"Preppy" is a beast with many heads: Southern (fraternities, football), Northern (secret societies, rowing), British (rowing, secret societies), and AC Slater (Zach Morris, nickname). Now, a company rooted in the first three is moving online: Mark McNairy New Amsterdam.
From the North Carolina-born ex-creative director of Ivy-loving clothier J. Press, now e-shoppable MMNA is a full-service prep outfitter that started out making shoes inspired by classic British & American WASP-wear, and manufactured in Northampton, England by Sanders & Sanders, who've been around 137 years, just four less than Deion when signed by the Redskins. Kicks range from the Navy Suede Longwing Brogue (with a "Dainite" rubber sole designed to not leave scuff marks) to burgundy-corrected-grain-leather collabs with Maine's hyper-traditional Bass Weejuns like the Donald, a boat shoe/moccasin hybrid sure to delight T-Pee Pain. Also avail are all-cotton button-downs (from the cheekily striped-'n-solid Oxford Fun, to a denim number so crisp you really could wear it with a Canadian tuxedo) and jauntily formal ties like the Navy/Carolina Blue-striped Jordan, which'll have you batting .497 .202 with the ladies.
The site also vends cargo pants, as well as outliers like cotton-fleece Paradise sweatpants and a pair of single-stitched boxers called "Extra Long, Extra Dope" -- as opposed to "No Hope With Dope", a beast starring (Kelly Kapowski and Johnny Dakota).