why this works: of course it helps if you are model slim and good-looking, but done right, oxford + khakis + loafers = very stylish. (done wrong, you look like you work in IT.) hedge your bet by choosing a pink shirt over the traditional white or blue, and pair it with slim pants maybe a shade darker and browner than the standard chino. try going sockless, cuffing your pants and wearing a (slightly) more colorful ribbon belt — with a look this simple, the details make all the difference
why this works: the slimmer pants balance out the boxy shirt jacket (although keep in mind there’s no way to make clothes that just plain don’t fit look good.) as discussed previously, the earthy brown shoes and bag (and hardbound book) warm up the cool blues and blacks of the rest of the outfit, and the colorful plaid peeking out hints its wearer isn’t always as serious as he looks.