Rules, as they say, are meant to be broken. And, at the very least, to be bent. That is especially true when it comes to men’s style rules. There was a time not that long ago when the only choices available to a guy were whether to wear a navy or a grey suit with a blue or a red tie (before such decisions denoted political affiliations).
Thankfully, those times have past and men have a huge palette to choose from, not just in terms of color, but garments as well. Today, it is not only OK to wear sneakers to work, but it’s acceptable wear a plethora of different styles, from minimalist Common Projects to retro Air Jordans. While a tie is no longer requisite in most workplaces, it is still a way for a man to express his personal taste. But now guys are moving beyond silk to elegant knits and wools that have a more modern feel.
Still, certain style rules persist. Not wearing a belt with suspenders is one that will endure for generations because it is both a redundant and a ridiculous look. Square-toed dress shoes are going to be a no-no for the foreseeable future as well. But there are plenty of antiquated style rules that you should feel free to break with impunity. And if anyone calls you out on it, just tell them they’re old rules don’t apply to you.
Rule No. 1: Your Shoes Should Match Your Belt
This is a holdover from the times when both items came in only two colors: brown and black. Today there are lot of options based not just on color but on fabrication. A grosgrain ribbon belt, for example, looks eminently sharp, but you’re never going to find a pair of shoes in the same color. The same holds true for that pair of Nike ID sneakers you just created. But even in the original case, black and brown are not mortal enemies. If you’re going to break this rule, start out with a brown belt and black shoes. It’s a little easier to pull off than the opposite iteration. What’s more important is that the style of each item work in concert. Pair formal belts with formal shoes and casual belts with casual shoes and let the colors fall where they may.
Rule No. 2: You Shouldn’t Wear White After Labor Day
This one is just B.S. all the way around. Show me a guy in white jeans, suede Chelsea boots and a camel overcoat and I will show you the coolest guy in the room. Any room. Some historians speculate that the rule originated from rich aristocrats who were able to escape the city for the country in the summer and wore white to delineate the change of environment and because it was cooler. Darker clothes, according to this explanation, were to be worn in town after summer had passed. Today white should be looked at as an elegant color that brightens up an outfit, and oftentimes, your mood 12 months a year. Even when they get a little dirty, white jeans still look cool and the white button down has always been a year-round staple. You may have a little trouble keeping your white sneakers summertime fresh in the colder months, but that just gives you a good excuse to pick up a new pair when the seasons change back again.
Rule No. 3: You Should Never Wear Pleated Pants
This is a newer addition to the list. Pleats used to be the industry standard in suit and dress pants. They created a little bit more of a striking silhouette. But flat front pants took over for the last 20 years or so because they had a more minimal design that was appropriate for both formal and casual settings. But make no mistake, pleated pants are making a comeback. Noah, the menswear brand from former Supreme creative director Brendon Babenzien, has a great pair. And guys are recognizing that mixing a more traditionally tailored bottom with a more laid back top can work to great effect, so you no longer need to fear the fold.
Rule No. 4: You Shouldn’t Wear Black and Blue Together
If you think the only time black and blue go together is when you get a bruise, think again. A navy sweater with black pants, or vice verse, is an incredibly refined look. The subtle difference in tone between the two colors creates an added layer of depth to an outfit that is missing in a strict monochromatic look. The other proof that black and blue work together is that it passes the sneaker test. Look at the black and blue “Royal” colorway of the Air Jordan I. It is one of the most beloved versions of one of the most beloved sneakers. If it works on a pair of sneakers, it probably works on the outfit as a whole.
Rule No. 5: You Shouldn’t Carry a Bag
Forget all that “murse” noise. Guys have stuff and that stuff needs to be transported. Hence the need for a bag. And the options available to guys today are abundant. From tote bags to duffel bags to backpacks, from leather to canvas to wovens, there are countless ways to carry your laptop or gym clothes in a way that feels masculine and stylish. Plus, toting around a bag is good for the environment because you’ve always got some place to stash a lunchtime toothpaste pickup instead of having to use a landfill-destined plastic bag.
Rule No. 6: You Shouldn’t Tuck in Your T-Shirt
This is “another one” (DJ Khaled voice) that is new to the list. Tucking in a T-shirt used to be a clear indicator of dorkiness. Lately though the tuck has been adopted by everyone from cool skaters to A$AP Rocky and it’s reclaiming some of the cool it had back when icons like James Dean kept their T-shirt hems securely underneath their waistbands. Getting the proportions right is key when breaking this rule. A baggy shirt with slim pants can make you look bloated. But a slimmer shirt with more relaxed pants captures that ‘50s swag.
Rule No. 7: You Shouldn’t Wear Socks with Sandals
Admittedly, coming to terms with breaking this rule took a bit of time. For years, the sandals and socks look was associated with that old dad at the beach scanning the sand with his metal detector. But as slides-style flip-flops and Birkenstocks have emerged as more year-round footwear, the style ban on socks with sandals has eased. The key is getting the socks right. If you’re rocking some Adidas slides, go with a pair of modern athletic socks. If it’s Birks on your feet then a chunky wool sock with a creative pattern is your best bet. Either way, make sure that your hosiery is CLEAN.