Evening Wear Boleros

Get ready to own the night with evening wear boleros that are about to become your ultimate style sidekick. Whether you're slipping into a sultry gown or rocking a chic cocktail dress, these boleros are the perfect finishing touch to elevate your look from fab to fierce. With just the right mix of elegance and edge, you'll be turning heads and breaking hearts without even trying. So, grab your heels and your favorite clutch—it's time to step out and shine like the star you are!

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Windsor All Class Faux Fur Shawl in Black

$26.90

A chic black faux fur shawl with satin-like lining and ribbon tie for elegant occasions.

Sheer Mesh Flared Sleeve Bolero in Black

$16.90

A black sheer mesh bolero with flared sleeves, perfect for prom or going out.

Sheer Mesh Blouson Sleeve Bolero in Black

$19.90

A chic black sheer mesh bolero with blouson sleeves, perfect for layering over any outfit.

Exclusive Chic Faux Fur Long Sleeve Bolero in Black

$39.90

An ultra-cropped black bolero with plush faux fur cuffs and collar on rib knit fabric.

Abundant Luxury Faux Pearl Bead Bolero in White

Best Seller

Abundant Luxury Faux Pearl Bead Bolero in White

$34.90

An elegant white mesh bolero adorned with faux pearls and beads, featuring flared slit cuffs.

Windsor Ms. Diva Faux Fur Shawl in Black

$26.90

A chic black faux fur shawl with a smooth lining and triple-row hook closure for formal events.

Into Fall Fur Shawl in Ivory

$26.90

An ivory faux fur shawl with a satin-like lining and optional hook-eye closure.

Layered Poise Long Sleeve Crepe Bolero in Ivory

$24.90

An ivory crepe bolero with fitted long sleeves and an open front for a polished look.

Feeling Breezy Crochet Bolero Sweater in Tan

$29.90

A sheer tan crochet bolero sweater featuring long flare sleeves and an ultra-cropped open front design.

Windsor Chic And Sheer Mesh Ruched Sleeve Bolero in Black

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Windsor Chic And Sheer Mesh Ruched Sleeve Bolero in Black

$16.90

A chic black sheer mesh bolero featuring long ruched sleeves and an ultra-cropped hem.

Whimsical Mood Bow Long Sleeve Mesh Bolero in Black

$19.90

A sheer black mesh bolero with bow-adorned sleeves and an ultra-cropped open front design.

Endless Glam Faux Fur Shawl in Ivory

$26.90

An elegant ivory faux fur shawl with a smooth nylon lining and a chic hook-and-eye closure.

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Windsor Sheer Mesh Flared Sleeve Bolero in White

$16.90

(27)

Windsor Sheer Mesh Flared Sleeve Bolero in White | Size: M | Mesh Fabric/Sheer Mesh Fabric Free Shipping on All Orders Over $75.

Exclusive Chic Faux Fur Long Sleeve Bolero in Black

$39.90

(20)

This bolero is the perfect piece for a sophisticated, exclusive look! Designed on smooth rib knit fabric, this is a fashion staple you'll adore featuring fitted long sleeves with plush faux fur cuffs and collar neckline, an open front design, and an ultra-cropped hem. Complete the look with a glitter clutch for a holiday party or black tie soiree! Fit & FeaturesFitted long sleeves, plush faux fur cuffs, Plush faux fur detachable collar neckline, Open front design, Ultra-cropped hem, Smooth rib knit fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Exclusive Chic Faux Fur Long Sleeve Bolero in Black | Size: XL | Knit Fabric

Sheer Mesh Blouson Sleeve Bolero in Black

$19.90

(15)

This chic sheer mesh bolero is a stylish layer to wear over your everyday looks or formal outfits! It features an open front, a majorly cropped hem, and long blouson sleeves with tapered hems. Pair this trendy layer with stud earrings. Fit & FeaturesOpen front, Cropped hem, Long blouson sleeves, tapered hems, Sheer mesh fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sheer Mesh Blouson Sleeve Bolero in Black | Size: S | Mesh Fabric/Sheer Mesh Fabric

Chic And Sheer Mesh Ruched Sleeve Bolero in Black

$16.90

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Layer on chic style with this airy sheer mesh bolero with long fitted sleeves with a trendy ruched design. Fit & FeaturesSheer mesh fabric, high stretch, Long fitted sleeves, ruched design, Ultra cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic And Sheer Mesh Ruched Sleeve Bolero in Black | Size: M | Mesh Fabric/Sheer Mesh Fabric

Layered Poise Long Sleeve Crepe Bolero in Ivory

$24.90

(1)

Poised and polished, this crepe long sleeve bolero elevates casual to dressy outfits effortlessly! Fit & FeaturesCrepe fabric, Fitted long sleeves, Collared neckline, Open front design, Fitted crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Layered Poise Long Sleeve Crepe Bolero in Ivory | Size: XL

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Ready For It Moto Faux Leather Bomber Jacket in Black

$45 $64.90
31% off

(1)

You'll be ready for a chic night out in this sleek moto faux leather bomber jacket! Designed with smooth faux leather fabric, it features a trendy contrast color block pattern for added flair. The jacket is shaped with a standing collar with snap button closures, long sleeves with ribbed hems, a complete zip-front design, side pockets, and a mid-length ribbed hem, offering a relaxed fit for that effortless cool-girl vibe. Style with hoop earrings and ankle booties. Fit & FeaturesFaux leather fabric, contrast color block pattern, woven lining, Standing collar with snap button closures, Long sleeves with tapered ribbed knit hems, Zip-front, side pockets, Mid-length ribbed knit hem, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ready For It Moto Faux Leather Bomber Jacket in Black | Size: M | Leather/Knit Fabric

Windsor Luxe Layer Beaded Sheer Mesh Bolero in Beige

$34.90

(1)

This airy mesh bolero is the perf luxe layer for your formal 'fits featuring all-over beaded embroidery. The long fitted sleeves are designed with flared hems and slit accents. Fit & FeaturesSheer mesh fabric, high stretch, All-over beaded embroidery, Long fitted sleeves, flared hems, slit accents, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Luxe Layer Beaded Sheer Mesh Bolero in Beige | Size: S | Mesh Fabric/Sheer Mesh Fabric

Whimsical Mood Bow Long Sleeve Mesh Bolero in Black

$19.90

Make your outfit even more charming with this sheer mesh bolero featuring fitted long sleeves adorned with bows and slit designs, an open front, and an ultra-cropped hem. Complete the look in platform sneakers. Fit & FeaturesStretchy sheer mesh fabric, Fitted long sleeves, bows and slit designs, Open front, Ultra-cropped length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Whimsical Mood Bow Long Sleeve Mesh Bolero in Black | Size: L | Mesh Fabric/Sheer Mesh Fabric

Casual Cool Vibes Hoodie Bomber Jacket in Taupe

$42.90

Layer on the casual cool vibes with this nylon hoodie bomber jacket offering a relaxed fit perf for everyday wear. Fit & FeaturesNylon-blend fabric with woven lining, no stretch, Drawstring hooded neckline, Zip-front design, Long sleeves with cinched hems , Mid-length cinched hem, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casual Cool Vibes Hoodie Bomber Jacket in Taupe | Size: L | Nylon

Bring The Attitude Lace-Up Bomber Jacket in Brown

$59.90

Vintage vibes, side lace-ups, and a trendy silhouette. This jacket is perfect for layering over a slip dress or denim with attitude! Fit & FeaturesVintage-inspired faux leather fabric, sewn-in woven lining, Long sleeves, snap-button cuffs, Collar neckline, Front zip-up closure, Two front pockets, Side lace-up plackets, Mid-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bring The Attitude Lace-Up Bomber Jacket in Brown | Size: M | Leather

Evening Wear Boleros

When the night calls for a little extra drama, nothing says “I’ve arrived” quite like slipping into a chic evening wear bolero. Think of it as the finishing move to your statement look—one part practical, all parts fabulous. Whether you’re heading to a rooftop party, a bestie’s wedding, or that swanky dinner you’ve been manifesting, a bolero is your secret weapon for instant polish. It’s the kind of piece that lets you play with textures, add a pop of sparkle, or soften a daring neckline in the most effortless way. Picture this: you’re twirling under city lights, your dress catching every glimmer, and your windsor bolero draping just so, making you feel like the main character (because, duh, you are). For anyone who’s ever shivered through a photo op or wished for a little confidence boost before making an entrance, trust—this is your answer. And if you’re searching for a gift that actually gets worn (and doesn’t end up in the “maybe someday” pile), an evening dress bolero is pure gold. It’s one-size-fits-most magic for your glam squad, your mom, your sister, or that friend who always borrows your best stuff.

Choosing the right bolero is like picking your vibe for the night. Want to go full glam? Reach for luxe fabrics like satin, velvet, or sequins that catch every flash and filter. Craving a softer, romantic edge? Sheer mesh, delicate lace, or shimmery tulle can give you that “floaty goddess” moment without hiding your killer dress. And for those moments when you need just a hint of coverage—hello, spaghetti straps and open-back gowns—a cropped bolero is your BFF, offering just enough warmth for breezy evenings without cramping your style. The beauty is in the versatility: layer it over a curve-hugging midi for a sultry vibe, or pair it with a flowy maxi for full-on fairy tale energy. Even better, a bolero is a dream for mixing things up when you want to re-wear your favorite dress but make it look brand new. If you’re the type who loves to be prepared (or just loves a good photo op), stash one in your bag and be ready to transform your look at a moment’s notice. And let’s be real—if you’re planning to dance until your heels come off, a bolero is the move that keeps you cozy without slowing you down.

The Windsor girl knows that every detail counts, and a bolero is the ultimate little luxury that turns an outfit into an entrance. It’s the kind of piece you’ll reach for again and again, whether you’re dressing up for an epic night out or just want to elevate your go-to LBD. And if you’re all about options (aren’t we all?), don’t forget to check out the full lineup of Evening Jackets for even more ways to layer up and stand out. With a windsor bolero in your lineup, you’re ready for whatever the night throws your way—late-night plans, impromptu selfies, or that unexpected after-party invite. No matter how you style it, you’ll be serving looks, turning heads, and making memories that last way past midnight.

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