If you want to get dressed up a little bit, but you don't want to do that whole suit thing, start with a pair of jeans and work from there. Chances are, you're more comfortable in denim than in a full suit. Plus, nothing has proven to be more American or more versatile (fans have included everyone from Andy Warhol to 19th-century miners). To get started, pick up a pair of classic-fit jeans, which haven't changed in decades and will never go out of style. We recommend these Levi's 501s, one of the most iconic products in history because of their timelessness and versatility. Next, add the everyday staples – brown wingtips, a white oxford, and a slim-fitting navy blazer with thin notched lapels. Then – and here's the fun part – introduce a splash of complementary colors with your socks, belt, and bracelet. The result is a refined yet relaxed look that'll have you closing deals at noon and leading the happy hour charge come sundown. Launch Gallery >>
Richer Poorer Socks
Summer Fridays are fading faster than Facebook shares these days, so we've been searching for new and inventive ways to diversify our trusted khaki-and-blazer combo. It's a blessing, then, that we came across Richer Poorer's fun (but not overtly flashy) socks, which brought immediate spark to our everyday workwear.
Nestled halfway between Los Angeles and San Diego in Capistrano Beach, California, Richer Poorer brings all the energy of the left coast without the obnoxious surfer-dude spunk of Jeff Spicoli. We've been logging serious miles in their striped selections, specifically the Po Boy and Walk-On, both of which feature sophisticated eye-catching patterns that'll leave you wondering why you ever sported monotone socks in the first place. We've found them to be lightweight, durable, and, best of all, extremely versatile, so wear them under dark suit pants or light khakis for a flash of personality in the office.
Feeling especially bold on that first post–Labor Day Monday? Flex your sartorial muscles by matching the stripes to your tie. Or, if your confidence is bordering on hubris, kick off your wingtips and rest your dogs atop the cubicle. Either way, your boss will know you mean business. [$12; richer-poorer.com]