With such a keen eye for design, it’s little surprise Ralph Lauren’s personal fleet of cars has earned accolades and commendations from around the world.

But come Labor Day weekend at Lime Rock Park’s Historic Festival, five of the finest examples from RL’s garage will make an appearance.

The guest list:

’64 Ferrari 250 LM

Ferrari250LM-2

Ferrari’s first mid-engined car is highly coveted on an average day. RL’s particular LM was piloted by, then rookie, Jackie Stewart (the ‘Sir’ came later).

’53 Morgan Plus Four Flat Rad

Morgan Flat Rad

One of 750 Flat Rads made. Ralph saw fit to swap the original engine for a “more powerful” 90 hp Triumph engine.

’29 4 ½ liter Birkin Bentley Blower

Bentley Blower

Easily the most storied car in the group. Ralph’s Bentley actually took second place in the 1930 French Grand Prix,

’56 Jaguar XKSS

JaguarXKSS

Immortalized by the King of Cool, the XKSS is instantly recognizable. RL’s is in fact one of only two converted from an original D-Type.

’59 Porsche 718 RSK

PorscheRSK

One of 35 RSKs ever built. It’s an icon that went on to inspire and influence designers for generations. We can see why Ralph picked one up.

via Architectural Digest

—Bryan Campbell