Reddit reviews A Privileged Life: Celebrating Wasp Style (Icones)
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Assouline
There are so many fantastic books about the lifestyle. These are a few that are fashion/dress oriented:
Ivy Style
True Prep (update version of preppy handbook)
The Official Filthy Rich Handbook
Official Sloane Ranger Handbook
The Big House: A Century in the Life of an American Summer Home
Theory of The Leisure Class
Brooks Brothers. Generations of Style. It's All About the Clothing
A Privileged Life: Celebrating Wasp Style
Lacoste: The Element of Style
How To Be A Gentleman series