Chicago Manual of Style—04/28/09

What are the standards for men’s fashion? The question becomes even more mind-boggling when it comes to dressing for spring and summer temperatures. Ultimately, it seems that looking great is a matter of self-confidence and intuition.

By Jessica Hester

There’s a question that’s been bothering me ever since President Obama was criticized by some conservative circles for sitting at his desk in the Oval Office without a suit jacket: What are the standards for men’s fashion? For me, the question becomes even more mind-boggling when it comes to dressing for spring and summer temperatures. Sure, men can go shirtless and wear jean shorts and flip-flops. But should they?

Fashion-forward women know that new trends spring up each season. Wearing last year’s tough gladiator sandals with this year’s demure Liberty print floral dresses is a faux pas. While I know how to forecast seasonal trends for women, I’m totally clueless when it comes to guessing how men should dress for the warmer weather. I turned to stylish third-year Sam Chereskin to help lay down some ground rules for looking cool as the weather warms up.

I’m an advocate of eschewing seasonal trends in favor of creating a personal style. The guys seem to be with me on this one. Chereskin points out that while the style of women’s clothing changes every season with fleeting trends, men’s style is consistently based around a set of timeless styles and cuts. “Usually, seasonal iterations by designers only reflect variations on a theme,” Chereskin says. He favors brands like Kenneth Cole and Calvin Klein, who both produce tailored, tried-and-true staples that can be mixed and matched to create a look that marries casual comfort with elegance.

Summer is synonymous with sandals, but flip-flops can’t go from beach to boardroom. While they’re totally acceptable when you’re lounging outside, sandals look totally out of place when you’re leading a presentation. If you’re wearing a dress shirt and pants, you’re too dressed up to be wearing flip-flops. If you work in a creative environment where employees dress down in jeans and T-shirts, you might be able to pull off simple Havaianas in basic black. Otherwise, go conservative in leather loafers and super-low socks.

Even if you know where to wear sandals, you still face the considerable problem of figuring out how to wear them. There is no scenario in which the combination of socks and sandals is anything other than a misstep. As Chris Rovy, fashion correspondent for the style-savvy website, points out, the point of wearing sandals is to air our your feet after a long, sweaty, stinky winter of being shoved into thick socks.

On a scorching summer day, it’s tempting to want to show some skin. When it comes to shorts, how short is too short? Don’t flash any thigh. “Almost all men’s shorts options, I think, exist in a two-inch margin of error around the knee. I tend to wear shorts at it or above it,” Chereskin says. Calf-length shorts look sophomoric and skater-boy, rather than sophisticated. Chereskin also suggests that if you’re going to show some leg, you should make sure you’re choosing a classy fabric. Linen or khaki shorts are great options, but “denim shorts are a no on all occasions,” Chereskin says.

To tuck or not to tuck? How do you wear summer shirts without looking sloppy? “Don’t tuck in your t-shirt without an overshirt,” Chereskin says. Tucking in a polo shirt is advisable only at a country club. If you’re not on the golf course, stick to styles that don’t require tucking. Stores like the Gap and Old Navy sell affordable, body-conscious crew neck and v-neck shirts that look polished without looking too preppy. For a sleeker look, you can tuck in a button-down, but “you need a good-looking belt to make it work,” Chereskin says.

While I still don’t fully understand the reasoning that the President needs to be wearing a suit and tie in order to convey respect for the weight of his job, I am starting to get a grip on the politics of men’s fashion. Ultimately, it seems that looking great is a matter of self-confidence and intuition. “I feel that being well put together, or well dressed, is as simple as making sure that you are wearing your clothes and that they are not wearing you,” Chereskin says. That attitude is always en vogue.