Fit is Foremost
Lead with the Shoulder
And when it comes to fit, she explains, "The shoulder is everything – in shirts and in suits. If the shoulder is too big, then the suit's too big, period. The rest can be tailored, but the shoulder can't. So it's always a good idea to dress a man from the shoulders."
Simplicity is Key
"You don't have to look like you're trying so hard," advises Pink. "Just because you see it in a men's magazine doesn't mean it's going to work on you – not everybody should be in a skinny-cut jeans, for example. This is especially true if you're not an uber-fashion guy."
Choose the Right Shoes
Although pairing running shoes with a pair of khakis and a polo has become universally accepted silver-screen shorthand to indicate the "fashion-challenged male," Pink is quick to point out that sneakers aren't necessarily off limits. "There are some that might work – like Converse hightops or these suede Pumas that are out right now," she says. "They'd be perfect with a pair of jeans or khakis."
Accessories After the Fact
"All the little things make a difference," Pink says, "Yes, the shoes but if you're wearing a ring, if your belt's nice, your bag — what you carry is as important as what you wear."
Pink points out that knowing when to forgo the accessories is equally important, and points to the final scene of "Crazy, Stupid Love," in which Carell's character gives a touching speech wearing a simple white dress shirt and a gray Ermenegildo Zegna blazer, sans necktie.
"When we were doing his fitting I was thinking about going with an Etro tie," she explains. "And Steve was the one who suggested we get rid of the tie. It was like a light bulb went off, and it fits where his character has gone by the end of the movie."