Workwear has always had a firm grip on men’s fashion. Alongside sportswear and military gear, it forms one of the foundational pillars of modern menswear. Think about how many wardrobe staples—like jeans, T-shirts, or overshirts—can trace their roots back to workwear.
The workwear look has had its moments over the years. Remember the early 2010s “heritage” craze? Beards, flannel shirts, raw denim, and Red Wing boots were everywhere. While that specific trend has mellowed, vintage-inspired workwear is back in a big way—this time with a focus on mid-century styles, pre-worn finishes, roomy silhouettes, and a heavy dose of Japanese flair.
Instead of spending hours sifting through thrift racks, here are some of the best brands keeping the vintage workwear flame alive.
Cherry Los Angeles
- Mechanic Printed Cotton-Canvas Trucker Jacket
- Logo-Embroidered Checked Cotton-Flannel Shirt
- Wide-Leg Distressed Jeans
- Truck Appliquéd Logo-Embroidered Baseball Cap
Cherry Los Angeles is all about the details. In a sea of fast fashion, this brand stands out with real-deal reworkings of old-school American workwear and sportswear. The designs are bold, the silhouettes are relaxed, and the aesthetic leans hard into classic Americana.
The best part? Everything is made in the USA, so authenticity is guaranteed.
Shop now at MR PORTER
The Real McCoys
- LOT.S003 Denim
- Wabash Chore Coat
- Buco Nylon Rider’s Vest
- 8HU Houndstooth Flannel Shirt
The Real McCoys take obsession to the next level. This Japanese label is known for crafting exacting replicas of mid-century American workwear and military clothing—right down to the fabrics, threads, and construction methods.
Yes, it’s pricey. But if you’re serious about vintage accuracy and craftsmanship, this brand delivers like no other.
Shop now at The Real McCoys
RRL (Double RL)
- Straight-Leg Distressed Jeans
- Logo-Appliquéd Cotton-Corduroy Cap
- Preston Striped Bouclé Overshirt
- Corduroy-Collar Canvas Jacket
Ralph Lauren’s RRL line is a love letter to the American frontier. Inspired by ranch life and rugged utility wear, RRL blends timeless silhouettes with vintage washes and top-notch materials.
It’s more expensive than standard Polo gear, but the craftsmanship justifies the splurge—plus, you’re not likely to see your outfit twin in one of these pieces.
Shop now at MR PORTER
Carhartt
- Rugged Flex™ Duck Relaxed Fit Jacket
- Relaxed Fit Fleece-Lined Shirt Jac
- Loose Straight Duck Dungaree
- Heavyweight Flannel Plaid Shirt
Carhartt is the OG of American workwear, making gear for hardworking folks since 1889. Built for durability, the brand’s classic pieces are now fashion staples—especially through its Carhartt WIP line.
WIP adds a stylish spin to the rugged basics, with street-ready fits, bold logos, and more experimental cuts. It’s workwear that’s gone global.
Shop now at Carhartt
Kapital
- Lumber Embroidered Cargo Trousers
- Cactus Denim Jacket
- Wide-Leg Panelled Drawstring Trousers
- Wool-Blend Tweed Overshirt
Kapital takes American styles—denim, flannel, military pieces—and filters them through a bold Japanese lens. Expect wild patterns, patchwork, fringe, embroidery, and cuts that break the mold.
Originally a denim label, Kapital has become one of Japan’s most creative and influential fashion brands.
Shop now at MR PORTER
Levi’s Vintage Clothing
- 1936 Type I Jacket
- 1953 Type II Jacket
- 1947 501® Jeans
- Lot 201 Jeans
Levi’s has long been the blueprint for American denim. Their Vintage Clothing line is all about recreating iconic pieces from the brand’s deep archives—faithfully rebuilt with period-correct stitching, fits, and washes.
If today’s Levi’s feel a little too modern, this is where you’ll find the heritage goodness.
Shop now at Levi’s
Needles
- H.D. Buggy Wide-Leg Drawstring Jeans
- Piping Cowboy Satin Jacket
- Logo-Embroidered Shirt Jacket
- Papillon Western Leather Belt
Needles, founded by Keizo Shimizu, twists classic workwear into something entirely new. Expect colorful, bold, often eccentric takes on timeless silhouettes.
Needles pieces are like wearable art—perfect if you want to stand out while still paying tribute to old-school American style.
Shop now at SSENSE
Visvim
- Mayfield Velour-Trimmed Bomber Jacket
- Lumber Shirt
- Social Sculpture Raw Slim Jeans
- Wabanaki Folk Boots
Visvim is in a league of its own—where American vintage meets Japanese artistry. You’ll find bombers, jeans, boots, and shirts, all remixed with painstaking attention to detail, top-tier materials, and a unique point of view.
Yes, the prices are eye-watering. But if fashion is your passion, Visvim might just be worth the investment.
Shop now at Farfetch
Wtaps
- Straight-Leg Pleated Cargo Trousers
- Checked Cotton-Flannel Shirt
- Quilted Work Jacket
Founded by Tetsu Nishiyama, Wtaps blends military uniform aesthetics with Japanese streetwear energy. Think tactical-inspired pants, oversized flannels, and rugged outerwear—all cut with purpose and precision.
It’s this blend of function, form, and fit that’s earned Wtaps a cult following.