Dressy Vests

Ready to elevate your wardrobe game with a piece that's as versatile as it is chic? Dive into our collection of dressy vests, where style meets sophistication in the most fabulous way. Whether you're layering up for a night out or adding a polished touch to your office ensemble, these vests are your go-to for turning any outfit from simple to standout. With endless styling possibilities, you'll be serving looks that are anything but basic. So go on, channel your inner fashionista and let these dressy vests do the talking!

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Glow Up Button-Front Cropped Vest in Gold

Sale

Windsor Glow Up Button-Front Cropped Vest in Gold

$6.97 $26.90 74% off

A gold lurex knit vest featuring a sleeveless V-neckline and a single button-front closure.

Windsor Party Glow Glitter Mesh Bolero in Black

$19.90

A shimmering black glitter mesh bolero with long fitted sleeves and a cropped hem.

Fashionable Edge Button Down Faux Leather Vest in Black

Sale

Fashionable Edge Button Down Faux Leather Vest in Black

$9.97 $44.90 78% off

A sleek black faux leather vest with button-down front and square neckline for edgy style.

Now Trending

Sheer Mesh Flared Sleeve Bolero in White

$16.90

(28)

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

Windsor Exclusive Chic Removable Faux Fur Long Sleeve Bolero in Black

$39.90

(22)

This bolero is the perfect piece for a chic, exclusive look! Designed on smooth ribbed knit fabric, it's a style you'll obsess over, featuring a removable plush faux fur neckline, fitted long sleeves with removable faux fur cuffs, an open front design, and an ultra-cropped hem. Fit & FeaturesSmooth rib knit fabric, moderate stretch, Plush faux fur neckline, faux fur is removable, Fitted long sleeves, removable plush faux fur cuffs, Open front design, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Exclusive Chic Removable Faux Fur Long Sleeve Bolero in Black | Size: L | Knit Fabric

Windsor Sheer Mesh Blouson Sleeve Bolero in Black

$19.90

(17)

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: M | Mesh Fabric/Sheer Mesh Fabric

Luxe Affair Removable Faux Fur Bolero in Burgundy

$39.90

(12)

When the vibe calls for drama, this is the bolero. Soft rib knit meets removable faux fur trim for a look that’s pure Old Hollywood with a modern luxe. Whether it’s a cocktail party or a fancy soirée, this bolero guarantees every entrance feels cinematic. Fit & FeaturesSoft rib knit fabric with stretch, Removable faux fur collar, Fitted long sleeves, removable faux fur cuffs, Form-hugging fit, Ultra-cropped length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Luxe Affair Removable Faux Fur Bolero in Burgundy | Size: S | Knit Fabric

Windsor Abundant Luxury Faux Pearl Bead Bolero in White

$34.90

(9)

Perfect for any special occasion, this mesh bolero is the epitome of luxury! This sheer mesh bolero is designed with fitted long sleeves with flared slit cuffs, an open front design, and an ultra-cropped hem for a delicate yet modern touch. Adorned with faux pearl and beaded embellishments, this bolero shrug exudes sophistication and elegance. Complete the look in dressy block heels. Fit & FeaturesFaux pearl and beaded embellishments, Sheer mesh fabric, Open front design, Ultra-cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Abundant Luxury Faux Pearl Bead Bolero in White | Size: S | Mesh Fabric/Sheer Mesh Fabric

Party Glow Glitter Mesh Bolero in Black

$19.90

(5)

Glow at the party in this shimmering glitter mesh bolero to layer over your formal dress! It features long fitted sleeves, an open-front design, and cropped hem. Fit & FeaturesLong fitted sleeves, Open-front design, Cropped hem, Glitter mesh sheer fabric , Moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Party Glow Glitter Mesh Bolero in Black | Size: M | Mesh Fabric

Chic And Sheer Mesh Ruched Sleeve Bolero in Black

$16.90

(4)

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

Autumn Luxe Faux Suede Trench Jacket in Brown

$59.90

(4)

Your fall staple, sorted. This faux suede trench jacket nails cozy-chic with its belted waist and tailored finish—perfect for crisp days, strolling downtown, and everything in between! Fit & FeaturesSmooth faux suede fabric, Long sleeves with button cuffs, Collared neckline, front pockets, Button-down front closures, Belted tie-waist, Tailored short-length silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Autumn Luxe Faux Suede Trench Jacket in Brown | Size: L

Couch Club Chenille Bolero in Brown

$29.90

(2)

For the girls who lounge like it’s an art form. This chenille bolero serves soft luxury with its fuzzy texture and chill-but-chic vibe. Style with the matching catsuit to officially master cozy glam. Shop Matching Catsuit: Couch Club Chenille CatsuitFit & FeaturesSoft ribbed chenille fabric, moderate stretch, Long sleeves, Ultra-cropped hem, Relaxed fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Couch Club Chenille Bolero in Brown | Size: XS

Off Duty Cool Faux Leather Zip Up Bomber in Black

$49.90

(1)

The layer you throw on when the outfit already hits—but needs attitude. This faux leather bomber brings that effortless, pulled-together edge that works day to night without overthinking it. Fit & FeaturesSmooth faux leather fabric, Classic bomber silhouette with relaxed structure, Collared neckline for a clean finish, Long sleeves with elasticized cuffs, Front pockets, Front zipper closure with elasticized hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Off Duty Cool Faux Leather Zip Up Bomber in Black | Size: L

Dressy Vests

Dressy vests are having a major moment, and honestly, it’s about time. There’s something undeniably chic about slipping into a tailored vest—whether you’re layering it over a crisp blouse for a boardroom-ready look or styling it solo with high-waisted trousers for a night out that starts with dinner and ends with dancing. The power of a dressy vest lies in its versatility: it’s the ultimate style chameleon, ready to elevate your everyday denim or add a polished edge to a flowy midi skirt. In the heart of winter, a windsor vest is your secret weapon for layering—think of it as the piece that pulls your whole look together without adding bulk. A structured silhouette instantly sharpens up cozy knits, while a softer, draped vest brings a little movement and sophistication to even your most lived-in basics. And when the invite says “festive but not formal,” nothing threads that needle quite like an elegant vest. It’s the ideal solution for those “what do I wear?” moments, when you want to look put-together but not overdone.

If you’re shopping for yourself or searching for a gift that feels both thoughtful and trend-forward, dressy vests are an inspired pick. They work for just about anyone—your best friend who’s always mixing textures, your sister who’s building her first work wardrobe, or that cousin who lives for a good statement layer. What makes them such a crowd-pleaser is their ability to transition seamlessly from day to night, office to after-party, or brunch to gallery opening. Picture this: a fitted vest over a turtleneck for a sleek, city-cool vibe, or a satin vest paired with wide-leg pants for a touch of retro glam. Even if your style leans minimalist, a well-chosen vest adds just enough interest to make your outfit feel intentional—without ever trying too hard. And for those who love to experiment, a dressy vest is basically a blank canvas: belt it, layer it, button it up, or leave it open. There’s no wrong way to wear one, and that’s the beauty of it. When gifting, it’s a safe bet for anyone who appreciates pieces that work overtime—especially during January, when layering is both a necessity and a style opportunity.

When it comes to choosing the right vest, pay attention to fabric, fit, and finish. A tailored fit flatters just about every body type, while details like gold buttons, subtle embroidery, or a satin lapel can take a vest from simple to standout. If you’re after a piece that will outlast trends, stick to classic colors like black, ivory, or charcoal—these shades play well with everything and feel fresh year-round. For those who like a little drama, don’t shy away from bold hues or unexpected textures; a velvet or faux leather dressy vest can turn even the most basic jeans-and-tee combo into a full look. And if you’re in the mood to see what’s trending, or just want to browse the latest cuts and colors, check out the lineup on our Modern Vests page for inspiration. Whether you’re building a capsule wardrobe or looking for that one piece to refresh your rotation, a dressy vest is the kind of investment you’ll reach for again and again—proof that sometimes, the simplest updates make the biggest impact.

Reset Your Password

Email Sent

Order Status

Dressy Vests

Home Dressy Vests

Now Trending

Dressy Vests

Related Collections