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.
$44.90
A casual denim shacket with a relaxed fit, button-up front, and convenient pockets.
$52.90
A brown faux suede trench coat with a tie-front belt and long-length hem.
$52.90
A trendy olive twill jacket with a fleece-lined hoodie, perfect for layering on chill nights.
$46.90 - $49.90
A chic olive cargo jogger with high-rise waist, metal ring trims, and elastic cuffed hems.
$32.90
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.
$49.90
A black faux leather and mesh jacket with illusion stripes, perfect for layering stylish outfits.
$29.90
A natural oversized knit bolero with slouchy sleeves and an ultra-cropped hem for cozy layering.
$39.90
An ivory knit bolero with faux fur cuffs and collar, featuring an ultra-cropped hem and open front.
$49.90
A stylish pair of black high-rise cargo denim jeans with a straight-leg silhouette and flap pockets.
$34.90
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 cropped hem, standing collar, and front zipper closure.
$6.97 $32.90 79% off
A taupe cable knit sweater topper with fitted long sleeves and an ultra-cropped hem for layering.
$45 $64.90 31% off
A sleek black faux leather bomber jacket with a trendy color block pattern and relaxed fit.
$39.90
A sophisticated pair of black ponte knit pants featuring a belted waist and tapered straight leg.
$59.90
An oversized black faux leather blazer with a collared neckline and hidden side pockets.
$44.90
A sleek black faux leather cropped blazer with a relaxed fit and lapel collar.
$44.90
A trendy black acid wash denim shacket with a relaxed fit and button-down front.
$59.90
A light denim trucker jacket featuring charming bow embroidery and a relaxed fit.
$42.90
A taupe nylon hoodie bomber jacket with a relaxed fit and drawstring hood for casual wear.
$59.90
A charcoal faux leather bomber jacket with a cropped oversized fit and zipper front closure.
$49.90
A sleek black faux leather jacket with a collared neckline and zip-up front closure.
$24.90
A chic ivory crepe bolero with fitted long sleeves and an open front design.
$39.90
An oversized beige denim bomber jacket with relaxed long sleeves and a zip-up front closure.
$49.90
A chic ivory faux leather jacket with striped sleeves, studded collar, and zippered pockets.
$49.90
A brown faux suede moto jacket with an asymmetric zip-front and belted waist for edgy style.
$54.90
A burgundy faux leather moto jacket featuring a belted crop hem and zippered pockets.
$44.90
A trendy denim moto jacket featuring a cool faded design and fitted cropped hem.
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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: M | Leather/Mesh Fabric/Mesh Fabric
This sleek faux leather trench coat will make every day a stylish elevated affair. It features a collared neckline, long sleeves, a complete snap button-down front, dual chest pockets, dual faux side pockets, a tie-waist belt to create a cinched silhouette, and a short-length hem. Layer this trench over a mini dress styled with tights and thigh-high boots for a chic fall 'fit. Fit & FeaturesCollared neckline, Long sleeves, dual snap buttons, Snap button-down front, Dual chest pockets, dual faux side pockets, Tie-waist belt, short-length hem, Faux leather fabric, no stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Elevated Affair Faux Leather Trench Coat in Black | Size: M
Layer on an elevated and chic style with this faux leather trench. The jacket features a lapel collar, long sleeves, side pockets, a tie-front belt to cinch the waist, and a mid-length, relaxed fit. The smooth faux leather fabric has a moderate stretch. Complete the look with heeled booties. Fit & FeaturesLapel collar, Long sleeves, Side pockets, Tie-front belt, Mid-length, relaxed fit, Lined faux leather fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Elevated And Chic Faux Leather Trench Coat in Black | Size: L
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 Brown | Size: M
Make a stylish impression with this of-the-moment moto jacket. Designed with smooth faux suede fabric, it is shaped with a structured lapel collar with sleek studded accents and long sleeves with studded shoulder straps. The asymmetric zip-front design brings trendy vibes, along with the chic zippered accent and zippered pockets. Pair with the matching mini skirt for an elevated everyday look. Shop Matching Bottoms: Stylish Impression Faux Suede Mini SkirtFit & FeaturesFaux suede fabric, minimal stretch, Lapel collar with studs, Long sleeves with studded shoulder straps, Asymmetric zip-front, Zippered accent, dual zippered pockets, Fitted, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stylish Impression Faux Suede Moto Jacket in Taupe | Size: L
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
Head out the door looking effortlessly sleek in this faux leather oversized blazer for a weeknight dinner or a weekend night out! Fit & FeaturesSleek faux leather fabric, sewn-in woven lining, Relaxed long sleeves, Collared neckline, Hidden side pockets, Runs oversized, 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 Effortlessly Sleek Faux Leather Oversized Blazer in Black | Size: S
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
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: XL
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
Cool Weather Outfits
When the temps start to dip and the air gets that crisp, cozy bite, it’s officially time to level up your look with outfits that bring the heat—without sacrificing your style. Cool weather outfits are all about striking that perfect balance between comfort and confidence, whether you’re heading out for a late-night coffee run, bundling up for a rooftop hang, or just living your best life on the daily. Think layers that move with you, textures that make you want to touch, and silhouettes that flatter every vibe you’re channeling. Shopping for cool weather looks isn’t just about staying warm—it’s about curating a wardrobe that keeps you feeling unstoppable, no matter what the forecast throws your way. From plush knits that hug you in all the right places to statement outerwear that instantly turns the sidewalk into your runway, these pieces are designed to give you that main character energy all season long. And if you’re building a capsule for yourself or picking out a gift for your ride-or-die, these are the styles that promise to deliver those gas-you-up moments with every wear.
There’s something kind of magical about bundling up when the world outside is a little extra chilly. Picture this: you, wrapped in a buttery-soft sweater, hair up in a messy bun, sipping something warm while the city lights twinkle. Or maybe you’re the queen of layering—a sleek turtleneck under a bold jacket, topped off with a scarf that’s basically a wearable hug. These are the pieces you’ll reach for when you want to feel cozy but still look like you could be snapped for a street style roundup. And let’s not forget those spontaneous adventures: impromptu road trips, midnight strolls under the stars, or just kicking back with your crew in a cabin somewhere off the grid. Cool weather outfits are made for those moments, giving you the freedom to say yes to every invite, knowing you’ll look and feel amazing. If you’re shopping for a bestie, these pieces make the ultimate gift—think of them as a love letter in fabric form, perfect for birthdays, holidays, or just because your BFF deserves to be wrapped in style.
No matter what’s on your calendar, having a lineup of cool weather outfits means you’re ready for anything—date nights that turn into sunrise breakfasts, study sessions that end with dance parties, or spontaneous trips to see the first snow. The trick is to mix and match textures, play with color, and never be afraid to let your personality shine through every layer. And if you’re looking to turn up the glam for something extra special, don’t miss our curated picks for Winter Event Outfits—because when the occasion calls for a little drama, you know we’ve got you covered. Dressing for cool weather isn’t just about staying warm; it’s about making every chilly day feel like a reason to celebrate. So go ahead, embrace the layers, own your style, and step out knowing you’re the main event, every single time.