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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Fierce And Fashionable Crop Top
Define your look as fierce and fashionable with this trendy printed crop top perfect for transtioning to fall! It features long balloon sleeves with elastic cuffed hems, a V neckline created by a tie front detail, and a cropped hem. The top is composed of a lightweight, airy woven fabric with no stretch.Style Number/Barcode: 06003-0326
Category Name: Night Out
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mirror Shine Metallic Mini Dress
Bring the shine to go with your gorge highlight girl! The mini dress features a sleeveless bodice, a square neckline, bungee shoulder straps and a mini length silhouette. Dress is composed of a lined metallic knit fabric that offers a form hugging fit with a slight stretch. Includes a back zipper closure.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0302
Category Name: Night Out
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Twinkle On Rhinestone Anklet
Add a little twinkle to that ankle! We are loving the idea of a blinged out anklet accompanying your blinged out heels! Designed with flat chain links that are encrusted with rhinestones, and an adjustable lobster clasp closure.Style Number/Barcode: 07003-0036
Category Name: Night Out
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pleat Me Tonight Asymmetrical Mini Dress
Just the way you like it. This sexy mini dress features a plunging V neckline, adjustable spaghetti straps, a wrap-like skirt with pleated accents, and an asymmetrical hemline. Crepe knit fabric offers a form hugging fit with plenty of stretch.
Fit & Features
- Sleeveless, adjustable spaghetti straps
- Plunge, v-neckline, wire inserts for structure
- Wrap-like skirt, pleat accents
- Asymmetrical short-length hem
- Crepe knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05103-0428
Category Name: Night Out
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mini Rhinestone Drawstring Purse
Bring the glamour with this glitzy embellished purse! It features a mini drawstring pouch design, a rhinestone handle, and rhinestone accents throughout. Purse is composed of a mesh material and has a knit lining.
Style Number/Barcode: 07204-0055
Category Name: Night Out
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Scalloped Lace Trumpet Midi Dress
Bring the flare with this flirty midi dress! It features a sleeveless bodice, a plunging V neckline with scalloped lace trim, adjustable straps that cross at the back and a midi length silhouette with a flared trumpet hem. Dress is composed of a lined lace fabric that offers a relaxed fit with minimal stretch. Includes a back zipper closure.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-0304
Category Name: Night Out
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cross Back Detail Midi Dress
Strappy and stunning, this cross back midi dress is not so basic. It features a sleeveless bodice, tank-like shoulder straps, a square neckline, flaterring slanted seams along the bust, a lattice back, and a mid-length, form hugging fit. The dress is composed of a ponte knit fabric with moderate stretch.Style Number/Barcode: 05103-0427
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Rhinestone Bangle Bracelet
You are ever so sleek and ever so polished bae. This bracelet is designed with a hinge closure, a thin and dainty design and rhinestones encrusted throughout.Style Number/Barcode: 07003-0035
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Show Me Romance Satin Romper
Show off your romantic side with a feminine romper!
This garment features a v-neckline, and spaghetti straps that are adjustable and lead to a bow tie back detail. Bodice of this style shows a knot design with a keyhole cut out detail that adds a sweet touch! Lower back keyhole cut out that has an elasticity, and a hem that hits mid thigh. It is composed of a satin like material that offers a relaxed fit with no stretch. Front of romper is fully lined.
Style Number/Barcode: 06503-0062
Category Name: Night Out
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rose Charm Necklace Set
Glam up in 1, 2, 3 seconds! This 3-piece necklace set features one choker, one chain and one charm necklace for layering or wearing alone. Topped with lobster clasp closures for easy on and off.Style Number/Barcode: 07002-0104
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rainbow Fringe Earrings
Chase the rainbow in these fabulous earrings! Cascading down with a rainbow rhinestone fringe, they are the star of the show! Earrings have a post back closure.Style Number/Barcode: 07001-0144
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut Out The Drama Midi Dress
Cut out all that drama and slay in this sultry midi dress! It features a sleeveless bodice, a square neckline, tank-like shoulder straps, a center and side waist cut out with a horizontal bar accent, and a mid-length, form hugging fit. Dress is composed of a stretchy knit fabric with a pretty sheen.Style Number/Barcode: 05101-0301
Category Name: Night Out
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lit In Lurex Midi Dress
Light it up in this gorgeous Lurex midi! Dress has a body con cut and features multi-color, vertical Lurex striping, an off-the-shoulder neckline, a deep V with wire boning at bust, and long sleeves. Dress fully lined, slips on, and is made from a woven nylon blend with moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size
Style Number/Barcode: 05101-0217
Category Name: Night Out
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Marquise Stone Statement Earrings
Add a little style to a simple updo with a pair of beautiful statement earrings! These stunners feature a feathered out clustered style of multi sized marquise stones. Earrings have a post back closure.Style Number/Barcode: 07001-0145
Category Name: Night Out
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rhinestone Waist Cut Out Mini Dress
Cut out all the old styles from your closet and stun in this rhinestone waist mini! The dress features a sleeveless bodice, adjustable spaghetti straps, a square neck and back, a sultry front waist cut out with a rhinestone adorned vertical bar accent, and a short, curve hugging fit. Dress is composed of a jersey knit fabric with plenty of stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0300
Category Name: Night Out
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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One Sleeve Satin Midi Dress
Keep it stunning in sophisticated satin! Dress features a one shoulder neckline, a fitted long sleeve, princess seams at the bust and a midi length silhouette. Dress is composed of a lined satin-like fabric that offers a form hugging fit with a slight stretch. Includes a back zipper closure with hook and eye closure.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0299
Category Name: Night Out
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Quilted O-Ring Door Knocker Earrings
We are obsessed with door knocker earrings! Their versatility adds style to all looks whether casual or formal. Designed with a post back bar that leads into a hanging o-ring. Earrings feature a quilted textured pattern.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0208
Category Name: Night Out
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mesh Burnout Jumpsuit
You'll be a vision of elegance and grace in this classy jumpsuit!
Fits & Features
- Semi-Sheer Mesh Top With Flocked Velvet Prints Throughout
- Crew Neckline
- Fitted Long Sleeves
- Button Closure At Nape Of Neck I Cut Out At Center Back
- High Rise Waist
- Tapered Crepe Pant Legs
- Offers Moderate Stretch
Style Number/Barcode: 06502-0159
Category Name: Night Out
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sarina High Slit Sequin Midi Dress
Special Occasion
Highlight your beauty with our mesmerizing Sarina dress! You'll illuminate every room!
Fits & Features
- Bungee Shoulder Straps Leads To Racerback Design With Zip Closure
- Plunging V Neckline
- Slim Fit Bodice
- Midi Length Silhouette With Thigh-High Slit
- Fully Lined Mesh Fabric With Sequins Throughout
- Curve-Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0264
Category Name: Night Out
Price: $19.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Arielle Geometric Sequin Midi Dress
Special Occasion
Shine at all your soirees in our gorgeous Arielle midi dress!
Fits & Features
- Plunging V Neckline
- Adjustable Spaghetti Straps That Lace Up At The Back
- Midi Length Silhouette With Thigh High Slit
- Mesh Lined Fabric With Shimmering Geometric Sequins Throughout
- Fully Lined
- Curve-Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0266
Category Name: Night Out
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Nadine Formal Sequin Midi Dress
Special Occasion
Stand out in sequins as you wow them all in our Nadine sequin dress!
Fit & Features
- V-Neckline I Padded Cups
- Spaghetti Straps
- Midi Length Silhouette With Split At Center Back
- Lined Mesh Fabric With Sequins Throughout
- Form-Hugging Fit
- 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: 05001-0265
Category Name: Night Out
Price: $20.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rowena Formal Heat Stone Mini Dress
Special Occasion
Sparkle up the night like the goddess you are in our shimmering Rowena dress! Her heat stones will add a sparkle to your glow!
Fit & Features
- V- Neckline
- Adjustable Spaghetti Straps
- Gemstones
- Heat Stones
- Geometric
- Fully Lined Mesh
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 05103-0423
Category Name: Night Out
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kayley Sequin Midi Dress
Special Occasion
Have a night to remember in our Kayley! She features a wired deep v neckline, double adjustable spaghetti straps that lead to a criss-cross back, padded cups, and a fully lined form-fitting silhouette that offers a moderate stretch. She has a zipper located center back and is composed of a mesh material that is adorned in sequins! Her hem hits mid-length and she features a small slit at the back. Complete look with a sleek clutch.
Fit & Features
- Wired V-neckline with padded cups
- Double row adjustable spaghetti straps
- Criss-cross back
- Sequins
- Midi length silhouette with small center slit at the back
- Fully lined mesh fabric
- Form hugging fit, moderate stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0262
Category Name: Night Out
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me Out Pencil Midi Skirt
We are going to take you out on a hot date, because your outfit is F-I-R-E ! This midi skirt is designed with all the curve flattering details that we love. A high waistline, a curve hugging silhouette, and a high thigh slit. Hem hits passed the knee, and midi is composed of a woven knit material that offers moderate stretch. Zipper located mid back.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06401-0070
Category Name: Night Out
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance