek and strappy, this satin bodysuit will give you a sultry chic look. It features a sleeveless bodice, adjustable spaghetti straps that lead to an open back with dual horiztontal bar strap detailing, a square neck, and a thong bottom with snap button closures. The bodysuit is composed of a satin-like fabric, offering moderate stretch and a form hugging fit.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1872
Category Name: Night Out
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Satin Lace Blouse
Chic and sleek, this satin lace blouse is perfect for you. It features long sleeves with elastic banded cuffs, a V neckline, center button down detailing, a sheer lace inset under the bust, and a mid-length ruffle hem. The top is composed of a lighweight satin-like fabric with no stretch.Style Number/Barcode: 06003-0367
Category Name: Night Out
Price: $13.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Jezebel Velvet Burnout Midi Dress
Special Occasion
Get a little frisky in our Jezebel!
Fits & Features
- Deep V Neckline
- Long Sleeve
- Long Hemline That Meets Mid-Length
- High Slit At Side
- Inner Bodysuit
- Mesh Composition With Velvet Burnout Detail
- Form-Fitting Silhouette I Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0276
Category Name: Night Out
Price: $29.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lover Of Velvet Crop Top
This holiday season, we're all lovers of velvet! This crop top is perfect for all your parties! Pair it with the matching mini skirt for a chic look.
Shop Matching Skirt: Lover Of Velvet Mini Skirt
Fit & Features
- Short puffed sleeves
- Sweetheart neckline
- Ruched detailing
- Cropped
- Smooth velvet fabric
- Moderate stretch
- Matching mini skirt sold separately
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06001-1863
Category Name: Night Out
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Make My Heart Flutter Velvet Jumpsuit
Your style makes our heart flutter! Designed with a deep V neckline, ruffled sleeves and a form fitting bodice, this jumpsuit shows those curves in all the right ways! Bodice leads down to a tapered form fitting skinny leg. Jumpsuit is composed of a velvet material that offers moderate stretch and is fully lined.
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06502-0173
Category Name: Night Out
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Clear Double Banded Stiletto Mules
It's clear to us that you look bomb in mules babe! These stiletto mules are designed with a point toe, double clear bands, an open back, and a faux leather lining. Dress the, up or pair with your fav destructed denim!
Please be advised that this style runs 1/2 size small.
Style Number/Barcode: 07401-0452
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feeling Wild Crop Top
Feel wild and free in this fierce-inspired print! It features a scoop neckline, corded straps and a cropped hem. The all over animal print is contrasted with a solid background. Top is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Be sure to pick up the matching skirt to complete your look!
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06001-1862
Category Name: Night Out
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitter Babe Mini Dress
This glitter knit mini dress is so perf for you babe! It features a sleeveless bodice, spaghetti straps that lead to triple bar back detailing, a V neckline, a high waist seam, and a short, curve hugging fit. The glitter knit fabric offers plenty of stretch. Glitter may transfer.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05103-0316
Category Name: Night Out
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Faux Leather Cabby Hat
Get ya cabby hat here, girl! This cabby hat features allover faux leather fabric with a button top and short brim.Style Number/Barcode: 07302-0015
Category Name: Night Out
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All That Shine Metallic Mini Dress
You were born to shine girl! This mini dress features a high round neckline, fitted long sleeves and dramatically draped cowl back. The slim fit fit bodice leads to a body-hugging mini length silhouette. Dress is composed of a lined metallic knit fabric that offers a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05103-0327
Category Name: Night Out
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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More Rhinestone Please Clutch
More rhinestones please! This structured clutch is all about that shine! Featuring a straight flap closure, and a hidden cross-body chain link strap. Clutch is composed of a mesh material and is fully adorned in rhinestones.
Style Number/Barcode: 07204-0030
Category Name: Night Out
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off Shoulder Long Sleeve Glittering Mini Dress
Slip into something that glitters!
Fits & Features
- Straight Off-Shoulder Neckline
- Long Fitted Sleeves
- Mini Length Silhouette
- Knit Material I Adorn In Glitter
- Form Hugging Fit I Moderate Amount Of Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05103-0264
Category Name: Night Out
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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After Hours Zip Front Mini Skirt
Kick up your night wardrobe with something that has edge! This mini is composed of a shiny patent material that offers no stretch. Skirt features two large rectangular pockets at both sides, a double button snap closure at waist line, and a full zipper closure down the center.Style Number/Barcode: 06401-0050
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Into You Faux Suede Mini Dress
You'll be so into this sleek faux suede mini dress! It features a sleeveless bodice, bungee spaghetti straps that lead to an open lattice back, a square neckline, and a short, curve hugging fit. The faux suede fabric offers plenty of stretch and includes a front knit lining.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0274
Category Name: Night Out
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Romantically Involved Mini Dress
Get yourself involved with a romantic look!
Fits & Features
- Sheer, High Crew Neckline I Sweetheart Underlay
- Unlined, Fitted Long Sleeves
- Open Back With Button Closure At Neck
- Sheer Mesh Composition With Reflective Velvet Burnout Floral Pattern
- Lined, Mini Length Skirt
- Body-Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0199
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Never Too Much Chiffon Skater Dress
There is no such thing as too much! Dress features a plunging V neckline, and spaghetti straps that cross in the back. Bodice is fitted and designed with a flirty lace overlay, and meets high waist with a double tiered hem. Dress composed of a chiffon material that is light weight and offers slight stretch. Zipper located lower back.
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0150
Category Name: Night Out
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keepin' Knit Casual Midi Dress
This knit midi is casual yet oh so cute. It features a sleeveless bodice, adjustable spaghetti straps, a sweetheart neckline with bust stitching, and a mid-length, curve hugging fit with a back slit. The ribbed knit fabric offers plenty of stretch.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0202
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry Satin Square Neck Tank
Sultry and so chic, this tank is the perfect addition to your wardrobe. It features a sleeveless bodice, tank-like shoulder straps, a trendy square neck and back, and a mid-length, form hugging fit. The satin-like fabric offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-1775
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Natural Attraction Mini Knot Dress
Create a natural attraction with a simply flattering look! This mini dress features a v neckline, long sleeves that puff at the wrist with a thick band, and a front knot detailing at the center of the bodice. Skirt meets bodice with a wrap design and an asymmetrical hemline that meets mid thigh. Dress is composed of a smooth knit material with a sheen reflection and moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0200
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Satin Sweetheart Ruffle Mini Dress
Sleek and stunning, this satin mini is your new fave for sure.
Fits & Features
- Ruffle Detail Shoulder Straps
- Square Back With Hidden Zip & Hook Eye Closure
- Sweetheart Neckline With Wired Bust
- Mini Length Silhouette
- Satin-Like Fabric I Knit Lining
- Plenty Of Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0259
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Cutie Cargo Joggers
Your everyday lineup just got way more interesting. These high-rise cargo joggers bring utility attitude with utility pockets, a straight-leg fit, and a removable graphic strap for an extra hit of personality.
Fit & Features
- Twill cotton-blend woven fabric
- High-rise waist
- Single-button and zipper closure
- Slanted pockets and cargo-style pockets
- Removable graphic strap reading "Good Vibes"
- Straight-leg fit with elastic cuffed jogger hems
- Runs true to size
Style Number/Barcode: 06302-0162
Category Name: Night Out
Price: $46.90
Availability: In Stock
Available Color: OLIVE, BLACK
Available Size: XS, S, M, L
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Shine On Glitter Mini Dress
Shine on bby! This glowing mini features a sleeveless bodice, a V neckline, spaghetti straps and vertical princess seams. The back features a scoop back design accented with a triple-row bar strap detail. The slim fit bodice leads to a flared skater length silhouette. Dress is composed of a lined glitter knit fabric that offers a form hugging fit with a moderate stretch. Glitter may transfer.
Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05103-0317
Category Name: Night Out
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sneaky As A Snake Sequin Midi Dress
Sneak into some snake print this season! This midi features a square neckline, spaghetti straps that lead to a square back, and a form fitting silhouette. Dress is designed with sequins and composed of a knit material that offers slight stretch and sow a subtle snake print pattern.
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small
Style Number/Barcode: 05103-0328
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance