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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Wild Sparkle Leopard Print Sequin Mini Skirt
The mini skirt features a high-rise waist, a trendy leopard print, clear sequins, and a high-side slit. Complete the look with the matching crop top for the ultimate GNO outfit!
Shop Matching Top: Wild Sparkle Leopard Print Sequin Crop Top
Fit & Features
- Woven knit fabric with knit lining, moderate stretch
- Leopard print, all-over clear sequin embroidery
- High-rise waist
- Side zipper with hook-eye closure
- High-side slit
- Mini-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06401-0708
Category Name: Night Out
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Swirls V-Neck Mini Dress
Perfectly swirled and smoothed to perfection! Showcase a head-turning look in this sleeveless mini dress featuring a v-neck, bungee spaghetti straps, bodycon silhouette, slit accent, and a marble print on brushed knit fabric. Complete the look in lace-up heels for a summer party.
Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Marble print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4660
Category Name: Night Out
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rhythm And Shine Sequin Mesh Dress
Move to the rhythm and shine under the lights in this sequin mini dress to captivate the club! It features a sleeveless sweetheart neck, spaghetti straps, a built-in padded bust, a mesh insert bodice with satin trim, and a bodycon silhouette. Complete the look with a metallic clutch.
Fit & Features
- Sleeveless sweetheart neck, spaghetti straps
- Built-in padded bust
- Back zipper and hook-eye closure
- Mesh insert bodice, satin trim
- Bodycon, mini-length hem
- Sequin fabric, knit lining, minimal stretch
- Fits true to size
Style Number/Barcode: 05103-4729
Category Name: Night Out
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Order Satin Wrap Tie Top
You'll be the chicest thing on the menu! Serve up major looks in this satin crop top featuring long bell sleeves, a plunge-open neckline, and a wrap-tie string that lets you customize the style. Complete your outfit in a mini skirt for dinner and drinks!
Fit & Features
- Long bell sleeves
- Plunge-open neckline
- Wrap-tie design
- Cropped hem
- Smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1892
Category Name: Night Out
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shimmer Down Rhinestone Block Heels
Shimmer down to your toes in these rhinestone block heels featuring an open square toe, wide toe strap, and closed ankle with an adjustable buckle strap. Complete the look with an embellished clutch.
Fit & Features
- Open square toe
- Wide toe strap
- Block heel
- Closed ankle with adjustable buckle strap
- Rhinestone embellsihed
- Runs true to size
Style Number/Barcode: 07401-3968
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Memorable Shine Metallic Round Block Heels
Step out in these metallic round-block heels sure to make a lasting impression! They feature a sleek square toe, thin toe strap, a crisscross ankle strap with buckle closure, and are composed of faux leather material. Complete the look in a sassy LBD for dinner and drinks!
Fit & Features
- Square toe
- Thin toe strap
- Crisscross ankle strap, buckle closure
- Round block heel
- Metallic faux leather material
- Runs true to size
Style Number/Barcode: 07401-4143
Category Name: Night Out
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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It-Girl Moment Crepe Bow Mini Dress
Have your it-girl moment in this crepe mini dress at cocktail parties or dressy birthdays! It features a sleeveless square neck, adjustable spaghetti straps, a statement bow on the back, and a bodycon silhouette. Complete the look in sassy stiletto heels.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Statement bow on the back
- Bodycon silhouette
- Mini-length hem
- Crepe fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2441
Category Name: Night Out
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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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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Be About It Double Band Clear Wedges
Be about it and walk with confidence in the cutest wedges of course! Style with your fav mini dress or high waist jeans!
- Open almond toe
- Double band design
- Clear lucite wedge
- Slide on fit
Style Number/Barcode: 07406-0052
Category Name: Night Out
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dose Of Sultry Lace Bodycon Ruffle Mini Dress
Add a dose of sultry to your night in this lace mini dress for cocktail hour! Featuring detachable and adjustable spaghetti straps, a sweetheart neckline, and padded bra cups for support and comfort. The sheer bust insert adds a touch of sexy, while the ruched bodycon silhouette and ruffled mini-length hem accentuate your figure. Complete the look with earrings.
Fit & Features
- Lace fabric lined with stretchy knit
- Detachable and adjustable spaghetti straps
- Sweetheart neckline
- Padded bra cups
- Back zipper and hook-eye closure
- Ruched bodycon silhouette, ruffled hem
- Runs true to size
Style Number/Barcode: 05101-3350
Category Name: Night Out
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Layer It On Lariat Chain Necklace Set
Layer your look in a little bit of silver, or a lot a bit! This set of four necklaces are perfectly paired with a graphic tee and chunky silver hoops for an effortlessly trendy lewk!
- Set of four necklaces
- Dainty necklaces
- One link style necklace
- One lariat drop stone necklace
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0381
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daydreaming Platform Espadrille Wedges
Daydreaming of a day on the beach wearing these stunning wedges and a flowing maxi dress!
- Square toe
- Single clear band over the toe
- Wrap around ankle strap
- Platform design
- Wedge espadrille heel
- Available in : Black croc print | Metallic gold | Faux leather snake print
Please be advised that this style runs 1/2 size large.
Style Number/Barcode: 07406-0099
Category Name: Night Out
Price: $22.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Eyes On You Mesh Mini Skirt
All eyes will for sure be on you in this trendy mini skirt! It features an overall form-hugging fit with a mesh fabric with a detailed geometric print. Pair this skirt with sleek gold hoop earrings for a gorgeous look.
Shop Matching Top: All Eyes On You Crop Top
Fit & Features
- High rise waist
- Short, form-fitting style
- Mesh fabric
- Allover geometric print
Style Number/Barcode: 06501-0328
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Tie Back Crop Top
Get tied to this chic crop top that showcases your wild sense of style! The top features an animal print, sweetheart neckline, long sleeves, a cropped hem, and a lower back keyhole with tie back detail. Complete look with high waist jeans.
Fit & Features
- Sweetheart neckline
- Long sleeves
- Leopard print
- Cropped hem
- Lower back keyhole with tie back detail
- Mesh fabric
- Form hugging fit
Style Number/Barcode: 06001-3087
Category Name: Night Out
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Linked to Style Chainlink Crop Top
Stay linked in with a stylish crop top! The top features a sleeveless cowl neckline, a chain-link pattern, spaghetti straps, and a cropped hem. The back features a bold open back with a strappy design and a mini O-Ring at the center. Complete look high waist jeans.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Cropped hem
- Chainlink pattern
- Strappy back
- Mini O-Ring
- Form hugging fit, runs true to size
Style Number/Barcode: 06001-3547
Category Name: Night Out
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Watchlist Faux Leather PVC Heels
Step onto the watchlist with stylish heels that take your look to the next level! The heels feature a closed-back, lace-up ties, an open square toe with a clear PVC strap, and a block heel. The heels are composed of a faux leather material. Complete look with an off-the-shoulder mini dress and dainty rings.
Fit & Features
- Closed-back
- Lace-up ties
- Open square toe
- Clear strap over toe
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3266
Category Name: Night Out
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Showstopper Mini Dress
You'll be such a showstopper in this sassy-chic mini dress. It features an on-trend mock neckline, long sleeves, side ruched detailing with an adjustable tie, and a short, curve-hugging fit. The lightweight stretchy knit fabric showcases a fab all-over snake print. Style this dress with black thigh-high boots.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Side ruching, adjustable drawstring at the hem
- Mini-length, form-fitting silhouette
- Stretchy knit fabric, snake print
- Runs true to size
Style Number/Barcode: 05102-4215
Category Name: Night Out
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sophisticated Glamour Glitter Blazer
Ring in the new year with a blazer that brings sophisticated glamour! It features a lapel collar, shoulder pads, long sleeves, a button-front closure, and a mid-length, relaxed fit. The glitter woven fabric features a stretchy satin-knit lining. Layer this blazer over a chic bustier and a form-hugging mini skirt.
Fit & Features
- Lapel collar
- Shoulder pads, long sleeves
- Single button-front closure, textured detail
- Dual front pockets
- Mid-length, relaxed fit
- Glitter woven fabric, satin-knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-1117
Category Name: Night Out
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Date Night Chic Floral Maxi Dress
You'll be totally chic for date night in this floral maxi dress that brings the romantic vibes. It features a sleeveless cowl neckline, spaghetti straps that lead to a lace-up back design for a customized fit, and a fitted floor-length silhouette with a thigh-high front slit. Complete the look with cute mules.
Shop Midi Dress: Chic Romance Floral Midi Dress
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Open back, strappy lace-up design, tie closure
- Floor-length fitted silhouette, high front slit
- All-over floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1443
Category Name: Night Out
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shrrr Of Myself Lace-Up Mesh Dress
Strut your bold and confident self to the club in this mesh mini dress featuring long sleeves, a plunge v-neckline with bungee lace-up straps, side ruched seams to accentuate your curves, and a bodycon fit. Complete the look with earrings and heels.
Fit & Features
- Long sleeves
- Plunge v-neckline, bungee lace-up straps
- Side ruched seams, back zipper and hook-eye closure
- Bodycon silhouette
- Mini-length hem
- Sheer mesh fabric, partial lining, moderate stretch
- Fits true to size
Style Number/Barcode: 05103-4695
Category Name: Night Out
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Queen Of The Gems Rhinestone Pearl Crop Top
Have a glamorous night looking like a queen in this mesh crop top featuring fitted long sleeves, a crew neck, and all-over rhinestones and faux pearl embellishments. Complete the look with matching bottoms and heels.
Shop Matching Bottoms: Queen Of The Gems Rhinestone Pearl Mini Skirt
Fit & Features
- Fitted long sleeves
- Crew neck
- Cropped hem
- All-over rhinestones and faux pearl embellishments
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4862
Category Name: Night Out
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple Desires Crepe Mini Dress
Have everyone eyeing you in this little black dress! It features a sleeveless square neckline, tank shoulder straps, a bodycon silhouette, and a mini-length hem on crepe fabric with a stretchy knit lining. Complete the look in statement heels and a clutch for a semi-formal party!
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Bodycon silhouette
- Mini-length hem
- Crepe fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2391
Category Name: Night Out
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get My Good Side Lace-Up Faux Leather Top
This faux leather top captures your good side for every post on social! It features a sleeveless one-shoulder neckline, a tank shoulder strap, a side ruched seam, and lace-up design, and a cropped hem. The top is composed of a faux leather fabric with a sewn-in knit lining. Complete the look in denim shorts for a trendy night out.
Fit & Features
- Sleeveless one-shoulder neckline
- Tank shoulder strap
- Side ruched seam, side lace-up design
- Cropped hem
- Faux leather fabric, sewn-in knit lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4840
Category Name: Night Out
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale