Night Out

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.

  • Talk Back Abstract Print Mesh Crop Top

    Everyone will be talking about you in this abstract print mesh crop top! Designed with sheer short sleeves and a crew neck, a head-turning open back, accented with a lattice strap, brings a subtle edge. Made with lightweight mesh fabric, the fitted crop hem and abstract print make a bold statement! Complete the look in a midi skirt.

    Fit & Features

    • Abstract print, mesh fabric lined with brushed knit
    • Open back with lattice strap
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5272

    Category Name: Night Out

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Fabulous Cat-Eye Sunglasses

    These sleek cat-eye sunglasses will be forever fab and always on-trend! They feature a chic oversized cat-eye design crafted with a plastic frame and arms, built-in nose pads for support, and tinted lenses. Style these shades with hoop earrings.

    Fit & Features

    • Oversized cat-eye design
    • Plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1070

    Category Name: Night Out

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Vibe Rhinestone Star Clear Shield Sunglasses

    Channel that iconic early 2000s vibe with these fabulous clear shield sunglasses! They feature a wide shield design with a flat top, sleek metal and plastic arms with trendy cutout detailing, mini rhinestones and star accents at each side, rubber nose pads, and clear lenses. Style with hoop earrings and a mini handbag.

    Fit & Features

    • Shield design with flat top
    • Metal and plastic arms, cutout detail
    • Mini rhinestones, star detail
    • Metal nose bridge, rubber nose pads
    • Clear lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1078

    Category Name: Night Out

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Sleek Square-Frame Sunglasses

    Accessorize your fave 'fits with these square-frame sunglasses for a sleek and chic vibe. The sunnies feature a classic square-shaped design with a plastic frame and arms, built-in nose pads, and tinted lenses. Style with hoop earrings.

    Fit & Features

    • Square-shaped design
    • Plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1076

    Category Name: Night Out

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Glitz One-Shoulder Glitter Mini Dress

    Bring the glitz and glam to your fabulous night out in this glitter mini dress! Designed with a stretchy glitter knit fabric, this mini-length dress is shaped with an asymmetric one-shoulder neckline with a long balloon-style sleeve to add that bold flair. The bodycon silhouette is accented with a ruched side design with an adjustable tie to accentuate your curves. Complete the look with metallic heels for a birthday or bachelorette party!

    Fit & Features

    • Stretchy glitter knit fabric
    • One-shoulder neckline
    • Long balloon sleeve with tapered hem
    • Ruched side design with adjustable tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5502

    Category Name: Night Out

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Allure Abstract Print Mesh Mini Dress

    Entice them with an artsy allure in this sultry abstract print mini dress! The airy sheer mesh fabric is accented with an abstract swirl print pattern for that trendy girl vibe, and includes a knit lining for coverage. The mini-length dress features a sleeveless square neckline with ruching at the bust, adjustable spaghetti straps for a customized fit, a side slit with sleek O-ring accents, and a flirty A-line silhouette. Style with stiletto heels for a rooftop bar!

    Fit & Features

    • Abstract swirl print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • Square neckline, ruched bust
    • Adjustable spaghetti straps
    • Side slit, O-ring accents
    • Lettuce-edge hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05103-5607

    Category Name: Night Out

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Polished Strapless Bow Ponte Mini Dress

    Go from brunch downtown to evening cocktails in this perfectly polished ponte mini dress! Featuring a strapless neckline and front cutout with playful bows, this bodycon dress exudes confidence while the mini-length hem and shorts lining provide both style and comfort. Complete the look with a mini handbag and heels.

    Fit & Features

    • Ponte fabric, stretchy knit shorts lining
    • Strapless neckline
    • Back zipper closure
    • Front cutout with bows
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5605

    Category Name: Night Out

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Aura Off-The-Shoulder Lace Crop Top

    You'll be putting off a sultry aura in this lace crop top perfect for flaunting all over town! This top features sheer fitted long sleeves, a folded off-the-shoulder neckline, and a sheer fitted crop hem made from delicate lace fabric. Complete the look in high-rise denim shorts or jeans for day and night fun!

    Fit & Features

    • Lace fabric, minimal stretch
    • Off-the-shoulder neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5261

    Category Name: Night Out

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Arrival Floral Trim Knit Mini Skirt

    Bring the flirtatious vibes when you arrive at the party in this sweet floral trim mini skirt! The stretchy knit fabric showcases a stunning sheen to catch everyone's eye. The skirt is shaped with a high-rise elasticized waist for added strap, a ruched seam with a dainty floral embroidered applique trim, and a short front slit. The bodycon fit on the mini-length silhouette will create a snatched look. Complete your fab look with the matching crop top!

    Shop Matching Top: Flirty Arrival Floral Trim Knit Crop Top

    Fit & Features

    • Stretchy knit fabric with sheen
    • High-rise elasticized waist
    • Ruched seam, floral embroidered applique trim
    • Short front slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1027

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Arrival Floral Trim Knit Crop Top

    Bring the flirtatious vibes when you arrive at the party in this sweet floral trim crop top! The stretchy knit fabric showcases a stunning sheen to catch everyone's eye. The top is shaped with a sleeveless sweetheart neckline with ruching at the bust, spaghetti straps, and dainty floral embroidered applique trim on the neckline and straps. The fitted cropped hem will give you that snatched look. Complete your fab look with the matching mini skirt!

    Shop Matching Bottoms: Flirty Arrival Floral Trim Knit Mini Skirt

    Fit & Features

    • Stretchy knit fabric with sheen
    • Sweetheart neckline
    • Ruched bust
    • Spaghetti straps
    • Floral embroidered applique trim
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5260

    Category Name: Night Out

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkly Catch Sleeveless Sequin Fishnet Mini Dress

    Looks like you've caught something sparkly...this fishnet mini dress! It features a scoop neckline with a string tassel tie, shoulder straps, a low scoop back, a form-hugging fit, and flirty side slits along the mini-length hem. Complete the look with platform heels for a party!

    Fit & Features

    • Sequin embellished fishnet fabric lined with mesh
    • Scoop neckline with string tassel tie
    • Shoulder straps
    • Low scoop back
    • Form-hugging fit
    • Side slit accents
    • Runs true to size

    Style Number/Barcode: 05103-5606

    Category Name: Night Out

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charm Me Puff Sleeve Lace Crop Top

    A date night or festival must have! This charming lace crop top shows off your adorable figure with puff short sleeves, a sweetheart neckline, button front closures, and a cropped hem with slit detail. The sheer lace fabric adds a touch of romance to your bold and adventurous look. Complete the look in a mini skirt. 

    Fit & Features

    • Sheer lace fabric, bust lining
    • Dual front button closures
    • Cropped hem with center slit
    • Runs true to size

    Style Number/Barcode: 06001-5256

    Category Name: Night Out

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Satin Sling-Back Stiletto Heels

    The satin stiletto heels feature a smooth satin material designed with an open square-shaped toe, a chic sling-back strap design, and a short stiletto heel for comfortable wear. Style with a sleek shoulder bag.

    Fit & Features

    • 2" Stiletto heel
    • Satin material
    • Open square toe
    • Toe strap
    • Sling-back strap design
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-4913

    Category Name: Night Out

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Versatile Dream Strappy Faux Leather Block Heels

    A versatile pair of faux leather heels that can be styled with multiple outfits! They feature a sleek square toe, block heel, and a strappy design for a stylish touch. Complete the look with a trendy tote bag.

    Fit & Features

    • 3.5" Block heel
    • Square toe
    • Strappy design
    • Faux leather material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4904

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Steal The Spotlight Rhinestone Metallic Stiletto Heels

    These metallic stiletto heels are sure to steal the spotlight! The almond toe provides a sleek and flattering fit, while the rhinestone strappy design and dual ankle straps with buckle closures add a touch of glamour. Complete the look with a chic clutch for a dressy event.

    Fit & Features

    • 4" Stiletto Heel
    • Almond toe
    • Rhinestone strappy design
    • Rhinestone dual ankle straps, buckle closures
    • Metallic faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4916

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetter Energy Asymmetric Wedge Heels

    Radiate trendsetter energy and turn heads your next night out in these fabulous asymmetric wedge heels! Made with shiny patent faux leather, they feature an open square-shaped toe with a strap, a thin adjustable ankle strap with a buckle closure, a closed back, and an angled wedge heel. Style with a little black dress and rhinestone fringe earrings!

    Fit & Features

    • Asymmetric wedge heel
    • Patent faux leather upper
    • Open square toe
    • Toe strap
    • Adjustable ankle strap with buckle closure
    • Closed back
    • Runs true to size

    Style Number/Barcode: 07401-4921

    Category Name: Night Out

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty As A Bow Long Sleeve Mesh Crop Top

    You'll look and feel so pretty in this statement mesh crop out for going out! The fitted long sleeves feature alluring keyhole cutouts adorned with delicate satin bows, while the square neckline is accentuated with another satin bow. The fitted crop hem and sheer mesh fabric add a sultry touch! Complete the look with a bralette and jeans.

    Fit & Features

    • Sheer mesh fabric, stretchy
    • Square neckline
    • Keyhole cutouts, satin bows
    • Fitted crop length
    • Style runs small

    Style Number/Barcode: 06001-5251

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Daydream Off-The-Shoulder Mesh Top

    This breezy floral mesh off-the-shoulder top will have you looking like a daydream! The airy sheer mesh fabric is accented with a soft floral print and includes a knit lining at the bust for coverage. The off-the-shoulder sweetheart neckline plays into the feminine look, featuring ruching at the bust and long fitted sleeves. The mid-length hem has a center front slit to add that flirty touch. Style this adorable top with light-wash jeans and mules!

    Fit & Features

    • Stretchy sheer mesh fabric, knit lining at the bust
    • Floral print
    • Off-the-shoulder sweetheart neckline, ruching
    • Long fitted sleeves
    • Center front slit
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-5248

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Flirtation Strapless Lace-Up Corset Mini Dress

    You'll be getting all the cuties in this perfect lace corset mini dress! The strapless neckline and flexible boning accentuate your curves, while the lace-up back and side ruched seams add a touch of allure. Made from soft lace fabric, this bodycon dress will hug your body in all the right places. Complete the look in stiletto heels for a dressy evening out!

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Strapless neckline
    • Lace-up back, zipper and hook-eye closure
    • Flexible boning
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3370

    Category Name: Night Out

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Essential Pointed Toe Rhinestone Stiletto Heels

    These rhinestone stiletto heels are a glam essential for any shoe lover's closet! They feature a sleek pointed toe, sparkling rhinestone embellished asymmetrical straps, an adjustable ankle strap, and buckle closure. Complete the look with a luxe clutch purse.

    Fit & Features

    • 4" Stiletto heel
    • Pointed toe
    • Rhinestone embellished asymmetrical straps
    • Adjustable ankle strap, buckle closure
    • Black color is faux leather, pink is metallic
    • Runs true to size

    Style Number/Barcode: 07401-4911

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Finesse Knit Bow Stiletto Heels

    Elevate your adorable finesse in these stiletto heels for a sweet look! The square toe and knit strap with bow inset provide a unique and stylish look, a stiletto heel and cushioned insole offer comfort. Complete the look with a trendy tote bag.

    Fit & Features

    • 4" Stiletto Heel
    • Square toe
    • Knit strap with bow inset
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4917

    Category Name: Night Out

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fab Statement Twist Strap Metallic Stiletto Mules

    Make a fabulous statement at your next party in these iconic metallic stiletto mules! Designed with a faux leather material, they feature an open square-shaped toe, a wide woven toe strap with a trendy twisted design, an open back for effortless on-and-off styling, and a short stiletto heel. Style with rhinestone fringe earrings.

    Fit & Features

    • 3.5" Stiletto heel
    • Faux leather upper, metallic sheen
    • Open square toe
    • Woven toe strap with twisted design
    • Open back, on-and-off styling
    • Padded insole
    • Runs true to size

    Style Number/Barcode: 07401-4912

    Category Name: Night Out

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Enchantment Organza Flower Metallic Heels

    These stunning metallic heels will have you in a glam enchantment! Designed with a glitzy chrome sheen, they feature an open almond-shaped toe, a dual toe strap design embellished with mini rhinestones, and a large organza flower accent with a center rhinestone knotted detail. The adjustable ankle and heel straps are adorned with matching rhinestones and feature a buckle closure, leading to a sleek stiletto heel. Style with rhinestone fringe earrings for a gorgeous formal look.

    Fit & Features

    • 3.5" Stiletto heel
    • Metallic faux leather upper
    • Open almond toe
    • Dual toe strap design, rhinestones, organza flower accent
    • Adjustable ankle and heel straps with rhinestones and buckle closure
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-4907

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let's Get Away Open Back Sleeveless Crop Top

    This sleeveless crop top is exactly what you need for a casual vacay or weekend look! Made with double-lined brushed knit fabric, this top is both soft and durable. The square neckline and open-back twist design create a trendy look, while the fitted crop hem provides a flattering silhouette. Complete the look in jean shorts and sandals!

    Fit & Features

    • Double-lined brushed knit stretchy fabric
    • Twist open back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5250

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale