Becoming a man's a delicate dance of experimenting with bold ideas and ultimately rejecting them -- which is why you now wear socks with your loafers. For gear that entertains influences without embracing them, try Surface To Air.
Started as a New York art collective, the most obvious trend among S2A's line of graphic tees, polos, slacks, etc, is an affinity for the '80s tempered with a New Millenium understanding that breakdancing is very, very hard. Their sweaters offer the bold "big stripes" look, but V them to reduce the convict/bumble-bee effect; meanwhile, their merino knit cardigans look like what Mr. Belvedere would've worn when he was busy courting nannies, and not being one. Their Bomber Jacket (made w/ an abrasion-resistant nylon used to sheathe Army blades) pulls the grandest trick of all: it allows you to rock a Member's-Only look, without looking like a member.
The accessories part with the nostalgia, but not the noncommittal-ness, e.g., die cut aluminum and silver rings are scaled-down versions of their brass cousins, covering only 2-3 knuckles, leaving your pinkie exposed -- so you can flirt with the bold idea of fighting, while still properly enjoying your tea.