11 Style Rules for Men to Break Now

By Andrew D. Luecke

You already know wearing white after Labor Day is cool. But menswear is reinventing itself rapidly, leaving some long-held mandates by the wayside, not to mention a bunch of men with a lot of questions. Sure, some style laws are truly inviolable. Showing a quarter-inch of cuff will always be crucial, but with designers and dandies flaunting so many former taboos it's hard to tell what's in play these days. So we thought we'd take this opportunity to let you know which rules no longer apply.

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Rule # 1: Never Button the Bottom Button. This is one of menswear's most cherished decrees. But stylish men have been shrugging it off since at least the early '60s. Ever heard of The Beatles? More recently this phenomenon showed up in Mad Men, a canonical style guide for contemporary men if ever there was one. Now designers are catching up, sprinkling recent runways with this contentious bit of styling. Approach this one cautiously, and try it out with three-button jackets (or even four, but more on that later) only, where the higher gorge will help create a clean military look when you fasten the bottom button.

Rule # 2: Wear a Belt With Belt Loops. This one's borrowed from bespoke suits, where a lack of belt loops is used to display a perfect custom fit. Here, the look takes on an easy-going rebel style that conveys you're too preoccupied with cool stuff (like the beach or, um, women) to remember your belt. Go crazy with this one now, because it's perfect for laid-back summer dressing.

Rule # 3: Match Your Socks to Your Pants. A while back men started showing off brightly printed socks with cropped trousers, a dandified affectation that drew major media attention allover the world. This rule breaker takes that style and builds off it, adding a hint of knowing faux naivety that's right in line with the resurgence of dad style. To make this work, look for the frumpiest socks you can find, in colors like black, brown, or even white.

Rule # 4: Never Wear Pleated Pants. Face it gents, pleats are back, and after years of militant flat front devotees, it's a welcome change. There are two ways to wear this one. The first, the traditional take, works well if your glorious mature physique requires a little extra room, which is actually the original purpose of pleats. Get some pleated suit pants and fill them out. The second, the '50s rocker take, works if you're whippet thin and want to show the world you're no square. Think young Elvis if you go this route. If you're in-between, stick to flat fronts, fellas.

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Rule # 5: No Jackets With More Than 3 Buttons. Ah yes, the four-button suit jacket. This bad boy's long been the domain of NFL analysts who only think they dress well. But the four-button suit jacket has proud history that goes back to England's Mods, an obvious reference for Z Zegna's fall/winter 2014 show. If you like this look keep the jacket slim and the trousers cropped, so the lack of suiting can absorb the visual weight of the extra buttons.

Rule # 6: Always Button Your Jacket. Tom Ford popularized this rule. And though he is right that a buttoned jacket is sliming, his dogma doesn't account for the expressive, free-flowing beauty of an open, draped jacket. This look works best with a double-breasted blazer, but a longer, looser single-breasted jacket works too. If you're going to cross this line, you must ensure that the shoulders fit perfectly and that you're showing the proper quarter inch of shirt cuff.

Rule # 7: Never Wear Black With Blue or Brown. Menswear sages have long held that black doesn't play well with blue or brown, but these guys weren't accounting for the recent joyous resurgence of jolie laide in menswear. This colorful trio is definitely rooted in the '70s, but if recent runway shows are any indication, that's a good thing. When attempting this look, stick to lighter shades, like royal blue or caramel, as navy or dark brown are visually confusing next to black.

Rule # 8: Don't Wear Socks With Sandals. This one's gotten a lot of attention lately, and for good reason. It's not easy to pull off, but if you do, you'll be the coolest guy at the campfire sing-along. Stick to robust sandals, like Birkenstocks, and equally chunky socks. This will ground your look and remind people that even though you're wearing sandals, you're still wearing footwear for fit for a man.

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Rule # 9: You Must Wear Socks. If breaking rule number 9 doesn't suit you, you're in luck, because really you don't even have to wear socks at all, even with suits. There are three ways to tackle this: First, you can wear canvas shoes, which will require nothing more than an occasional spin in the washing machine; second, if you prefer something more formal you can wear loafers or dress shoes, but they must lined with 100% leather, which resists odor. If you go this route also use foot powder in your shoes and let them rest on cedar shoe trees, which will absorb moisture and odor and keep your shoes in shape; Third, you can be a true rebel and wear no-show socks, which will keep your feet and shoes clean without the hassle of washing machines or foot powder.

Rule # 10: Don't Tuck Your Sweater In. Tucking in your shirt is a clear must, but for ages only nerds tucked sweaters into trousers. Apparently we're all nerds now, which is evidently also cool. Designers are smart enough to know this, and voila, recent runways saw herds of models tromp down the catwalk wearing tucked-in crewnecks and even-gulp-cardigans. This rule is actually pretty easy to break-just limit overflow but keeping your sweater slim and your pants high-waisted.

Rule # 11: No Denim on Denim. You certainly can't go full Timberlake, but denim on denim is now a key part of menswear, due to the wide acceptance of denim as the go-anywhere textile of the workwear movement. Many have said you can only pair denim with denim of a different wash, but that's out the window now. Though, if you're going to match tones, do keep the denim dark for formality's sake. If you're going for contrast lighter denim works best because paler washes can look grungy and cheap when matched.

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