Autumn Workwear

Autumn workwear just got a major upgrade, babe. Whether you’re running the boardroom or running to grab coffee, these looks are here to make your nine-to-five anything but basic. From power moves to after-hours plans, we’re serving up styles that keep your confidence high and your vibe unstoppable. Who says office chic can’t be fun? With autumn workwear this cute, you’ll have everyone wondering how you make it look so effortless.

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Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black

$34.90

A chic black crepe trouser with a high-rise waist and straight-leg silhouette for workwear elegance.

Walking The Walk Faux Leather Straight Leg Pants in Black

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Walking The Walk Faux Leather Straight Leg Pants in Black

$39.90

A sleek pair of black faux leather pants with a high-rise waist and straight-leg silhouette.

Windsor Out For The Day High-Rise Cargo Pants in Brown

$42.90

A stylish pair of brown high-rise cargo pants with adjustable drawcord hem and multiple pockets.

Windsor Zip It and Chill Mid-Rise Cargo Pants in Brown

$46.90

A pair of brown woven cargo pants featuring zippered pockets, a mid-rise waist, and adjustable cuffs.

Windsor Keep It Trendy Oversized Faux Leather Blazer in Brown

$54.90

A chic brown oversized faux leather blazer with a lapel collar and smooth lining.

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High-Rise Coated Skinny Pants in Black

$39.90

(118)

Elevate your wardrobe with these essential pair of faux leather pants! These chic coated skinny pants feature a high-waist fit, waistband with belt loops, two back pockets, and hidden zipper closure. Style these high-rise pants with a sleek mesh bodysuit, corset top, or blouse for a chic and fierce look. Fit & FeaturesHigh-rise waist, belt loops, Front button and hidden zipper closure, Faux front pockets, two back pockets, Skinny leg design, Coated faux leather fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor High-Rise Coated Skinny Pants in Black | Size: S | Leather

Forever On Trend High Rise Ponte Capri Pants in Brown

$28.90

(27)

Slip into these classic and chic ponte capri pants for effortless style! Channel a 90s vibe in these pants featuring a flattering high-rise waist, form-hugging fit, and flirty side slit accents along the hem. Complete the look in a basic tee and sandals! Fit & FeaturesPonte knit fabric, minimal stretch, High-rise waist, Form-hugging fit, Side slit accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Forever On Trend High Rise Ponte Capri Pants in Brown | Size: M | Knit Fabric

Walking The Walk Faux Leather Straight Leg Pants in Black

$39.90

(24)

In these faux leather pants, you'll be walking the walk of cool-effortless style! They feature a flattering high-rise waist and straight-leg silhouette on coated faux leather fabric that offers a sleek look for workwear or everyday 'fits. Complete the look in a smooth bodysuit and block heels. Fit & FeaturesHigh-rise waist, Straight-leg silhouette, Front button and hidden zipper closure, Faux front pockets, functional back pockets, Coated faux leather fabric, slight stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Walking The Walk Faux Leather Straight Leg Pants in Black | Size: M

Windsor Classic And Chic Wide-Leg Trouser Pants in Black

$35.90

(20)

These classic and chic ponte knit trouser pants feature a high-rise elasticized waist with a hip-hugging fit and a wide-leg hem. The vertical seam running down the front of each leg will create a flattering silhouette you'll love. Fit & FeaturesPonte knit fabric with moderate stretch, High-rise elasticized waist, Vertical front seams, Hip-hugging fit, Wide-leg silhouette, Pants in size small have an 11" front rise with a 31" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classic And Chic Wide-Leg Trouser Pants in Black | Size: XS | Knit Fabric

Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black

$34.90

(13)

Look stylish and posh for your nine-to-five in these crepe trouser pants! Designed with a flattering high-rise waist and front pin-tuck detailing going down the straight-leg silhouette, you'll feel so confident to take on the day. Complete the look in an oversized blazer and heels. Fit & FeaturesCrepe fabric with stretch, High-rise waist, Pull-on-and-off styling, Straight-leg silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Nine To Five Straight-Leg Crepe Trouser Pants in Black | Size: L

Sleek Polish High-Rise Flare Trouser Pants in Black

$42.90

(9)

Sleek, sculpted, and made to move with you. These high-waist flare pants blend polished tailoring with a flattering seam detail—perfect for dressing up your 9-to-5 or elevating your weekend look. Fit & FeaturesSmooth woven fabric, High-rise waist, belt loop accents, Hidden front zipper and hook-eye fasteners, Hip-hugging fit, Seam detailing down the front, Flare hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Polish High-Rise Flare Trouser Pants in Black | Size: S | Woven Fabric

Sleek Business High-Rise Faux Leather Flare Pants in Black

$39.90

(7)

These faux leather pants feature a flattering high-rise waist, hip-hugging fit, and a trendy flare hem on coated fabric for a sleek look. Perfect for styling with a graphic tee and booties. Fit & FeaturesCoated faux leather fabric, slight stretch, High-rise waist, Hip-hugging fit, flare hem, Front button and hidden zipper closure, Two-pocket styling, Pants have an 11" front rise with a 30.5" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Business High-Rise Faux Leather Flare Pants in Black | Size: XS

Windsor Chic And Confident Pinstripe Flared Trouser Pants in Black

$46.90

(4)

Sharp lines, chic confidence. These pinstripe trouser pants hug through the hips, flare out at the hem, and instantly pull an outfit together whether you’re dressing them up or keeping it low-key. Style with the matching vest top! Shop Matching Vest: Chic And Confident Pinstripe VestFit & FeaturesPinstripe print, Knit fabric, Low-rise waistband with belt loops, Slim fit through hip and thigh, Flared leg silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic And Confident Pinstripe Flared Trouser Pants in Black | Size: L

Windsor Trendsetter Alert Coated Faux Leather Flared Pants in Brown

$39.90

(3)

Set the trends in this coated faux leather flare pant featuring a sleek high-rise waist and a flattering straight-leg fit that flares out at the hem. Pair with a long sleeve top. Fit & FeaturesCoated faux leather fabrication, High-rise waist, Single button with hidden zipper closure, Straight-leg fit, Flared hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendsetter Alert Coated Faux Leather Flared Pants in Brown | Size: XS

Windsor Low Effort Tie Waist Flare Pants in Black

$34.90

(3)

Low effort, high payoff—these pants do all the talking. The sleek flare pants shape with a soft tie detail create an easy, flattering fit that works for nights out, dinner plans, or styled up with a bandeau. Fit & FeaturesKnit stretch fabric, Low-rise tie waist design, Hip-hugging fit, Flared hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Low Effort Tie Waist Flare Pants in Black | Size: XS

Autumn Workwear

Autumn workwear is all about that perfect blend of polish and comfort—think layers you can actually move in, textures that look luxe but feel effortless, and colors that make you want to step outside even when the mornings start crisp. This is the season when your closet gets a little more interesting: lightweight knits, tailored trousers, midi skirts, and blazers that mean business (but never feel stuffy). Whether you’re heading back to the office after a summer of remote work, logging into Zoom calls from your kitchen, or just looking to upgrade your daily uniform for those in-person coffee runs, autumn workwear is designed to keep up with your plans—and your mood swings. You want pieces that multitask as hard as you do, going from early meetings to late dinners, or from the boardroom to brunch without missing a beat. It’s not just about looking put-together; it’s about feeling ready for anything, even if that “anything” is just a surprise rain shower or an impromptu happy hour.

Shopping for autumn workwear is its own kind of ritual. Maybe you’re refreshing your wardrobe after months of heatwaves and sundresses, or maybe you’re building out a capsule collection that actually works for your real life (yes, you can absolutely wear that midi dress with sneakers and a trench coat). Consider fabrics that transition well—think ponte, tweed, or soft ribbed knits that hold their shape but never feel restrictive. Look for details that elevate without overwhelming: a subtle puff sleeve here, a sleek belt there, or a pop of autumnal color that instantly upgrades your basics. These are the pieces you’ll reach for on repeat, the kind that make getting dressed feel less like a chore and more like a tiny celebration. And if you’re shopping for someone else—maybe a friend who just landed a new job, a sister heading back to campus, or a partner who deserves a little weekday confidence boost—autumn workwear is a thoughtful, practical gift that says “I see you, and I know you’re about to crush it.” Don’t forget the finishing touches: a structured bag, a pair of boots you’ll actually want to walk in, or a scarf that pulls everything together without trying too hard.

As the days get shorter and your calendar fills up, layering becomes your best friend. Start with a foundation of versatile staples—think button-downs, mock necks, or easy-wearing knits—then add outer layers that bring both warmth and personality. A great jacket is non-negotiable this time of year, and nothing says “I’ve got this” like a tailored piece that works with everything from jeans to midi skirts. If you’re looking to upgrade your outerwear game, check out our edit of Stylish Autumn Jackets for options that deliver on both function and flair. The right workwear isn’t just about meeting a dress code—it’s about meeting the moment, whether that means powering through deadlines, catching up with friends after hours, or just feeling like your best self when you step out the door. Autumn is the season for fresh starts and new routines, and your wardrobe should make every day feel a little more intentional, a little more inspired, and a lot more you.

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