Cool Weather Outfits
Cool weather outfits are your ticket to slaying every chilly-day vibe without missing a beat. Whether you’re making power moves at brunch, planning a rooftop hang with your ride-or-die crew, or just living your main character moment, these looks have your back. Get ready to layer up, turn heads, and keep the good vibes rolling—because cold days are no match for your hot style.
$52.90
A trendy olive twill crop jacket with a fleece-lined hoodie, perfect for cozy, casual nights.
$49.90
A sleek black faux leather jacket with a collared neckline and zip-up front closure.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$39.90
A chic pair of black high-rise skinny pants in coated faux leather with minimal stretch.
$49.90
A black faux leather cropped jacket with an asymmetrical zipper and adjustable waist belt for edgy style.
$29.90
A natural oversized knit sweater bolero with slouchy sleeves and an ultra-cropped hem.
$49.90
A stylish pair of black high-rise cargo denim jeans with a straight-leg silhouette and flap pockets.
$39.90
An ivory knit bolero with faux fur cuffs and collar, featuring an ultra-cropped hem and open front.
$39.90
A sleek pair of black faux leather pants with a high-rise waist and straight-leg silhouette.
$49.90
A brown faux leather biker jacket with zipper details and a cropped hem for an edgy look.
$46.90
An acid-wash black denim jacket with a standing collar and cropped hem for an edgy look.
$24.90
A chic ivory crepe bolero with fitted long sleeves and an open front design.
$44.90
A sleek black faux leather cropped blazer with a relaxed fit and lapel collar.
$45 $64.90 31% off
A sleek black faux leather bomber jacket with a trendy color block pattern and relaxed fit.
$32.90
A brown cotton knit bolero sweater featuring relaxed long sleeves and an ultra-cropped open front design.
$42.90
A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual wear.
$54.90
A burgundy faux leather moto jacket featuring a belted crop hem and zippered pockets.
$49.90
A chic ivory faux leather jacket with striped sleeves, studded collar, and zippered pockets.
$59.90
A charcoal faux leather bomber jacket with a cropped oversized fit and zipper front closure.
$44.90
A trendy denim moto jacket featuring a cool faded design and fitted cropped hem.
$49.90
A brown faux suede moto jacket with an asymmetric zip-front and belted waist for edgy style.
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Step out in style in this mesh panel crop jacket— the perfect layering piece to elevate any look. This unique illusion stripes sheer panel design definitely creates an eye-catching look and layers seamlessly with bodycon dresses or chic mini-skirt outfits. The lightweight fabric is a quick and easy piece to drape over your shoulders for a dramatic look or worn on top of a sleek jumpsuit ensemble for date night or a stylish happy hour soiree. Fit & FeaturesCrew neckline, Long sleeves, Illusion stripes, Cropped hem, Faux leather and mesh fabric, Form-hugging fit, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Faux Leather Illusion Striped Jacket in Black | Size: S | Leather/Mesh Fabric/Mesh Fabric
Look edgy for the ride in this faux leather biker jacket whether you're a passenger or behind the wheel! Featuring a mock neckline with snap-button closure, long sleeves with zipper cuffs, a front zipper closure, faux zipper pockets, and a cropped hem with a snap-button strap, this cool faux leather jacket is the perfect way to take your style to the next level. Complete the look with knee-high boots. Fit & FeaturesLong sleeves, zipper cuffs, Mock neckline, snap-button closure, Front zipper closure, faux zipper pockets, Cropped hem, snap-button closure strap, Faux leather fabric, sewn-in woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Along For The Ride Faux Leather Biker Jacket in Black | Size: XL
Fit & FeaturesFaux leather fabrication, sewn-in woven lining, Collared lapel neckline, Storm flap accent, Double-breasted button closure, Long sleeves, Adjustable belted waist, Side pockets, Long hem length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic Muse Faux Leather Belted Trench Coat in Brown | Size: L
Layer on a chic vibe with this sleek faux leather cropped blazer. The cropped relaxed silhouette will give your 'fit that effortlessly cool look. Fit & FeaturesSmooth faux leather fabric with sleek woven lining, no stretch, Lapel collar, Long sleeves, Cropped hem, Relaxed fit, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Chic Layer Faux Leather Cropped Blazer in Black | Size: M
Serve modern iconic vibes in this oversized faux leather moto jacket with trendy belted and buckle accents and a cropped hem that flaunts your figure. Pair with jeans. Fit & FeaturesFaux leather fabric with woven lining, no stretch, Collared neckline with lapels, Zippered lined front pockets, Long sleeves, Belted accent with buckle and metal grommets, Cropped hem , Oversized fit, Free Shipping on All Orders Over $75. | Windsor Modern Icon Oversized Faux Leather Belted Moto Jacket in Ivory | Size: M
You'll be here to slay your next night out in this sleek faux leather vest. The tie-front design and fitted cropped silhouette create that snatched look. Fit & FeaturesFaux leather fabric with knit lining, minimal stretch, Sleeveless V-neckline, Tie-front design, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here To Slay Faux Leather Cropped Vest in Black | Size: M | Leather/Knit Fabric
A stylish faux suede moto jacket with fringe detailing that causes a scene at concerts, festivals, and trips to the West! Fit & FeaturesFaux suede fabric, Long sleeves, Lapel collar neckline, Fringe detailing, Moto style, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stylish Out West Faux Suede Fringe Moto Jacket in Brown | Size: L
Keep your fall and winter wardrobe trendy with this sleek faux leather blazer! It features a lapel collar, an open front with a single button closure, long sleeves, front pockets, and a chic oversized fit. The faux leather fabric includes a smooth lining. Style over a corset top and mini skirt. Fit & FeaturesLapel collar, Open front, single button closure, Long sleeves, Dual front pockets, Slit accent at the back, Faux leather fabric, smooth lining, no stretch, Oversized fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Keep It Trendy Oversized Faux Leather Blazer in Brown | Size: L
Fashionable-edge combine on this faux leather vest to upgrade your concert or festival fits'! Fit & FeaturesSleek faux leather fabric, Square neckline, Wide shoulder straps, Button down front closures, Front pockets, Split center front hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fashionable Edge Button Down Faux Leather Vest in Black | Size: S
Hop on the style train with the cool girl chic striped faux leather jacket. Rock those stripes and studded collar, zip up, and flaunt the fitted cropped hem. It's your new go-to vibe! Fit & FeaturesFaux leather fabric with smooth woven lining, no stretch, Striped design down the shoulders and sleeves, Standing collar neckline with studded detailing and button closure, Zip-front, Dual zippered lined pockets, back buckle and button strap detailing, Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cool Girl Chic Striped Faux Leather Jacket in Ivory | Size: L
Cool Weather Outfits
When cool weather rolls in and the air gets a little crisp, it’s time to break out the layers and embrace the art of cozy style. Whether you’re dashing out for a coffee run, heading to class, or planning a late-night adventure with your crew, cool weather outfits are all about keeping you warm without sacrificing your vibe. Think of it as your personal toolkit for turning chilly days into your runway—where every layer is a power move and every accessory is a statement. The real secret? It’s all in the mix: start with a base layer that hugs your skin and wicks away moisture (hello, soft thermals and buttery knits), then stack on insulating pieces like chunky sweaters or plush fleece pullovers. Top it off with an outer layer that can handle whatever the day throws at you—puffer jackets, tailored wool coats, or even a windbreaker if you’re feeling sporty. Don’t forget the finishing touches: a beanie that covers your ears, a scarf that doubles as a blanket, and gloves that keep your hands toasty while you text your bestie. And let’s be real, waterproof boots with killer tread are a non-negotiable for those surprise puddles and slick sidewalks.
Cool weather outfits aren’t just about braving the chill—they’re about making every moment count, whether you’re gifting a snuggly sweater to your BFF, surprising your sis with a new coat, or treating yourself to that statement piece you’ve been eyeing. These pieces make unforgettable gifts because they wrap your favorite people in warmth and style, showing them you’ve got their back when the temperature drops. And for the girl who’s always on the go, adjustable layers are a game-changer—think zip-up fleeces and vests you can peel off when the sun peeks out or pile on when the wind picks up. The real magic happens when you play with textures and colors: go bold with cable knits, soft with cashmere blends, or edgy with faux leather and sherpa trims. It’s all about crafting a look that’s uniquely you, ready for spontaneous Insta shoots, late-night bonfires, or that last-minute invite to a rooftop hang. And if you’re gearing up for something a little extra—like a fancy dinner or a glam night out—don’t miss our curated picks for Winter Event Outfits to keep your style game strong no matter where the night takes you.
Expert tip: When you’re building your cool weather lineup, pay attention to the details that make a difference—think moisture-wicking fabrics for your base layers to keep you dry, looser fits for airflow and comfort, and outerwear that balances insulation with breathability. Merino wool, fleece, and lightweight down are your MVPs for warmth without the bulk, while waterproof materials and faux fur-lined hoods bring the drama and the function. Accessories like hats, gloves, and scarves aren’t just practical—they’re your chance to play with pops of color, bold prints, and textures that turn heads. And trust, nothing feels better than stepping out into the cold knowing you’re wrapped in a look that’s equal parts comfort and confidence. So go ahead, layer up and own every chilly day like it’s your personal runway—because with the right outfit, you’re unstoppable.