Night Out

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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.

  • Hawt V-Neck Ribbed Sweater Dress

    The temps may be dropping but you'll raise them in this sweater dress! It features a sleeveless, spaghetti strap design, v-neck, and a fitted, mini-length hem. Complete the look with the matching top.

    Shop The Matching Top: Hawt Crop Ribbed Sweater Top

    Fit & Features

    • Sleeveless, spaghetti straps
    • V-neck
    • fitted, mini-length hem
    • Rib-knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1042

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Flirt Cutout Tie Mini Dress

    Give them just a peek of your sultry self in this mini dress for a major club night! It features a sleeveless V-neckline, spaghetti straps, an underbust seam, and a cutout waist with a tie-back closure along the bodycon silhouette. Complete the look in this mini-length dress with large hoop earrings.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Underbust seam
    • Cutout waist, tie-back closure
    • Bodycon silhouette
    • Mini-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4629

    Category Name: Night Out

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Glow Getter Rhinestone Stiletto Heels

    Chase that glow with heels that sparkle up your night! The heels feature lace-up straps, an open square toe with a single strap over the toe, and a rhinestone embellished stiletto heel. Complete look with an LBD

    Fit & Features

    • Lace-up straps
    • Open square toe with a single strap over the toe
    • Rhinestone embellished stiletto heel 
    • Faux suede material

     

    Style Number/Barcode: 07401-2786

    Category Name: Night Out

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drop the Sparkle Rhinestone Bustier

    Made for the girl who doesn’t wait for the disco ball to shine. This bustier top drips in rhinestone fringe with a curve-hugging fit that’s ready for nights out, concerts, or your birthday slay.

    Fit & Features

    • Sleek woven fabric
    • Adjustable spaghetti straps
    • Sweetheart neckline with rhinestone fringe trim
    • Built-in padded underwire bust
    • Multiple back hook and eye fasteners
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000112

    Category Name: Night Out

    Price: $46.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strap Up Square Toe Block Heels

    Strap up and step out in style! These square toe block heels will catch a lot of eyes. They feature a multi-strap design with an ankle buckle closure on faux leather material. Complete the look in trendy jeans.

    Fit & Features

    • Square toe
    • Block heel
    • Multi-strap design
    • Adjustable ankle buckle closure
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-3883

    Category Name: Night Out

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Inspired Charm Strapless Watercolor Print Mini Dress

    Envoke an inspired charm in this watercolor print mini dress and capture attention at parties or casual dinners!  With its strapless straight-across neckline and bodycon silhouette, this mini dress will accentuate your curves and flatter your figure. Made from airy lined mesh fabric with an eye-catching watercolor print, this dress is a must-have for any fashion-forward girlie! Complete the look in stiletto heels and a purse!

    Fit & Features

    • Watercolor print
    • Mesh fabric lined with stretchy knit
    • Strapless straight neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5605

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Sultry And Stunning Mini Dress

    You'll look simply sultry and stunning in this lightweight knit mini dress! It features a strappy cross-front design with a V-neckline, long fitted sleeves, an open back with a strappy cross-back design, and a short, curve-hugging fit. Style this dress with clear mules.

    Fit & Features

    • Front and back cross-strap designs
    • V-neckline
    • Open back
    • Long fitted sleeves
    • Mini-length, form-fitting silhouette
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4289

    Category Name: Night Out

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Metallic Marvel Sleeveless Mini Dress

    Make them marvel in awe of your stunning style with a mini dress that wows! This pretty stunner features a sleeveless cowl neckline, spaghetti straps, and a mini-length hem. The dress is composed of a lined metallic knit fabric that offers a bodycon fit with a moderate stretch. Complete look with clear heels and rhinestone hoops

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Mini length hem 
    • Lined metallic knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05103-4263

    Category Name: Night Out

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Chic Over-The-Knee Boots

    These fitted over-the-knee boots are so effortlessly chic. They feature an almond-shaped toe, a block heel, and an inner zipper closure. The boots are composed of a half faux suede and half stretchy knit composition. Style with a sweater dress and a trendy boater hat.

    Fit & Features

    • Over-the-knee fitted design
    • Almond-shaped toe
    • Block heel
    • Partial inner zipper closure
    • Half faux suede and half stretchy knit composition
    • Runs true to size

    Style Number/Barcode: 07402-0812

    Category Name: Night Out

    Price: $12.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sophiscated Chic Belted Jumpsuit

    Sophisticated and chic, this belted jumpsuit will elevate your date night look. It features a strapless sweetheart neckline with a fitted bodice, a high-rise belted waist, and skinny pant legs. The smooth woven fabric offers a moderate stretch. Style with hoop earrings and strappy heels.

    Fit & Features

    • Strapless sweetheart neckline
    • Fitted bodice, back zipper, hook and eye closure
    • High-rise belted waist, side pockets
    • Skinny pant legs, form-hugging fit
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06402-0630

    Category Name: Night Out

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Encircled In Luxe Rhinestone Earrings

    Embrace the luxe life with these sparkling earrings! The earrings feature a rhinestone embellished circular outline post with an embellished rectangular outline attached. Complete look with a satin mini dress and heels.

    Fit & Features

    • Circular outline design on post
    • Rectangular outline attached
    • Mini rhinestone embellishment
    • Post-back closure


    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0906

    Category Name: Night Out

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Zadie Formal Sequin Bodycon

    Special Occasion

    Make a sparkling entrance with a formal bodycon that slays your look! Zadie features a sleeveless scoop neckline, bungee spaghetti straps, a sequin embellished body, and a ruched drawstring at the hem. The dress is composed of a lined mesh fabric that offers a form-hugging fit. Complete look with rhinestone heels.

    Fit & Features

    • Sleeveless scoop neckline
    • Bungee spaghetti straps
    • Sequins
    • Ruched drawstring at hem
    • Mini-length silhouette
    • Lined mesh fabric, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05001-0748

    Category Name: Night Out

    Price: $14.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sammy Formal Crepe Cutout Midi Dress

    Special Occasion

    For looking sultry and sleek! Sammy is a class act and full of surprise in her sleeveless crew neck style with front and side sultry cutouts and a chic wrap-style bodice. Her curve-hugging silhouette ends below the knee to elongate your figure while the back slit accent adds extra detail. The formal dress is composed of a crepe texture knit fabric with a moderate stretch. Finish the look in stiletto heels and a rhinestone bracelet.

    Fit & Features

    • Sleeveless, crew neck, bra-friendly
    • Front cut bust and side cutout
    • Back zipper closure, slit accent
    • Wrap-style bodice
    • Form-fitting silhouette
    • Midi-length hem
    • Crepe texture knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-0898

    Category Name: Night Out

    Price: $29.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Floral Knit Mini Dress

    Showcase a sweet style in this adorable floral print mini dress. It features a sleeveless cowl neckline, spaghetti straps, a short, curve-hugging fit, and an all-over floral print pattern. Style with hoop earrings and cute mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Floral print
    • Knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1514

    Category Name: Night Out

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Skip A Beat Criss Cross Halter Top

    Your heart will skip a beat for this halter top! Featuring a sleeveless, criss-cross strap bodice with a keyhole accent, fitted crop hem, and an open-back design on stretchy rib-knit fabric. Complete the look in boyfriend jeans.

    Fit & Features

    • Sleeveless, halter neckline
    • Criss-cross straps
    • Keyhole accent
    • Fitted crop hem
    • Open-back design
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4208

    Category Name: Night Out

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Style Ruched Mesh Midi Dress

    Show off your iconic style in this alluring and chic mesh midi dress. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a ruched overlay at the waist, ruching down the side seams, and a midi-length, curve-hugging silhouette. The sheer mesh fabric includes a full knit lining. Complete the look with clear lucite heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Ruched overlay at the waist
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1681

    Category Name: Night Out

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Sophistication Satin Crop Top

    Bring the sophistication and stun them all in this mesmerizing top! It features an elastic off the shoulder neckline, long flowy sleeves and a cropped hem. Top is composed of a satin-like fabric that offers a relaxed fit with a minimal stretch.

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

    Style Number/Barcode: 06003-0462

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off The Shoulder Ruched Dotted Mini Dress

    Bring the charm in a dotted mini dress to make a flirty impression. The dress features an off the shoulder neckline, sheer long sleeves with a swiss dot pattern and a ruched silhouette throughout. Complete your date night ready look with extra-large hoops and sleek stilettos

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust with tie front accent
    • Long sheer sleeves with swiss dot pattern
    • Ruched body
    • Mini length silhouette
    • Form hugging fit

     

    Blue: Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.

    Blush: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0801

    Category Name: Night Out

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Glam Faux Leather Bodysuit

    Channel an edgy glam look with a halter that makes a bold impression! The bodysuit features a halter neck, a chunk chain-link halter strap, and a thong bottom with dual snap-button closure. The bodysuit is composed of a lined faux leather fabric that offers a form hugging fit with a moderate stretch. Complete look with faux leather pants and mules.

    Fit & Features

    • Halter neck
    • Chunky chain-link halter strap
    • Thong bottom
    • Dual snap button closure
    • Lined faux leather fabric
    • Form hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3809

    Category Name: Night Out

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Certified Scene Stealer Rhinestone Chainmail Top

    Britney would wear it, and honestly? So should you. With its slinky drape and open back, this rhinestone chainmail is a whole performance. Perfect for concerts, girls' nights, or parties when you want to shine!

    Fit & Features

    • Rhinestone chainmail, metallic knit lining
    • Halter V-neckline, spaghetti strap tie
    • Open back with spaghetti strap tie
    • Hanky cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000115

    Category Name: Night Out

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Iconic Elegance Off The Shoulder Jumpsuit

    Channel iconic elegance with a sleek jumpsuit! The jumpsuit features an off-the-shoulder neckline, a tiered ruffled popover accent, short sleeves, and a straight leg fit with a flared hem. Complete look with wedges and hoops. 

    Fit & Features

    • Off the shoulder neckline
    • Tiered ruffled popover
    • Short sleeves
    • Straight leg, flared hem
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06502-0591

    Category Name: Night Out

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walking Knit Style Block Booties

    Take stylish steps in these block heel booties featuring an on-trend pointed toe, partial knit and faux leather material, and an above-the-ankle length. Complete the look in a chic blazer.

    Fit & Features

    • Pointed toe 
    • Block heel
    • Above-the-ankle length
    • Partial knit and faux leather material
    • Pull-on/off styling
    • Runs true to size

    Style Number/Barcode: 07403-1611

    Category Name: Night Out

    Price: $12.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rad And Retro Under The Knee Boots

    Totally rad and retro, you'll be one edgy chick in these fab under-the-knee boots featuring an almond toe, chunky platform sole and block heel, and side zipper closure, and are composed of faux leather material. Complete the look in a printed mini-dress for a party!

    Fit & Features

    • Almond toe
    • Chunky platform sole and block heel
    • Side zipper closure
    • Under-the-knee length
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0865

    Category Name: Night Out

    Price: $28.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance