Sometimes even the most posh pieces of clothing may look like snaffled from a charity donation, but it only increases their awesomeness for the real men, right? Touted as tailored for the Isle of Man TT motorcycle race, Freemans Isle of Man jacket comes with an 8.5 oz wax cotton shell and 100% milspec melton wool lining for warmth. It’s wind and water resistant, and also equipped with heavy duty zippers. Offered by the Freemans Sporting Club, this cool Isle of Man jacket is made in NYC, priced at $489.