Evening Jackets

Evening jackets are your secret weapon for turning every night out into a main character moment. Whether you’re channeling boss energy or ready to dance ‘til dawn, these styles have your back—literally. Throw one on and watch how the whole vibe shifts: suddenly, you’re unstoppable, untouchable, and totally unforgettable. Your outfit’s about to get the glow-up it deserves—because with evening jackets, you never just show up… you make an entrance.

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On My Way Trucker Crop Denim Jacket

$42.90

A stylish denim jacket with a trucker silhouette, elasticized crop hem, and button-up front.

Windsor Trendy Arrival Denim Moto Jacket

$44.90

A trendy denim moto jacket featuring a cool faded design and fitted cropped hem.

Biker Chic Crop Jacket in Black

$49.90

A black faux leather cropped jacket with an asymmetrical zipper and adjustable waist belt.

Windsor Along For The Ride Faux Leather Biker Jacket in Black

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Windsor Along For The Ride Faux Leather Biker Jacket in Black

$49.90

A black faux leather biker jacket with zipper details and a cropped hem for an edgy look.

Ride In Style Faux Leather Moto Crop Jacket in Red

Ride In Style Faux Leather Moto Crop Jacket in Red

$69.90

A red faux leather moto jacket with long sleeves, zippered pockets, and a trendy striped pattern.

Windsor Edgy Arrival Moto Acid Wash Denim Jacket in Black

$46.90

An acid-wash black denim jacket with a standing collar and cropped hem for an edgy look.

Shift Into Glam Faux Leather Moto Jacket in Black

$64.90

A black faux leather moto jacket with an asymmetrical zipper and adjustable waist belt.

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Biker Chic Crop Jacket in Black

$49.90

(52)

Change gears in a cropped jacket and add a little biker chic-ness to your look! Create an edgy look in this biker moto jacket that features an asymmetrical zipper front with a lapel collar, snap button accents, and an adjustable waist belt. Fit & FeaturesFaux leather fabric with no stretch, smooth lining, Lapel collar, asymmetrical zippered front, Long sleeves with zippered accents, Zipper and snap button accents, Adjustable waist belt, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Biker Chic Crop Jacket in Black | Size: XL | Leather

Scene Stealer Faux Fur Crop Denim Jacket

$49.90

(11)

Serving vintage glam with a rockstar twist. This faux fur trim denim jacket is oversized, plush, and impossible to ignore—the perfect throw-on for concerts, nights out, or everyday styling. Fit & FeaturesDenim fabric, sewn-in knit lining, Faux fur trim collared neckline, Long sleeves, faux fur trim cuffs, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Scene Stealer Faux Fur Crop Denim Jacket | Size: M | Knit Fabric

Ride In Style Faux Leather Moto Crop Jacket in Red

$69.90

(8)

Wherever you're headed, arrive in style! This faux leather moto jacket features long sleeves, a mock neckline with snap-button closure, front zipper closure, zippered pockets for keeping your hands warm, a cropped hem, and a trendy contrast striped pattern for added flair. Complete the look in a tee and slit midi skirt for a cute-edgy vibe! Fit & FeaturesLong sleeves, Mock neckline with snap-button closure, Front zipper closure, zippered pockets, Cropped hem, Contrast striped pattern, Faux leather fabric, sewn-in woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ride In Style Faux Leather Moto Crop Jacket in Red | Size: M

Frost Mode Faux Fur Crop Jacket in Fuchsia

$59.90

(7)

Plush, polished, and made to flex. This zip-up faux fur crop jacket brings cozy luxury to your cold-weather lineup—soft to the touch, cropped to perfection, and ready to elevate every winter fit. Fit & FeaturesPlush faux fur fabric, sewn-in woven lining, Collar neckline, Front zip-up closure, Long sleeves, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Frost Mode Faux Fur Crop Jacket in Fuchsia | Size: S

Street Cue Crop Denim Bomber Jacket in Brown

$54.90

(4)

Off-duty but still on. This cropped denim bomber jacket adds instant cool style to anything you throw it over—because basics deserve better. Fit & FeaturesCotton denim fabric, no stretch, Standing collar neckline, Front hidden zip-up closure, snap-button closures, Front flap pockets, Elasticized cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Street Cue Crop Denim Bomber Jacket in Brown | Size: XL | Cotton

Life In The Fast Lane Crop Moto Jacket in Brown

$69.90

(4)

Experience life in the fast lane in this sleek moto jacket with a bold colorblock design and cropped fit. It’s the perfect jacket to layer over any outfit for a day or night out. Fit & FeaturesFaux leather fabric, color block design, sewn-in woven lining, Standing collar neckline with button closure, Long sleeves, Side zippered pockets, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life In The Fast Lane Crop Moto Jacket in Brown | Size: M | Leather

On My Way Trucker Crop Denim Jacket

$42.90

(3)

Layer on this trucker crop denim jacket on your way out looking fresh. This jacket features long sleeves with button cuffs for versatile styling, a collar neckline for a polished look, and convenient flap pockets. The elasticized crop hem and trucker silhouette add modern flair to the classic denim fabric. Complete the look in a trendy denim midi skirt for a cute fit! Fit & FeaturesDenim fabric, no stretch, Button up front closures, Flap faux pockets, Elasticized crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor On My Way Trucker Crop Denim Jacket | Size: M

At Your Leisure Zip-Up Crop Jacket in Chartreuse

$29.90

(1)

A comfy and cute zip-up crop jacket perfect for post-pilates and grabbing coffee! Pair with the matching bottoms. Fit & FeaturesStretchy rib knit fabric, Fitted long sleeves, Mock neckline, Zip-up front closure, Fitted crop hem, Runs true to size, Shop The Matching Pants: At Your Leisure Mid-Rise Flare Pants Free Shipping on All Orders Over $75. | Windsor At Your Leisure Zip-Up Crop Jacket in Chartreuse | Size: S | Knit Fabric

Polished Edge Crop Bouclé Jacket in Black-2

$59.90

(1)

This bouclé lurex crop jacket serves polished-but-playful energy — sparkly woven texture, gold button details, and a flirty crop length that ties the whole “effortlessly chic” vibe together. It’s giving a holiday party, a gallery opening, and any night you want to look expensive without even trying. Shop The Matching Skort: Polished Edge Ruffle Bouclé SkortFit & FeaturesBouclé lurex woven fabrication, sewn-in lining, Collar neckline, Long sleeves, structured shoulders, Decorative button and pocket detailing, Crop-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Polished Edge Crop Bouclé Jacket in Black-2 | Size: M | Woven Fabric

Cropped Attitude Faux Leather Jacket in Black

$49.90

(1)

From coffee runs to late nights, this faux leather jacket nails that effortless cool-girl vibe in the city! Fit & FeaturesFaux leather fabric, sewn-in woven lining, Long sleeves, Collar neckline, Front zip-up closure, Front pockets, Cropped-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cropped Attitude Faux Leather Jacket in Black | Size: S

Evening Jackets

When the sun dips below the horizon and the calendar says “evening plans,” the right jacket is your secret weapon. Evening jackets aren’t just about keeping warm—they’re the final layer that pulls your whole look together, whether you’re headed to a candlelit dinner, a winter wedding, or that RSVP-required event you’ve been planning for weeks. Think of them as the unsung heroes of your closet: the structured blazers that lend instant sophistication, the cropped boleros that add just the right amount of drama to a sweeping gown, or the leather jacket Windsor fans reach for when they want to dial up the edge without sacrificing elegance. January’s chill calls for outerwear that’s both functional and fabulous, and that’s where Windsor jackets step in—giving you options that go far beyond basic. From longline silhouettes that balance out mini hemlines to cape coats that make every entrance feel like a main character moment (without ever saying it out loud), evening jackets are about more than just coverage; they’re about self-expression. You might find yourself reaching for a sleek dinner jacket with silk lapels for a formal gala, or grabbing a lightweight trench to layer over a slip dress for cocktails downtown. Each piece is designed with intention, meant to complement your outfit and your mood, no matter how the night unfolds.

Evening jackets are a thoughtful gift for anyone who loves to dress up or is always on the go—think your best friend who never misses a party, your sister who’s planning her engagement photos, or your mom who appreciates a timeless wardrobe staple she can wear season after season. These pieces are endlessly versatile: a cropped puffer can take a sequin mini from club-ready to street chic, while a classic peacoat or duster adds polish to even the simplest dress. For those who want to play with proportion, a longline blazer or a tailored leather blazer can redefine your silhouette and bring a modern twist to traditional eveningwear. And if you’re after something that feels a little more unexpected, a cropped bomber or a denim jacket can add a playful, sporty vibe to your night-out look. The beauty of Windsor jackets is their ability to flex with your plans—layer them over a formal maxi for a black-tie affair, or pair with a slip skirt and boots for a dinner that turns into dancing. And if you’re in the mood for something classic with a touch of flair, you’ll want to check out our selection of Black Evening Bolero Jackets, perfect for adding a hint of vintage glamour to any ensemble.

The key to finding your perfect evening jacket is knowing how you want to feel when you walk into the room—confident, comfortable, and completely yourself. Look for details that speak to your style: silk lapels for a hint of luxury, sharp tailoring for that borrowed-from-the-boys energy, or a leather jacket Windsor girls love for its iconic, wear-anywhere cool. Don’t be afraid to mix textures and lengths, especially in winter when layering is both practical and stylish. Evening jackets are about celebrating your individuality, whether you gravitate toward understated elegance or love a bold, statement-making piece. With the right jacket, you’re not just finishing your outfit—you’re setting the tone for the whole night.

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