S2640488_IN_NATURAL_Large_2ae1d9d6-4941-4102-be22-e1df22315723.png
Sweaters
Men's Flannels
Flannels
Long Sleeve Brushed Jersey Henley in Olive features a classic henley style and buttons, ideal for year-round wear.
Henleys & Crews
Man wearing a Long Sleeve Unlined Utility Shirt Jacket in White Pepper, styled with sunglasses at the beach.
Shirt Jackets
Stonewash Knit Johnny Collar Polo in Flint model on the beach, showcasing a textured knit design.
Polos
Collection of denim jeans in various shades of blue, showcasing different styles and washes on a dark background.
Denim
FLORA-MenswearEditorialComposition1-e2e0ccf9.png
Outerwear
Short Sleeve Stripe Denim Shirt in Serenity Blue modeled by a man on the beach, styled with relaxed jeans.
Button Downs
Casual sweatpants in various earth tones: olive, beige, and cream laid out on a textured surface.
Pants
8-inch-twill-shorts-sea-spray-textured-cotton-comfort-fit-men-beachwear.jpg
Shorts
82 products
Model wearing a Long Sleeve Brushed Flannel in Dusk Blue on a dock by the water.
Man wearing Long Sleeve Brushed Flannel in Dusk Blue, outdoors with a rugged look and relaxed pose.
Model wearing a Long Sleeve Brushed Flannel in Dusk Blue, showcasing its classic style and button-down collar.
Long Sleeve Brushed Flannel in Dusk Blue, seen from the back, showcasing the plaid design and button-down collar.
60% OFF
Quick Buy
Long Sleeve Brushed Flannel in Dusk Blue
5.0
Rated 5.0 out of 5 stars
5.0
$26.00 $65.00
A model wearing a Textured Roll Neck Sweater in Blue Ashes, showcasing its soft blend and modern fit.
Textured Roll Neck Sweater in Blue Ashes worn with jeans, highlighting a modern cold-weather outfit for casual styling.
60% OFF
Quick Buy
Textured Roll Neck Sweater in Blue Ashes
$28.00 $70.00
Long Sleeve Brushed Flannel in Beige featuring a button-down collar and plaid design.
Long Sleeve Brushed Flannel in Beige worn by male model, showcasing a classic fit and rustic style.
Long Sleeve Brushed Flannel in Beige worn by model, showcasing classic cut and soft cotton blend fabric.
Back view of a model wearing a Long Sleeve Brushed Flannel in Beige, showcasing its classic plaid design.
60% OFF
Quick Buy
Long Sleeve Brushed Flannel in Beige
5.0
Rated 5.0 out of 5 stars
5.0
$26.00 $65.00
Short Sleeve End-On-End Plaid In Kentucky Blue worn by a model, showcasing its relaxed fit and stylish design.
Short Sleeve End-On-End Plaid In Kentucky Blue shirt featuring a relaxed fit, short sleeves, and button details.
Short Sleeve End-On-End Plaid In Kentucky Blue, showing relaxed fit and button-down collar, featuring subtle heathered effect.
Short Sleeve End-On-End Plaid In Kentucky Blue shown from the back view highlighting its relaxed fit and short sleeves.
66% OFF
Quick Buy
Short Sleeve End-On-End Plaid In Kentucky Blue
3.0
Rated 3.0 out of 5 stars
3.0
$20.00 $60.00
Model wearing Long Sleeve Faux Linen Plaid Shirt in Natural, standing next to classic Land Rover in sunny outdoor setting.
Man wearing Long Sleeve Faux Linen Plaid Button Down shirt in Natural beside a classic green Land Rover in a sunny outdoor setting.
Long Sleeve faux linen plaid button down shirt in natural, made of 100% cotton, featuring a classic fit and cuffed sleeves.
Long sleeve faux linen plaid button down shirt in natural tone, featuring a button-down collar and chest pocket.
66% OFF
Quick Buy
Long Sleeve "Faux Linen" Plaid Button Down in Natural
$22.00 $65.00
Model wearing a Solid Nylon Jacket In Khaki with hood, banded cuffs, and chest pockets.
Solid Nylon Jacket In Khaki worn by a man at the beach, featuring a hood and functional front pockets.
Man wearing a Solid Nylon Jacket In Khaki on the beach with a relaxed coastal vibe.
Man wearing a Solid Nylon Jacket In Khaki, showing the back view with a hood and banded cuffs.
69% OFF
Quick Buy
Solid Nylon Jacket In Khaki
5.0
Rated 5.0 out of 5 stars
5.0
$24.00 $79.00
Short Sleeve Striped Cotton Button Down Shirt In Monaco Blue worn by a model, featuring a button down collar and chest pocket.
Short Sleeve Striped Cotton Button Down Shirt In Monaco Blue worn by a man with a button down collar and chest pocket.
Short Sleeve Striped Cotton Button Down Shirt In Monaco Blue worn by a model with button down collar and chest pocket.
Short Sleeve Striped Cotton Button Down Shirt In Monaco Blue, back view showcasing the striped design and button down collar.
66% OFF
Quick Buy
Short Sleeve Striped Cotton Button Down Shirt In Monaco Blue
4.0
Rated 4.0 out of 5 stars
4.0
$20.00 $60.00
Man wearing a short sleeve solid linen cotton shirt in bright white, ideal for casual and stylish outfits.
Close-up of a man wearing a bright white short sleeve linen cotton shirt with a button-down collar.
Back view of a man wearing a short sleeve solid linen cotton shirt in bright white.
Bright white solid linen cotton fabric for stylish short sleeve shirts, perfect for layered looks and casual wear.
66% OFF
Quick Buy
Short Sleeve Solid Linen Cotton in Bright White
From $20.00
Graphic Tee In Navy featuring outdoor-inspired graphics and a soft crewneck design, perfect for casual wear.
Graphic Tee In Navy featuring weatherproof vintage graphic design on soft jersey fabric.
Men's Graphic Tee In Navy featuring outdoor graphics and soft jersey fabric for comfort.
64% OFF
Quick Buy
Graphic Tee In Navy
5.0
Rated 5.0 out of 5 stars
5.0
$12.00 $34.00
Graphic Tee In Grey Heather featuring outdoor inspired graphics and soft jersey fabric for comfort.
Graphic Tee In Grey Heather featuring vintage outdoor graphics and a soft crewneck design.
Graphic Tee In Grey Heather featuring outdoor inspired graphics and a vintage surf design.
Graphic Tee In Grey Heather featuring weatherproof vintage surf design with sun and waves.
64% OFF
Quick Buy
Graphic Tee In Grey Heather
$12.00 $34.00
Man in roasted russet teddy sherpa pullover with quarter-zip, showcasing plush fleece and cozy design.
Teddy Sherpa pullover in roasted russet, featuring cozy fleece, quarter-zip, and hand warmer pockets.
Back view of a cozy teddy sherpa pullover in roasted russet, showcasing plush fleece and quarter-zip design.
Men's Teddy Sherpa Pullover in Roasted Russet with quarter zip and cozy sweatshirt feel.
52% OFF
Quick Buy
Teddy Sherpa Pullover In Roasted Russet
$36.00 $75.00
Short Sleeve Solid Terry Button Down Shirt In Naval Academy worn by a model by a pool, showcasing casual summer style.
Short Sleeve Solid Terry Button Down Shirt In Naval Academy worn with matching shorts, showcasing a relaxed summer look.
Short Sleeve Solid Terry Button Down Shirt In Naval Academy modeled by a man, showcasing the soft navy fabric and collar.
Short Sleeve Solid Terry Button Down Shirt In Naval Academy on model, showcasing soft terry fabric and button front design.
66% OFF
Quick Buy
Short Sleeve Solid Terry Button Down Shirt In Naval Academy
5.0
Rated 5.0 out of 5 stars
5.0
$20.00 $60.00
Holiday Antique Flannel in True Navy worn by model, showcasing premium brushed flannel, buttoned collar and stylish design.
Holiday Antique Flannel in True Navy worn by model, showcasing premium brushed flannel fabric and buttoned design.
Holiday Antique Flannel in True Navy modeled by a man with a button-down collar.
Close-up of Holiday Antique Flannel in True Navy fabric showcasing navy and green plaid pattern.
60% OFF
Quick Buy
Holiday Antique Flannel in True Navy
4.9
Rated 4.9 out of 5 stars
4.9
$26.00 $65.00
Short Sleeve Cotton Shirt With Ticking Stripe In Cloud worn by a model, featuring a button down collar and chest pocket.
Short Sleeve Cotton Shirt With Ticking Stripe In Cloud shown from the back, featuring a button down collar and striped pattern.
Short Sleeve Cotton Shirt With Ticking Stripe In Cloud featuring embroidered details and button down collar.
Short Sleeve Cotton Shirt With Ticking Stripe In Cloud worn by a model, featuring a button-down collar and embroidery.
66% OFF
Quick Buy
Short Sleeve Cotton Shirt With Ticking Stripe In Cloud
5.0
Rated 5.0 out of 5 stars
5.0
$20.00 $60.00
Man in stylish jacket and shorts posed by a waterfront, showcasing a relaxed yet fashionable look.
Contemplative man in sporty jacket sitting by water, reflecting on a cloudy day.
69% OFF
Quick Buy
Nylon Zip Up Color Block In Sharkskin
5.0
Rated 5.0 out of 5 stars
5.0
$24.00 $79.00
Solid Terry Drawstring Short In Naval Academy worn by model, showcasing soft fabric and drawstring waist.
Model wearing Solid Terry Drawstring Short In Naval Academy with matching striped shirt, showcasing soft fabric and casual style.
Model wearing Solid Terry Drawstring Short In Naval Academy with matching shirt, showcasing soft, weatherproof fabric.
Solid Terry Drawstring Short In Naval Academy, showing back view of soft navy shorts with pockets.
66% OFF
Quick Buy
Solid Terry Drawstring Short In Naval Academy
$20.00 $60.00
Short Sleeve Rayon Printed Camp Shirt In Pearl, featuring a retro pattern and trendy camp collar, worn casually.
Close-up of Short Sleeve Rayon Printed Camp Shirt In Pearl showcasing retro pattern and fabric details.
Short Sleeve Rayon Printed Camp Shirt In Pearl worn by model, featuring a retro pattern and camp collar.
Back view of a man wearing a Short Sleeve Rayon Printed Camp Shirt In Pearl featuring a retro tropical print.
66% OFF
Quick Buy
Short Sleeve Rayon Printed Camp Shirt In Pearl
$20.00 $60.00
Short Sleeve Rayon Printed Camp Shirt In Sailor Blue worn by a man, featuring a tropical floral print and relaxed fit.
Back view of a man wearing a Short Sleeve Rayon Printed Camp Shirt In Sailor Blue with a tropical leaf pattern.
66% OFF
Quick Buy
Short Sleeve Rayon Printed Camp Shirt In Sailor Blue
$20.00 $60.00
Alpaca Blend Cable Knit Crew in Birch, featuring classic crew neck and rich textured knit in a warm neutral shade.
Alpaca Blend Cable Knit Crew in Birch worn by a model, showcasing its warm, textured design and classic fit.
Alpaca Blend Cable Knit Crew in Birch, back view showcasing cozy texture and classic fit.
Alpaca Blend Cable Knit Crew in Birch worn by a smiling model, showcasing its classic cable knit design.
40% OFF
Quick Buy
Alpaca Blend Cable Knit Crew in Birch
$60.00 $100.00
Men's teddy sherpa pullover in Pageant Blue, featuring quarter-zip and hand warmer pockets, perfect for cozy comfort.
Back view of a man wearing a Teddy Sherpa pullover in Pageant Blue, showcasing its plush fleece fabric.
Close-up of a man in a Teddy Sherpa Pullover featuring a quarter zip in Pageant Blue, showcasing its plush fleece texture.
Teddy Sherpa pullover in Pageant Blue, featuring cozy fleece, quarter-zip design, and hand warmer pockets, modeled by man.
52% OFF
Quick Buy
Teddy Sherpa Pullover In Pageant Blue
$36.00 $75.00
Superfine Corduroy Overshirt in Chipmunk worn over a white shirt, featuring button-flap chest pockets and a classic fit.
Back view of Superfine Corduroy Overshirt in Chipmunk, showcasing its unlined design and classic fit.
Superfine Corduroy Overshirt in Chipmunk featuring a button front and chest pockets.
Superfine Corduroy Overshirt in Chipmunk worn by a model featuring dual chest pockets and a button front.
60% OFF
Quick Buy
Superfine Corduroy Overshirt in Chipmunk
4.0
Rated 4.0 out of 5 stars
4.0
$36.00 $90.00
F245994_ECRU_FRONT.jpg
F245994_ECRU_BACK.jpg
F245994_ECRU_COLLAR.jpg
F245994_ECRU_DETAIL.jpg
60% OFF
Quick Buy
Waffle Texture Quarter Zip Sweater in Ecru
$34.00 $85.00
Detail view of teal mist 6" corduroy cabana shorts featuring side pockets and adjustable drawstring.
Model wearing 6" Corduroy Cabana Short in Teal Mist, styled with matching shirt and casual sneakers.
Model in teal mist 6" corduroy cabana shorts, paired with neutral sneakers, showcasing a classic fit and adjustable drawstring.
Model showcases 6" corduroy cabana shorts in teal mist, featuring a stretch waistband and side pockets.
57% OFF
Quick Buy
6" Corduroy Cabana Short in Teal Mist
$30.00 $70.00
Short Sleeve Rayon Printed Camp Shirt In Orange featuring a lively jungle print and relaxed fit, perfect for summer wear.
Short Sleeve Rayon Printed Camp Shirt In Orange featuring a vibrant tropical leaf pattern and relaxed fit.
Short Sleeve Rayon Printed Camp Shirt In Orange featuring a vibrant tropical print and a relaxed fit.
Short Sleeve Rayon Printed Camp Shirt In Orange showcasing a back view with tropical leaf design.
66% OFF
Quick Buy
Short Sleeve Rayon Printed Camp Shirt In Orange
$20.00 $60.00

Shop the Weatherproof® Vintage sale — premium men's clothing at up to 70% off original prices. Find deals on sweaters, flannel shirts, denim jeans, outerwear, and casual shirts from past and current seasons. Every item on sale is the same quality you'd expect at full price — designed in NYC with premium fabrics and classic American style.

Our sale section is updated regularly with markdowns on customer favorites and seasonal styles. Look for deals on our best-selling Twill Stonewash Sweaters, brushed cotton flannel shirts, stretch denim jeans, and sherpa-lined outerwear. Sizes and colors go quickly, so check back often for new arrivals to the sale collection.

All sale items include the same free shipping on orders over $99, easy returns, and quality guarantee as our full-price collection. Premium clothing doesn't have to mean premium prices — shop the Weatherproof® Vintage sale and upgrade your wardrobe for less.

Shop by Category

Sweaters
henleys
shirt-jackets
Polos
Button-downs
Pants