The Rules and How to Break Them: The Irreverent Button-Down Collar

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The world of menswear is full of rules. Many of them are old and seemingly inconsequential, but they do exist for a reason. Knowing the rules helps you dress correctly. Knowing when and where to break them is a mark of true style. The button-down collar shirt, a staple in American menswear, is a great place to start in understanding this idea. Here are five ways to wear one: One right way and four “wrong” ways.

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The Correct Way

The button-down collar has its origins in the world of sport, like so many of the small details of menswear. Originally worn in England by polo players, the idea was to keep the soft collar points from getting in the way when riding horseback, hence its old name the “polo collar.” As such, its “correct” setting is in casual outfits with other country derivatives. With a tweed jacket, corduroy trousers and other such less-than-formal combinations, they are perfectly correct, tie optional.

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The Wrong Way #1: With a Business Suit

Given the leisure origins of the button-down collar, it’s no surprise that it’s technically incorrect to wear one with a  business suit — but it happens all the time. A particularly East Coast American convention, the button-down collar can soften up the formality of a suit just enough, though in many places it is still considered glaringly incorrect, so tread carefully. This looks best with a simple white, blue or even pink button-down, but we are talking about breaking rules here, so feel free to get adventurous.

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The Wrong Way #2: With a Double-Breasted Jacket

A double-breasted jacket or suit is largely considered to be inherently a bit more formal than its single-breasted cousin. For that reason, wearing one with a more casual button-down collar is strictly forbidden by the mandates of fine dress. However, some of the most stylish men in recent history have often reveled in breaking this sacrosanct rule. A double-breasted navy blazer with the right button-down collar can be particularly striking. As with pairing a button-down with a suit, be careful and make sure not to pull this trick in situations where it would still be inappropriate.

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The Wrong Way #3: Unbuttoned

Obviously, those buttons are there for a reason and should be fastened. Breaking this rule is great for achieving an especially laid-back feel. Try a button-down collar shirt in a rougher fabric like a heavy oxford or rugged chambray and leave the points free. Worn with or without a tie, it’s a great look with a burly tweed jacket and dark denim jeans.

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The Wrong Way #4: The Pinned Button Down

This is by far the most egregious affront to the “rules,” and in some ways the most fun. Wearing a collar pin on an unbuttoned button down is a look rarely seen. First and most famously done by Fred Astaire in the 1930s, then re-popularized by Polo Ralph Lauren in the 1980s, it’s a “devil-may-care” look like no other. Best used in very casual settings, save this one for times when you’re wearing a tie purely by choice. It’s fun with a jacket and jeans, and can be toned down a bit by adding a sweater on top.

Occasionally breaking the rules can be a great way to add a dash of extra style when needed. But always remember, you have to know the rules in the first place, why they exist, and what they mean in order to break them successfully.

Photo credits: An Affordable Wardrobe

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