Joseph Krauss is a photographer, musician and lover of all things art/creative. "I've always loved the way things look, be it a picture, landscape, or an outfit being worn. I'd say I’m an emotional dresser; I love things that remind me of a person, place or even a space in time." Joseph got into style when he was young, having grown up listening to a lot of rock music and having siblings in the gothic/mall rat era. "I was obsessed with seeing how their cool older friends expressed themselves through their clothing, green hair, tight striped pants, 90s baggy skate style–no rules

"I gravitate heavily towards brands like J. Press where 20 different people could wear the same brand and all express themselves differently, be it more preppy, or classic ivy. Personally, I love a crafty-ivy look, which is why I picked out these pieces. One of my favorite sweaters is J. Press' cotton crew. I’ve worn holes into it now and it only gets better with age. Speaking of emotional dressing, the jean jacket was chain stitched by one of my very best friends @rangerstitch (on instagram). I left the jacket at his house on total accident (or was it calculated?) and when I went to pick it back up a couple weeks later, he had totally pimped my ride with my name, a floral design and the words ‘ring my bell’ on the back with a big liberty bell 'cause I’m from Philadelphia. Thanks J. Press and the wonderful Laura Arnold for having me come play dress up."

Al Culliton is a transmasculine writer, historian, and bartender. At present, they mostly write about the American Cocktail and the culture around it from the eighteenth century through the mid-twentieth. Al lives in the hilltowns of western Massachusetts, where they enjoy the perfect mix of olde New England charm and robust queer community. Their current favorite bar is their little village’s tavern, the Conway Inn, established 1860. You can find them tending bar two or three nights a week at Gigantic in Easthampton, MA.

“I grew up in Brighton in the '90s and spent a lot of time in Harvard Square as a teen. I'd walk the brick sidewalks reveling in a sense of time travel, popping into Leavitt & Peirce—to smell the pipe tobacco and peruse the old-man objects—and then into Bob Slate to stock up on pens and stationery. On my rounds, the old J. Press shop on Mt. Auburn Street always caught my eye. I loved to peer through the old window-panes at the handsome sweaters and suits styled so beautifully—'twas certainly an early influence on my enduring love of classic American sportswear.

*note: that's not a typo in Leavitt & Peirce! Weird spelling of the latter surname (and the former, for that matter!).”

Based in Connecticut, Matthew Longcore is the founder of the Preppy Handbook Fan Club which was featured in The Wall Street Journal and has a loyal following on social media. Matthew grew up in the preppy environs of Westport, Connecticut. He works for an anthropological research organization based at Yale University and teaches anthropology at the University of Connecticut. Currently he is a Ph.D. student at Salve Regina University in Newport, Rhode Island working on a dissertation about Collegiate Gothic architecture.

“I discovered The Official Preppy Handbook in the late 1980s and loved the description of Trinity College, one of the top 20 preppy colleges – ‘Uniformly Preppier, students here embody good-looking, devil-may-care-ism.’ I later attended Harvard and Yale for graduate school, making it impossible to root for one team at The Game. I am a member of Cedar Point Yacht Club in Westport and enjoy sailing on my boat, Swift. I appreciate the timeless and nostalgic aspects of Ivy style and preppy culture. I would describe my personal style as collegiate and nautical, so I feel right at home in madras and seersucker. J. Press, aptly described as ‘Old Guard’ by the Preppy Handbook, is naturally one of my favorite brands.”