After a few trips with my Signature Duffle in hand, I offhandedly mention to Clegg that I would love to see it in a smaller size. I think selfishly I just want to carry my bag not just on weekend getaways but every day. Not long after our conversation, Clegg makes short work of what is now his Small Signature Duffle. The new overnight bag, featured here in chocolate*, is ideal for overnight trips or just daily jaunts to the gym.

At $765, the Small Signature Duffle is a far cry from an impulse buy. But you don't really want that in a heirloom piece. You want something that you can aspire to. You want something that is going to sting a little. And Clegg offers that at an incredible value. See, Frank Clegg sells his bags directly to his customers. If he didn't, Bergdorf Goodman would be peddling them for upwards of $1300. And that is probably why Clegg doesn't allow that, the hard working American that he is. He understands the value of craftsmanship and that of a dollar...even if it stings.

*courtesy of Frank Clegg Leatherworks

Connecticut style (right) and Maine style (left) lobster rolls ($16)

Red Hook Lobster Pound specializes in fresh catch lobster. Susan Povich and Ralph Gorham, who founded the seat-of-your-pants operation in 2008, drive up the coast of Maine several times a week to round up their crustaceans. They serve up rolls in Maine (chilled lobster, celery, house mayo, light spices) and Connecticut style (warm lobster drunk on butter). In a moment of indecision I order both. Nine minutes later, no regrets. It is easily one of the best lobster rolls in New York (and I’ve had Lunch before).

I pop into Murray's Toggery Shop, the birthplace of Nantucket Reds, to pass some time before my buddy Jon Terbell and I begin building out his summer pop-up shop, One Orange. It's what one would expect from a small town sportswear clothier. But after I wander into the back room (where there is everything you could ever imagine in Nantucket Red) I notice a small stash of Boast piqué polos hanging in the corner. While certainly a fan of the brand, their fit left a little to be desired since I last pulled on the "Japanese Maple Leaf" a couple years ago. Rumor had it Boast revisited their polo's fit* recently and I secretly hoped it to be true. The arm holes are higher, the body sits closer to the torso while the tennis tail hits at just the right part of your backside. I happily left with one in Carolina Blue. Back in play, as they say.

Never heard of Boast? Enjoy this animated abridged history of the irreverent squash inspired sportswear company to get up to speed.

*It would seem as if Boast embraced vanity sizing as where I was once a medium, I now wear their small (I'm 5'11", 175lbs)

They were musing about style. And while style is what you have and not what you buy, it remains elusive to most men. This sartorial pandemic can partially be attributed to most men’s lack of style icons—individuals or characters (past and present) you are drawn to. Personal style starts there though...icons. Amanda Brooks sums it up perfectly when she observes, “Style does not come to you unless you pay attention to it.” It is something one develops through a constant looking process. That looking process will be in vain though if you’re closet is full of clothes your mom or ex-girlfriend picked out for you. Icons of Men’s Style can help you with that. The thorough encyclopedia examines the most important menswear staples (the duffle coat, the polo shirt, the penny loafer, the diving watch, etc), their provenance and history, the stories of their design, the brands that started it all, and how the iconic pieces shaped the way men dress today. Now you can know, and knowing is half the battle.

Photographed in New York, NY

Noteworthy: Ray-Ban aviators, monogrammed engine turn buckle, Lazyjack Press tie. Patrick is one of the founders of Lazyjack Press, a men's accessories brand that embodies Italian luxury and an American sense of humor.]]> ]]>

Listen on Spotify

Photographed in Brooklyn, NY

Noteworthy: Levi's 501s, Saint James tee.

Photographed in New York, NY

Noteworthy: town (scalloped dress) & country (cotton canvas field jacket) mix, ginger hair. Mackenzie runs Design Darling, an online boutique for girls and women.

Iconic look: Dark suit, white shirt, tie

Key accessories: Bow tie, Leica rangefinder

Thing you can't imitate: His photographic eye