Chesapeake's Military and Workwear Style
The Chesapeake's brand was born in 1987 during a trip along the East Coast of the United States. In the Chesapeake Bay—after which the brand is named—a naval battle of fundamental importance in the American War of Independence took place in 1781.
This Italian brand draws inspiration from the vintage world, particularly American outdoor and western military garments, as well as European workwear from the 1930s. Chesapeake's also offers other popular items such as the M-51 jacket, N-1 deck jacket, and fatigue pants, all inspired by military history.
Military jackets are overwhelmingly favoured by men over 40 as outerwear that accentuates masculinity. There are many types of military jackets—such as the MA-1, M-65, and N-3B—ranging from authentic vintage and surplus pieces to modernized styles from high-end and streetwear brands. In this article, we focus on the military jacket, highlighting key styling points, the latest international men's outfit inspirations, and recommended items.
Military wear has had a significant influence on men’s fashion and is now widely adopted for everyday use. However, classic pieces like olive green, khaki, and camouflage field jackets—especially vintage and authentic styles—require thoughtful styling to make them work well in a modern, urban context. While there are commercial models designed for the civilian market, and fashionable interpretations by designer brands, pairing these jackets with clean white pants or raw/washed denim is often the key to creating a refined and cohesive look.
To balance the ruggedness of chambray western shirts, white pants, olive green and khaki military jackets are particularly effective due to their strong neutralizing power. The sharp contrast adds a sense of cleanliness and elevates the look, transforming the military jacket from utilitarian outerwear into a sophisticated everyday piece.
Chinos with a center crease are another great option for achieving a more mature and polished appearance. They pair especially well with military jackets, offering a balance of masculinity and elegance while creating a calm, composed aesthetic. Discover our selection of the finest Chesapeake's pieces.
