He’s always been that way. Even in high school, he pegged his slightly baggy jeans, untucked his shirt just so, and had an easy way of carrying his backpack that made his whole look seem effortless and cool. You never get the idea that he stood in his closet for hours wondering what he should wear — or whether his jeans make his bum look big (for the record, he’s never done either of those things).

When my guy friends ask me about men’s fashion, I often point to him as a model of what I think a boy should wear: equal parts rumpled prep school student and street kid, with a dash of nerd.

Here are a few things that are in his summer rotation:

Tops:

• Polo shirts, $8
• Button-down shirt (in blue and white striped, white or blue), $59.50
• Madras shirts, $95

Bottoms:

• A not-so-baggy khaki, $54
• A not-so-baggy jean, $54
• A thin-legged short, $41.99

Shoes:

• Sneakers, $30
• Saddle Shoes, varies
• Oxford Laceup, $245
• Flip- flops, $22

Accessories:

• A giant watch, $135
• A preppy tie, $45
• Belt, $18

Favorite men’s stores:

• J. Crew
• Urban Outfitters
• eBay

If money is no object:

• Billy Reid
• Band of Outsiders