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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Own The Night Sequin Mini Skirt
Own the night in a fierce attire! Designed fully in sequins this mini skirt is one for the books! Featuring an elastic high waist line, a zipper closure at the back and a full lining. Hem hits mid thigh, and skirt is composed of a knit material that offers a form fitting silhouette and slight stretch.Style Number/Barcode: 06501-0164
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Show 'Em Off Shoulder Smocked Mini Dress
Show off those shoulders in this cute mini dress! For a cute daytime look, pair it with your fave denim jacket and some white sneakers!
Fits & Features
- Off-shoulder neckline, short sleeves
- Keyhole opening with self-ties at front
- Mini length silhouette
- Woven textured fabric, smocked back, ruffle trim detail
- Curve hugging fit, plenty of stretch
Style Number/Barcode: 05102-0472
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Diva Glitter Knit Mini Dress
This glitter knit dress was made for a fashion diva! It features a sleeveless bodice, spaghetti straps, a cowl neck and a square back, a high waist seam, ruched side detailing with drawstrings at the hem, and a short, curve hugging fit. The knit fabric offers moderate stretch.Style Number/Barcode: 05103-0556
Category Name: Night Out
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V Right There Asymmetrical Mini Dress
The party doesn't start until you walk in! Slay the night away in the V Right There mini dress!
Fits & Features
- Wrap V Neckline
- Spaghetti Straps Lead To Cut-Out Design And Adjustable Ties At Back
- Slight Ruching At The Top Side Seams
- Asymmetrical Hemline
- Stretch Knit Fabric I Moderate Stretch
Style Number/Barcode: 05101-0449
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Strapless Cargo Pocket Jogger Jumpsuit
Step out in a sleeveless cargo jumpsuit for a night out. This must-have jumpsuit features an elastic straight strapless neckline, a drawstring tie waist, and slant pockets. The straight jogger leg features cargo-styled pockets and an elastic cuff. The jumpsuit is composed of lightweight woven fabric that offers a form hugging fit. Complete your night out look with a chic crossbody and sleek heels.
Fit & Features
- Sleeveless straight elastic neckline
- Drawstring waist
- Slant pockets
- Straight jogger leg with elastic cuff
- Lightweight woven fabric
- 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: 06302-0087
Category Name: Night Out
Price: $14.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tamra Cross Neck Midi Formal Dress
Special Occasion
Try out a little soft glam in our Tamra formal midi dress! She is sexy, sultry and gives you that soft touch of glam!
Fit & Features
- Cross neckline
- Sleeveless
- Form fitting silhouette
- Mid-length hem that hits mid-calf
- Small slit center front
- Zipper located center back
- Moderate stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0325
Category Name: Night Out
Price: $29.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Waist Trendy Cut Out Skinny Jeans
These trendy high waist cut out skinny jeans will amp up any casual look and make it even edgier! They feature a high rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, dramatic front cut outs, and slits below the back pockets. The jeans are composed of a stretchy denim fabric and offer a form-hugging fit. Complete your outfit with a chic crop top and clear heels.
Fit & Features
- High rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Front cut outs
- Slits below the back pockets
- Stretchy denim fabric
- Form-fitting style
- Runs true to size
Style Number/Barcode: 06602-0062
Category Name: Night Out
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stretch Satin Mini Skirt
We all need a go-to satin skirt. It's such an essential to have in your wardrobe!
Fit & Features
- High rise elastic banded waist
- Short, ruffle hem with drawstring detail to cinch
- Stretchy satin-like fabric
Style Number/Barcode: 06501-0161
Category Name: Night Out
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Velvet Snake Print Midi Skirt
Snake print and velvet?! Girl, yes please! This midi skirt will keep you on trend.
Fit & Features
- High rise elastic banded waist
- Mid-length, form hugging fit
- Center back slit
- Snake print
- Smooth velvet fabric | Plenty of stretch
Style Number/Barcode: 06501-0162
Category Name: Night Out
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lyla Formal Crepe Midi Dress
Special Occasion
Keep it sophisticated and stunning in our Lyla dress! She takes it to the next level with her must have pockets!
Fit & Features
- Sweetheart Neckline
- No-Slip Strip
- Padded Cups
- Empire Waist
- Pockets
- Lined Crepe
- Form Hugging Fit | Moderate 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: 05001-0324
Category Name: Night Out
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take A Second Look Romper
Everyone will be taking a second look as you pass by in this chic romper!
Fit & Features
- Collared
- Long sheer organza sleeves with cuffs
- High waist seam
- Faux wrap front detail
- Fitted shorts
- Crepe fabric | Moderate stretch
Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06503-0085
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Metallic Muse Ruched Midi Dress
Be an alluring muse in this metallic ruched midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, flattering princess seams, and a square back with a zipper and hook and eye closure. The sultry front waist cut out leads to a mid-length curve hugging skirt with ruched detailing. The metallic knit fabric has ample amount of stretch and includes a knit lining.Style Number/Barcode: 05103-0555
Category Name: Night Out
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lace Is More Crop Top
It's all about the lace with this trendy crop top!
Fit & Features
- Short puffed sleeves | Elastic banded cuffs
- Square neckline
- Ruched front detailing
- Lace up back | Satin ribbons
- Cropped
- Sheer floral lace fabric | Knit lining
- Moderate stretch
Style Number/Barcode: 06001-2106
Category Name: Night Out
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Low Ruffle Hem Satin Dress
Look party-ready with this elegant and sultry high-low dress!
Fits & Features
- Spaghetti Straps That Cross At Back
- Square Neckline I Vertical Darts At The Bust
- High-Low Hem With Ruffle Trim Detail
- Satin-Like Composition I Fully Lined
- Body-Hugging Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0438
Category Name: Night Out
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ringing In The New Year Ring Set
Ring in the new year with your fingers frosted and sparklin' like no other when you cover them in a set of dainty rhinestone rings!
- Set of five
- Dainty circular rhinestones
- Open ended
- Slight stretch
- Memory wire
Style Number/Barcode: 07004-0051
Category Name: Night Out
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fine In Rhine Mini Dress
Okay, we see you! Make an entrance in the Fine In Rhine mini dress!
Fits & Features
- Scoop Neckline I Square Back
- Fixed Spaghetti Straps
- Mini Length Silhouette
- Curve-Hugging Fit
- Fully Lined, Textured Knit With Rhinestone Embellishments Throughout
- Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0554
Category Name: Night Out
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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That's A Look Velvet Bodysuit
Get a sultry stylish look in this of the moment bodysuit. It features a high neck, long fitted sleeves, a large front keyhole cut out, and an exposed back zipper closure. Bodysuit is composed of a smooth velvet fabric, offering a form hugging fit with moderate stretch.
Style Number/Barcode: 06001-2102
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Loving Knit Wrap Front Bodysuit
You'll fall head over heels in love with this soft knit bodysuit! It features a surplice front creating a V neckline, long fitted sleeves, a flattering high waist seam, and a thong bottom with dual snap button closures. The brushed knit fabric offers moderate stretch and a form-fitting style.Style Number/Barcode: 06001-2104
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Nova Ruched Sides Midi Dress
Special Occasion
Dress to impress with our Nova! Classically elegant, she features ruching for a curve-flattering fit.
Fits & Features
- High Neckline
- Fitted Long Sleeves
- Ties At The Open Back
- Midi Length Silhouette With Ruching
- Smooth Tricot Knit Fabric I Fully Lined
- Body-Hugging Fit I Moderate Stretch
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0321
Category Name: Night Out
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Forever Fringe Crop Top
You'll forever be in love with the boho chic vibe of this fringe crop top! Pair with some high waist faux leather shorts and over the knee western boots for that instant festival 'fit.
Fit & Features
- Adjustable spaghetti straps
- Deep V neckline
- Front cascading fringe detailing
- Cropped
- Knit fabric | Plenty of stretch
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-2096
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Adjustable spaghetti straps
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Hit The Lights Tie Waist Crop Top
Hit the lights, because you're going to be the spotlight of the room in this crop top!
Fit & Features
- One shoulder neckline
- Cropped
- Tie waist detail
- Glitter lurex knit fabric
- Moderate stretch
Style Number/Barcode: 06001-2095
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Heat Stone Mesh Puff Sleeve Top
Heat up the party scene in this embellished mesh trendy top!
Fit & Features
- Mock neckline
- Long fitted sleeves with puff shoulders
- Double back button closures | Keyhole cut out
- Mid-length form-fitting hem
- Heat stone embellishments
- Sheer mesh fabric | Moderate stretch
Style Number/Barcode: 06001-2093
Category Name: Night Out
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tied To Ruched Mini Dress
Get tied to this pretty ruched trend to showcase curves in all the right places!
Fit & Features
- Crew Neckline
- Long Sleeves
- Ruched Drawstring
- Form Hugging Fit
- Moderate Stretch
- Fully Lined
- No Zipper
Style Number/Barcode: 05103-0548
Category Name: Night Out
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glamorous Girl Mini Skirt
Shop Matching Top: Glamorous Girl Crop Top
You're a total glam girl at heart, so this sequin adorned mini skirt is a perfect match. It features a high rise waist, a back zipper and hook and eye closure, and a short, form hugging fit. The mesh fabric includes a front and back knit lining and offers moderate stretch. Complete your glitzy look with the matching crop top!
Style Number/Barcode: 06401-0123
Category Name: Night Out
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance