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.

  • Love To Shine Sequin Crop Top

    A girl's gotta shine and you'll love this sequin crop top for shimmering at every party! The top features a sleeveless, one-shoulder neckline with a strap and side tie along the hem. Complete the look with the matching skirt.

    Shop Matching Skirt: Love To Shine Sequin Mini Skirt

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • One shoulder strap
    • Side tie
    • Cropped hem
    • Sequin-knit fabric, lined
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06003-2062

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Set In Satin Crop Corset Top

    Set the mood for the night in this sultry satin corset top perfect for dinner and drinks! Featuring a sleeveless sweetheart neckline, detachable and adjustable spaghetti straps, a bra underwire bust, flexible boning, back hook, and eye closures, and a pointed front crop hem. The silky satin woven fabric includes a knit lining. Complete the look in a sleek mini skirt and heels!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Detachable and adjustable spaghetti straps
    • Bra underwire bust, flexible boning
    • Back hook and eye closures
    • Pointed front crop hem
    • Satin woven fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1984

    Category Name: Night Out

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Image Abstract Surplice Crop Top

    You'll love all the pics you take in this abstract print crop top that gives your outfit the perfect statement piece! It features flowy long sleeves with banded cuffs, a surplice V-neckline, and a banded crop hem on smooth knit fabric. Complete the look in sleek faux leather pants for an art show and dinner!

    Fit & Features

    • Flowy long sleeves, banded cuffs
    • Surplice V-neckline
    • Banded crop hem
    • Abstract print
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4859

    Category Name: Night Out

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Naturally A Classic Tweed Bustier

    Become an instant 90s-inspired classic in this tweed bustier to posh up your vibe! Featuring a sleeveless sweetheart neckline with non-slip grip lining, adjustable and detachable spaghetti straps so you style it strapless, a built-in padded underwire bust, a cropped hem with non-slip grip lining, and a stretchy knit back. Complete the look in a chic mini skirt and heels for a date night or party!

    Fit & Features

    • Sleeveless sweetheart neckline, non-slip grip lining
    • Adjustable and detachable spaghetti straps
    • Built-in padded and underwire bust
    • Cropped hem with non-slip grip lining
    • Tweed front design, stretchy knit back, multiple hook-eye closures
    • Runs true to size

    Style Number/Barcode: 06003-2194

    Category Name: Night Out

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dose Of Drama Satin Lace Corset Mini Dress

    Add romantic drama in the form of this satin mini dress! With delicate lace trim and a corset-fashioned waist, this chic style is destined to turn heads at parties and events. Featuring a sleeveless V-neckline with lace trim, adjustable spaghetti straps, flexible boning inserts along the waist with a lace-up corset overlay, a bodycon silhouette, and a lace trim mini-length hem. Complete the look in lace-up heels and jewelry.

    Fit & Features

    • Sleeveless V-neckline with lace trim
    • Adjustable spaghetti straps, back zipper and hook-eye closure
    • Flexible boning waist inserts, lace-up corset overlay
    • Bodycon silhouette
    • Lace trim mini-length hem
    • Silky satin woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2534

    Category Name: Night Out

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Standing Tall Satin Block Heel Pumps

    Stand tall with chic style in these satin pumps perfect for cocktail mixers or grabbing dinner downtown! The heels feature a closed pointed-toe, a block heel, a closed ankle with zipper closure, and dual adjustable ankle straps with buckle closure. Style the pumps with a posh blazer for the perfect finish to your look!

    Fit & Features

    • Closed pointed toe
    • Block heel
    • Closed ankle, zipper closure
    • Dual adjustable ankle straps, buckle closure
    • Smooth satin material
    • Runs true to size

    Style Number/Barcode: 07401-4576

    Category Name: Night Out

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drama In The Details Open Back Skater Mini Dress

    Start drama by serving major allure in this skater mini dress on your next night on the town! This dress features a plunging V-neckline with a sleek bar strap, a bold open back design, and a playful ruffled mini-length hem that moves with you.

    Fit & Features

    • Mesh-lined fabric
    • Plunge V-neckline with bar strap
    • Open back with strap
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000194

    Category Name: Night Out

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dramatic Blooms Rosette Rhinestone Thigh-High Boots

    Dare to bloom in the most dramatically chic way in these satin thigh-high stiletto boots! Perfect for strutting into parties, these boots feature a pointed toe, inner zipper closure, glitzy rhinestone, and rosette flower appliques, and a scrunched thigh-high shaft. Style with a bold mini dress.

    Fit & Features

    • Pointed toe
    • Inner zipper closure
    • Rhinestone and rosette flower appliques
    • Scrunched thigh-high shaft
    • Stiletto heel
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07402-0907

    Category Name: Night Out

    Price: $9.97 $80.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic For The Season Cable Knit Bolero

    This cozy cable knit bolero is a chic style pick for the season! It features long fitted sleeves, an open front, and a cropped hem. The cable knit fabric has an ultra-soft feel and offers plenty of stretch. Complete your look with the matching tube top and a faux leather mini skirt for a fab holiday party look.

    Shop Matching Top: Chic For The Season Cable Knit Tube Top

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Cropped hem
    • Ultra-soft cable knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1795

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Allure Faux Sheer O-Ring Tights

    Elevate your style and bring that trendy allure in these faux sheer O-ring tights! They feature a high-rise fit, a small gauge fishnet design with a chic double O-ring pattern, and a nude-tone complete lining for a faux sheer look to still keep you warm. Offers plenty of stretch. Pair with ankle booties!

    Fit & Features

    • High-rise fit
    • Small gauge fishnet design
    • Double O-ring pattern
    • Nude-tone lining, faux sheer look
    • Plenty of stretch


    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07306-0318

    Category Name: Night Out

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Things Up Rhinestone Elastic Hair Tie

    Glam up your hairstyles with this hair tie perfect for dressing up your look with a little glitz! Featuring a rhinestone embellished decoration attached to a stretchy elastic band to create all sorts of chic looks. Complete the look with a ring set for a semi-formal party!

    Fit & Features

    • Hair tie
    • Rhinestone embellished decoration
    • Stretchy elastic band

    Style Number/Barcode: 07006-0453

    Category Name: Night Out

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Allure Fringe Hem Open Back Crop Top

    Show off your flawless allure in this slinky knit fringe hem crop top! Designed with a sleek stretchy knit fabric with a fabulous sheen, this is the perfect going-out top for nights out with your squad. It features a sleeveless cowl neckline for that chic draped look, and bungee spaghetti straps that lead to a sultry open back with a cross-back strappy design. The angled cropped hem is accented with a ball-chain fringe for a trendy vibe. Style this form-hugging top with faux leather pants and clear heels.

    Fit & Features

    • Stretchy knit fabric with knit lining
    • Sleeveless cowl neckline
    • Bungee spaghetti straps
    • Open back, cross-back design, tie closure
    • Angled cropped hem with ball-chain fringe
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-4906

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer Fun Off-The-Shoulder Crop Chiffon Blouse

    You'll have the most fun in this cute chiffon crop blouse on a date night or evening out! The breezy sheer peasant long sleeves and off-the-shoulder neckline add a flirty touch, while the adjustable front ruched drawstring allows for a personalized fit. Complete the look in a sleek faux leather midi skirt and pointy toe heels for a chic allure!

    Fit & Features

    • Chiffon woven fabric
    • Off-the-shoulder
    • Front ruched drawstring
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2355

    Category Name: Night Out

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Got The Blues High Rise Denim Print Flare Pants

    Got the blues? Refresh your mood in these denim pants perfect for achieving a stylish look while staying comfy! They feature an elasticized high-rise waistband, a hip-hugging fit, and a flared hem on stretchy mesh fabric with a denim jean print. Complete the look in a basic tee for a concert!

    Fit & Features

    • Denim jean print, mesh fabric, stretchy
    • High-rise elasticized waistband
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2483

    Category Name: Night Out

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Captivating Lace Trim A-Line Satin Dress

    Even in the most crowded room, you'll be captivating in this satin dress on your next evening out! This delicate and femme dress boasts a romantic plunge V-neckline with lace trim and bust tie while the flattering A-line silhouette and short-length hem show off your curves. Complete the look in stiletto heels and a purse!

    Fit & Features

    • Satin fabric, slight stretch
    • Lace trim, bust tie
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5574

    Category Name: Night Out

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Cute Strapless Tie-Dye Bodycon Mini Dress

    Looking cute is easy with this tie-dye mini dress for summer! This mini-length dress will effortlessly enhance your curves and flatter your figure featuring a trendy strapless neckline and bodycon silhouette. Complete the look with earrings and heels for a party!

    Fit & Features

    • Tie-dye print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5782

    Category Name: Night Out

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rock Star Vibes Fringe Faux Leather Mini Skirt

    Showcase rock star vibes in this trendy fab faux leather mini skirt! It features a high-rise waist, a mini-length hem with flirty short fringe detailing, and a form-hugging silhouette. Style with a graphic tee and cowboy boots for festival season.

    Fit & Features

    • High-rise elasticized waist
    • Mini-length hem
    • Short fringe detailing
    • Form-hugging fit
    • Smooth faux leather fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06401-0569

    Category Name: Night Out

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glow Mode Activated Leopard Mini Dress

    Warning: may cause heart rates to rise. With a leopard abstract print, cutouts, and a dramatic slit, this dress is made for midnight entrances! 

    Fit & Features

    • Leopard abstract print, metallic knit fabric, mesh knit lining
    • Cowl halter neckline, spaghetti strap tie
    • Cutout bodice, hoop insert
    • Bodycon fit
    • Side ruffled trim slit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000171

    Category Name: Night Out

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sway Me Faux Leather Fringe Mini Skirt

    Don't let anyone sway you from wearing this faux leather mini skirt on repeat! It features a high-rise waist, bodycon silhouette, a side slit cutout with chain fringe trim, and a fitted hem. Complete the look in a sleeveless basic top and heels for a night out.

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Side slit cutout
    • Chain fringe trim
    • Mini-length hem
    • Faux leather fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0836

    Category Name: Night Out

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Slay Satin Mesh Drape Dress

    You'll be sweetly slaying the club in this satin mini dress! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a lightly padded bust, mesh draping across the bust, and a bodycon silhouette. Complete the look in a glam necklace and earrings set!

    Fit & Features

    • Sleeveless sweetheart neckline, adjustable spaghetti straps
    • Lightly padded bust, back zipper closure
    • Mesh draping across the bust
    • Bodycon silhouette
    • Mini-length hem
    • Smooth satin, lined, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05103-4724

    Category Name: Night Out

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Key Figure Mesh Crop Top

    Cheer for sheer in this sultry mesh crop! Team it with your favorite bra or bandeau and out you go! Top features a mock neck, long sleeves, and large crisscross wrap and keyhole detail at front. Top slips on and is made from a sheer mesh fabric with plenty of stretch.

    Style Number/Barcode: 06001-1467

    Category Name: Night Out

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Point Clear And Chrome Pump

    Your fashion sense is always on point! Let it show with these chic pumps! They feature a pointed toe and heel with clear plastic sides.

    Style Number/Barcode: 07401-0067

    Category Name: Night Out

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glitter Galore Midi Dress

    Slay all day in the Glitter Galore midi dress!

    Fits & Features

    • Sweetheart Neckline
    • Double Strap Hook & Eye Closure At Back
    • Cut-Out Details Along Sides And Back
    • Fully Lined, Glitter Knit Composition
    • Curve-Hugging Fit I Moderate Stretch
    • Zipper Not Included

     

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0294

    Category Name: Night Out

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Day N' Night Satin Bomber Jacket

    Slay all day and all night in a satin bomber! This lightweight jacket features a zippered front, long sleeves, square frontal pockets, and mid waist hem with ribbed detail. Jacket is composed of a silk blended fabric that offers a relaxed fit with little stretch. Fully lined with a chiffon like material. 

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0241

    Category Name: Night Out

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale