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.
Now Trending
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.
-
Sugar Sugar Ankle Fit Booties
Hey there suga! If you're obsessed with nude tones, and booties, then we are here for you! This pair is composed of a faux leather and features an almond toe, a high heel, a side zipper closure, and fitted ankle fit.Style Number/Barcode: 07403-0115
Category Name: Night Out
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Gold Trim Faux Suede Booties
These boots have that little something extra that you're looking for! Designed with an almond toe, an ankle fit, and a low heel with a gold trim. They are composed of a faux suede and include a zipper closure.Style Number/Barcode: 07403-0116
Category Name: Night Out
Price: $11.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fantasy Chain Belt
You're a fantasy in this belt, babe! This chain belt features layered ring accents that add a feminine touch to any outfit. Featuring a lobster clasp closure and extender for the perfect fit.Style Number/Barcode: 07301-0077
Category Name: Night Out
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Rosalynne Sequin Gown
Special Occasion
Step out in our Rosalynne. She is a beautiful, floor-length, fully lined sequined gown, with a square neckline, a tank bodice with v back, and hidden zipper closure. She features a sexy high thigh slit at the leg and a flattering form fit. She is composed of a sequin knit fabric that offers minimal stretch.
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0080
Category Name: Night Out
Price: $24.97 $66.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Keep It Lurex Box Clutch
Let your accessories steal the spotlight when you carry this convertible Lurex clutch. The purse has a structured, box-style construction and features metallic threading and contrast satin lining, a magnetic snap closure, and a detachable silver-tone shoulder strap. Complete the look in a club dress for a girl's night out!
Fit & Features
- Structured box-style construction
- Magnetic snap closure
- Metallic threading
- Detachable silver-tone shoulder strap
- Contrast satin lining
- Spacious interior
Style Number/Barcode: 07204-0034
Category Name: Night Out
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
All The Trimmings Crochet Dress
This lovely lace crochet mini is all about the eye-catching detail! Skater-style dress features a solid underlay and large-weave crochet overlay, spaghetti straps, a fitted bodice with V neckline and back zip, and a swing-y A-line skirt. Dress is fully lined and made from lightweight woven materials with minimal stretch.Style Number/Barcode: 05101-0030
Category Name: Night Out
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Liza Satin Mesh Party Dress
Special Occasion
Ready for an epic evening? Then light up the night in our lovely Liza dress! She features a strapless, seamed sweetheart bodice with light padding at bust and a back zip. Liza's A-line satin skirt has pockets and sits atop a structured mesh-tulle underlay, giving her party-perfect volume. Liza is lined and made from a smooth, shiny cotton blend with moderate stretch.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0022
Category Name: Night Out
Price: $29.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
High Waist Faux Leather Skinny Pants
Add some serious edge to your look with these faux leather skinny pants! They feature a high rise waist, the traditional five belt loop design, faux front pockets, two back pockets, a hidden zipper and front button closure, and a slim fit throughout the leg. The faux leather fabric offers moderate stretch and a form hugging fit.
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06402-0060
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Hourglass Sleeveless Sweater Dress
An LBD that perfectly contours your curves? Yep! This sultry-yet-streamlined midi features all-over sweater-style ribbing, a tube bodice with elasticized bust, and a pencil skirt. Dress slips on, has a body con cut, and is made from a rayon and nylon blend with natural stretch.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06005-0174
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Susan Formal Sleeveless Midi Dress
Special Occasion
Keep it sleek and sophisticated in our timelessly elegant Susan dress! She features a strapless sweetheart neckline, a built in no slip strip, padded cups, pleating accents along the bust, an empire waist accent and trendy side pockets. She is composed of a lined crepe fabric that offers a form hugging fit and a moderate stretch. Includes a back zipper closure with a hook and eye closure.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0027
Category Name: Night Out
Price: $29.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Oh La La Wool Beret
Oh la la, this wool beret is oh so chic! It features a rounded classic floppy look, and is perfect for the fall season!Style Number/Barcode: 07302-0030
Category Name: Night Out
Price: $6.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Rhinestone Bollo Tie Bracelet
Keep it dazzling and simple with this eye catching bollo bracelet! It features a single row of micro double sided cubes embellished with twinkling rhinestone and an adjustable bollo closure that adjusts for a custom fit.
Style Number/Barcode: 07003-2180
Category Name: Night Out
Price: $8.90
Availability: Out of Stock
Product Badge:- Clearance
-
Two To Tassel Earrings
Take a step into your chic side with these tassel earrings! They feature a cluster of large faceted gems, and three hanging tassels. Earrings have a post back closure.
Style Number/Barcode: 07001-4307
Category Name: Night Out
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
More Glow Lace Bustier
Need more glow? Add this bustier top to your 'fit! It features a sleeveless bodice, a flattering underwire, sweetheart bust, adjustable spaghetti straps, a back hook and eye closure, and a pretty eyelash trim detail. The top is composed of a sheer lace fabric with a form-fitting style.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-0093
Category Name: Night Out
Price: $8.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Must Have Block Heels
These basic cute block heels are a definite must have! They feature an open toe with a single strap design, an adjustable ankle strap, a closed back, and a sturdy block heel. The heels are composed of a smooth nubuck material.
Style Number/Barcode: 07401-0072
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Draped 3 Row Chain Belt
Level up your festival wear with this chain belt! It features three rows of chains that drape across your hip, and an adjustable single back chain with a lobster clasp closure.
Style Number/Barcode: 07301-1050
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Strut In Style Block Heels
Own your look and strut in style with these fab block heels! They feature an open toe with a single strap, an ankle strap, a back zipper closure, and a block heel. The black shoes are composed of a smooth faux nubuck material.
Style Number/Barcode: 07401-2093
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Snake And Slide Mule Heels
An easy but always sexy go to look! These must have mule heels feature a snake print, a two strap upper, and a wide stiletto heel.
Sizes run small. Fit model recommends purchasing one size up.
Style Number/Barcode: 07401-2086
Category Name: Night Out
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Buckle Up Block Heels
Buckle up in these statement making heels! They feature a mustard hue, a closed back, an wide adjustable ankle strap with buckle, an open toe with single strap and a block heel. They are composed of a faux suede material and faux leather insole lining.
Style Number/Barcode: 07401-2073
Category Name: Night Out
Price: $21.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Easy Day Cross Strap Sandal Heels
Slip these on for an easy but always chic look! These tan sandal heels feature a crossed strap upper with an open toe, a thin ankle strap with buckle, and a short stacked heel.
Style Number/Barcode: 07401-2083
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
The One Platform Heel
This is the one essential heel you need to complete your looks! It features a trendy hue, a closed back, an adjustable ankle strap, an open toe with single strap, a wide platform and a block heel. They are composed of a faux nubuck material.
Style Number/Barcode: 07401-2035
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Criss Cross And Tell Block Heels
Spill the juicy details in these hot heels! They feature an open almond toe design, a criss cross strap upper, a back zipper closure, and a block heel. Complete the look in a chic mini dress for a night out.
Fit & Features
- Open almond toe
- Block heel
- Crisscross upper
- Back zipper closure
- Runs true to size
Style Number/Barcode: 07401-2571
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Timeless Rhinestone Strap Heels
These timeless heels will pair perfectly with any dress! They have an adjustable ankle strap, an open toe design with a single strap adorned with rhinestones, a high block heel, and a smooth nubuck material.
Style Number/Barcode: 07401-1977
Category Name: Night Out
Price: $18.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Comfort Wide Fit Chic Block Heels
Make your 'fit effortlessly chic with these sleek block heels! They feature an open toe with a single strap, a thick ankle strap with a velcro closure and a block heel. The black heels are composed of a faux nubuck material.Heels offer a comfortable wide fit
Style Number/Barcode: 07401-3795
Category Name: Night Out
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale