Fall/Winter 2025 Collection

Gear up for cooler days and crisper nights with the Fall/Winter 2025 Collection—your one-stop shop for all-new arrivals built for how men actually live. Whether you're layering up, refreshing your grooming game, or shopping smart for the holidays, this collection is loaded with well-made goods that work hard and look sharp.

From heavyweight flannels and cold-weather outerwear to rugged boots, utility-minded grooming products, and durable everyday accessories, each item in this lineup is chosen for style, substance, and season-long staying power.

Pacifica stretch twill overshirt blue and green Baja stripe men’s organic cotton shirt jacket
Sale
Pacifica Stretch Twill Overshirt – Blue & Green Baja Stripe
Marine Layer $84.00 USD $168.00 USD
Men’s jacquard cotton flannel shirt with woven pattern and metal buttons
Sale
Salton Jacquard Cotton Flannel Shirt
Iron & Resin $64.50 USD $129.00 USD
Green striped heavyweight cotton men’s shirt with dual chest pockets flat lay
Sale
Lotus Heavyweight Cotton Shirt for Men
Iron & Resin $64.50 USD $129.00 USD
Jetty Terrace Vest Oyster – men’s insulated recycled polyester vest with nylon shoulders and zip pockets, available at The Simple Man.
Sale
Jetty Terrace Vest – Oyster
Jetty $52.00 USD $104.00 USD
Front view of the Inlet Puffer Jacket in black – lightweight packable men’s winter jacket with zip pockets and quilted Oystex fill.
Sale
Inlet Puffer Jacket – Black
Jetty $90.00 USD $180.00 USD
Men’s Tri-Blend Henley Sweater in light gray with 3-button placket, rib-knit cuffs, and waistband — The Simple Man
Sale
Men’s Tri-Blend Henley Sweater – Classic 3-Button Pullover
Schott $62.50 USD $125.00 USD
BEST SELLER
trellis Cable Pullover sweater in dark brown wool blend, flat lay product photo — The Simple Man
Sale
Trellis Cable Pullover – Dark Brown Wool Blend Sweater
THE NORMAL BRAND $74.00 USD $148.00 USD
BEST SELLER
Men's black quilted vest layered over gray shirt – modern water-repellent outerwear from The Simple Man
Sale
Crest Quilted Vest – Water-Repellent Layer for Everyday Wear
7 Diamonds $70.00 USD $140.00 USD
Bridge & Burn Cole Slim Shirt – Flat lay of striped flannel button-up in navy, brown, and gold tones – The Simple Man
Sale
Cole Slim Brushed Cotton Shirt – Modern Fit Button Down
Bridge & Burn $74.00 USD $148.00 USD
Flat lay of the Bedford organic cotton button-up workshirt in denim herringbone.
Sale
The Bedford Utility Shirt – Denim Herringbone
Bridge & Burn $74.00 USD $148.00 USD
Man wearing a plaid shirt with a white background
Sale
Hero Stretch Flannel Shirt – Maroon, Grey & Tan Knit Button-Down
Flag and Anthem $34.75 USD $69.50 USD
Men's Flag & Anthem Clearbrook plaid flannel shirt in cream and brown, worn open over navy henley – rugged fall style at The Simple Man
Sale
Clearbrook Plaid Flannel Shirt - Men’s Long Sleeve
Flag and Anthem $34.75 USD $69.50 USD
Folded Mountain Overshirt in vintage blue plaid with dual flap pockets and branded buttons—100% cotton heavyweight twill shirt available at The Simple Man.
Sale
Mountain Overshirt - Vintage Blue Plaid Heavyweight Twill Shirt
THE NORMAL BRAND $64.00 USD $128.00 USD
Men’s heavy-duty tan work shirt made from 100% cotton with dual chest pockets and laser-engraved buttons – Horizon Shirt by The Simple Man.
Sale
Horizon Heavy Duty Cotton Work Shirt – Tan
Jetty $53.00 USD $106.00 USD
NEW
Man wearing brushed cotton Red / Black /White plaid button-up shirt with long sleeves and black jeans – rugged men’s fall shirt from The Simple Man.
Sale
Red and Black Plaid Long Sleeve Button-Up Shirt – Brushed Cotton
Liverpool $54.50 USD $109.00 USD
Flat lay of The Larson classic fit button-up flannel shirt in volcanic plaid with chest pocket and button closure.
Sale
The Larson Brushed Flannel Shirt – Classic Fit, Midweight Plaid
Bridge & Burn $74.00 USD $148.00 USD
NEW
The Cole Slim Shirt by Bridge & Burn in Mountain Green plaid shown on wooden hanger, highlighting slim fit and double chest pocket construction
Sale
The Cole Slim Fit Brushed Cotton Shirt
Bridge & Burn $74.00 USD $148.00 USD
Front view of model wearing Generation Plaid Shirt in grey with layered hoodie for fall or winter style
Sale
Generation™ Plaid Shirt – Stretch Comfort Meets Classic Style - Grey
7 Diamonds $62.50 USD $125.00 USD
Man modeling Generation™ Plaid Shirt, standing with arms relaxed, featuring button-front and chest pockets – durable and stylish shirt for men.
Sale
Generation™ Plaid Shirt – Stretch Comfort Meets Classic Style - Oat
7 Diamonds $62.50 USD $125.00 USD
Ritter Flannel Shirt in brown, blue, and tan plaid – men's classic cotton flannel with chest pockets, available at The Simple Man
Sale
Ritter Flannel Shirt – Classic Plaid Cotton Flannel for Men
Flag and Anthem $29.75 USD $59.50 USD
Flat lay of Pacifica Stretch Twill Overshirt in grey railroad stripe pattern, featuring dual chest pockets and durable construction for daily wear
Sale
Pacifica Stretch Twill Overshirt – Lightweight Comfort- Grey Railroad Stripe
Marine Layer $84.00 USD $168.00 USD
Full flat lay of Rodanthe Blanket Flannel in Aloe – long sleeve plaid flannel shirt-jacket made from heavyweight cotton
Sale
Rodanthe Blanket Flannel Shirt-Jacket – Heavyweight Cotton
Howler Bros $62.50 USD $125.00 USD
Voltage Quilted Vest flat lay front view in Bark showing zip front, pockets, and quilted design
Sale
Voltage Quilted Insulated Vest - Lightweight & Water-Resistant
Howler Bros $72.50 USD $145.00 USD
Full flat lay of Howler Brothers Harker’s Flannel Shirt in Kempton Plaid Taupe with long sleeves, plaid pattern, and button front
Sale
Harker’s Flannel Shirt –Taupe - Buttery Soft & Rugged
Howler Bros $49.50 USD $99.00 USD