Vintage Jackets

Vintage jackets are the shortcut to instant cool, no time machine required. Whether you’re channeling retro rebellion or just want to add a little throwback flair to your everyday look, these pieces know how to make an entrance. Think effortless layering, unexpected textures, and that perfectly imperfect vibe only vintage-inspired style can deliver. With vintage jackets in your rotation, every outfit tells a story—and it’s always worth a double take.

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Vintage Vibes Trucker Denim Jacket in Med Denim

$46.90

A cropped, acid wash cotton denim jacket in medium blue with relaxed sleeves and classic button details.

Cropped Attitude Faux Leather Jacket in Black

$49.90

A black faux leather jacket with a cropped hem, front zip closure, and classic collar neckline.

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Trailblazer Faux Suede Fringe Jacket in Brown

$26.97 $59.90 55% off

A cropped brown faux suede jacket featuring dramatic fringe trim and a classic collared neckline.

Wild Side Faux Fur Shawl in Leopard

$28.90

A plush leopard-print faux fur shawl with a satin lining for bold, glamorous layering.

Ultra Game NBA Celtics Satin Bomber Jacket in Green

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Ultra Game NBA Celtics Satin Bomber Jacket in Green

$53.94 $89.90 40% off

A green satin bomber jacket featuring quilted stitching, bold Celtics logos, and striped ribbed trim.

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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 Red

$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 Red | Size: XL | 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: XL

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

Windsor 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: S | 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

Vintage Jackets

There’s something undeniably magnetic about a vintage jacket—the kind that feels like it’s lived a few lives before it ever found its way into your closet. Maybe it’s the perfectly worn-in denim, the soft patina of faux leather, or the playful nostalgia stitched into every detail. Vintage-inspired jackets don’t just keep you warm; they tell a story, adding instant personality to whatever you’re wearing (even if that’s just your favorite old jeans and a tee on a drizzly February afternoon). These are the pieces that transform a basic outfit into a conversation starter, that make you feel like you’ve borrowed something special from your effortlessly cool aunt or scored a hidden gem at a flea market. And let’s be real—there’s nothing quite like the confidence boost you get from tossing on a jacket that looks like it’s straight out of a retro film reel. Whether you’re layering up for a brisk walk to your favorite coffee spot, heading out for a late-night drive, or just looking for an easy way to add a little edge to your everyday, vintage jackets are your go-to for making the ordinary feel extraordinary.

Shopping for vintage-inspired outerwear is all about finding the right balance between timeless appeal and modern comfort. Think about what you want from your jacket: Are you after that oversized, slouchy silhouette that feels borrowed from the ‘90s, or do you gravitate toward cropped cuts with a hint of ‘70s glam? Pay attention to the details—contrast stitching, bold hardware, and unexpected linings can all elevate your look without feeling costume-y. And don’t underestimate the power of versatility. A great vintage jacket works just as well thrown over a slip dress for date night as it does paired with joggers and sneakers for a weekend brunch. These pieces make incredible gifts, too, especially for the friend who’s always raiding thrift stores or the sibling who loves to mix old-school vibes with new trends. There’s a sense of thoughtfulness in gifting something that feels both personal and practical, especially when it comes from a collection like vintage clothing Windsor, where every jacket is curated to deliver standout style without the sticker shock.

February’s unpredictable weather makes this the perfect moment to lean into layers that look as good as they feel. A vintage jacket isn’t just a buffer against the cold—it’s a style statement that adapts to your mood, your plans, and your ever-evolving aesthetic. Slip one on to add a little attitude to a floral skirt, or let it toughen up your favorite loungewear set for those days when you’re running errands but still want to turn heads. The best part? These jackets aren’t precious; they’re made to be lived in, loved, and styled your way, season after season. If you’re ready to explore more ways to top off your look with that effortlessly cool vibe, check out the full edit of Cool Jackets and discover your next forever piece.

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