The 5 Rules for Mastering a Casual Shirt

The Thomas Crown Affair The Thomas Crown Affair

The 5 Rules
for Mastering
a Casual Shirt

How to make a long sleeve shirt work for you in the dead of summer

Steve McQueen and Faye Dunaway in ‘The Thomas Crown Affair’.

A shirt is perhaps the most important item in a man’s outfit. Pants fade into the background, some shoes will get noticed, others won't but it's hard to ignore a man's shirt when you're looking him in the face. It's a staple, for sure, and one that's highly adaptable. When neatly tailored, crisply pressed and buttoned to the neck, a shirt is merely a staging ground for a formal jacket and tie. But when it's buttoned down, with the sleeves rolled insouciantly, the shirt is the center of attention—a more modern, ruffled and relaxed statement of gentlemanly leisure, understanding and camaraderie. Think of the most stylish men of the 20th century and how their appearance (and appropriateness) was altered by the shirt on their back.

Some men, like Cary Grant or Frank Sinatra, wore tradition quite well. Other men reveled in the freedom that their reputation earned them—guys like Alain Delon, Steve McQueen, Marlon Brando, Montgomery Clift or Mick Jagger became the rebellious bunch that the traditionalists vowed against.

But the differences between the traditionalists and the rebellious were merely in finish. The latter understood the ways of the tidier, they just chose to do it their own way. Think of it like this: a chef trained in traditional French cuisine can surely make a perfect paté, but when the rigorous guidelines of French cooking are absolved, that same chef is likely to make something else, something more palatable and casual, despite having mastered the finer things. This summer, relax a bit and find new ways to wear your collared shirts. Here are a few tricks to finding the right shirt for the not-so-regular occasion.


Todd Snyder Italian Linen Chore Shirt

Italian linen chore shirt,
$228 / $169 by Todd Snyder

Choose the Right Collar

When you're planning on letting the top few buttons undone, it's best to know what collar will look best unkempt. Camp collars are cool, of course. But you want to steer clear of larger spread or rounded collars. I suggest you find shirts you like with a button-down collar with visible or no-see buttons. These buttons (unless your shirt is cut from a light denim, then do without them) will help your collar keep its shape without needing to be buttoned together at all times; a somewhat-structured collar is still a requirement when the shirt is undone to keep you from looking like you're merely jacket-and-tie-less at the moment.

Tackle Your Cuffs

There are plenty of guides on rolling your sleeves—we have a particularly good one ourselves—but the best practice is to do what's comfortable. Like a good fade, keep it tidy and close, but don't worry about abiding by any military-like specifications. Your cuff roll should be unique to your liking and your needs.

Mind the Fabric

The best materials to wear casually, especially in the summer, are inherently light, breathable and somewhat durable. These prerequisites forge a short list of acceptable fabrics: cotton, linen, chambray and light denim; while rayon and silk both outmatch the aforementioned in breezy weightlessness, they don't hold shape nor do they last nearly as long. Your best bet is to seek out a comfortable, cottony shirt to break in and wear it to death.

What to look for in an untucked shirt

Consider the Cut

What to look for in an untucked shirt

You could wear a casual shirt tucked in, but most of the time you'll sport it untucked. Of course, some shirts are simply designed to be worn tucked in. If you wear said shirt untucked, it's both noticeable and sloppy—there's an obvious difference between longline and ill-fitting. Be sure the shirt you're buying, especially if it's online, is modeled untucked. If it isn't, check the length. Compare that length to shirts you own that you know look best tucked in. If they match, don't get that shirt with the intention of wearing it more casually.

Don’t Forget the Confidence

Perhaps most importantly, if you're unsure about your patch of chest hair that shows when you unbutton the top two buttons, don't try this. If you don't feel great about linen or if wearing a long sleeve shirt so casually feels sacrilegious, don't try this. All of the stylish men whom made this look so endearing had one thing in common: the boldness to loosen things up a bit. McQueen surely wasn't worried how many times his cuff was turned over on itself-despite being one of the best dressed men to ever live. Jagger didn't mind skipping more buttons than most men would have dared to. Let this look grow on you and the quirks and qualities of your style will come with time.

This Summer’s
Best Options

Taylor Stitch Ledge Sun Bleached Chambray Shirt

Ledge sun bleached chambray shirt,
$128 by Taylor Stitch

Todd Snyder Favorite Summer Weight Shirt

Favorite summer weight shirt,
$148 by Todd Snyder

J.Crew Baird McNutt Irish Linen Shirt

Baird McNutt Irish linen shirt,
$89.50 by J.Crew

Corridor Shadow Check Shirt

Shadow check shirt,
$165 / $99 by Corridor

Alex Mill Botanical Dyed Mill Linen Shirt

Botanical dyed Mill linen shirt,
$185 by Alex Mill

NN07 Levon Tencel Shirt

Levon Tencel shirt,
$195 by NN07

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