Style Secrets: How to Find the Perfect Shirt

a man wearing a button up

Every man needs a shirt that is the perfect fit. | Pablo Cuadra/Getty Images

The perfect shirt is a staple in any stylish guy’s wardrobe. It can add some personality to your office attire, elevate your style at formal events, or enable you to look put together with limited effort for more casual occasions and weekend events. You probably have a good idea of the colors and patterns you like in your shirts — but the modern man has many more ways to communicate his personal style (and his knowledge of menswear traditions) than simply his shirts color or pattern.

With more choices in shirt style and detail comes more confusion over what’s appropriate for everyday, casual occasions, and formal events. So let’s start with the basics: What’s the difference between a dress shirt and a sport shirt? A dress shirt, generally speaking, will be a more conservative style and color than a sport shirt. Dress shirts typically have stiffer collars, which enable them to accommodate ties and pair well with suits. Sport shirts are more likely than dress shirts to be patterned, and sport shirts’ patterns tend to be bigger and bolder than the more discreet motifs of more formal shirts. Another easy way to tell the difference? Dress shirts are sized either by the neck and sleeve length, or just the neck measurement, while sport shirts will usually come in sizes like small, medium, and large. If you don’t know your size, get measured.

Folded colorful dress shirts in closet

Folded colorful dress shirts in a closet. | iStock.com

The most important distinction between dress shirts and sport shirts is the fabric of which the shirt is made. A dress shirt will generally be made of a lightweight, fine cotton, in weaves like broadcloth, twill, or pinpoint oxford. A sport shirt, on the other hand, can feature a more rugged weave of cotton in a standard oxford or flannel, or a lighter, less-formal fabric like a cotton chambray or even a linen.

When shopping for a shirt, you should first figure out whether you’re looking for a dress shirt or a sport shirt. With that out of the way, figure out the kind of fabric you’re looking for. Do you want a solid shirt, or one with a small, office-appropriate pattern? Do you need something to make a bit more of a statement for a party or a wedding, or are you going all-out casual and looking for a pattern that can really broadcast your style without the limitations of dress wear?

Dress shirt collar with stripes

Dress shirt collar with stripes. | iStock.com

For many guys, choosing the perfect shirt often comes down to the choice of fabric. But it never hurts to know more about other important features of a shirt, like its collar. Collars come in a number of different varieties, all of which are appropriate for different occasions and in different ensembles. A button-down collar falls at the more casual end of the collar lineup. Many men opt to wear them with a blazer but not with a full suit, in a nod to tradition, while others follow the lead of modern designers and magazines and do wear them with a formal suit and tie. A point collar features a narrow space between the points of the collar, and should always be worn with a tie, since the points appear too long when the top button is left undone.

A spread collar features a wider expanse of space between the points of collar, and pairs well with a Windsor knot. Look out for numerous variations on the style, such as the semispread, English spread, or the abbreviated spread, which is a smaller version that can be worn either with the top button undone and under a blazer, or buttoned and paired with a tie. A cutaway collar is the widest of collars, and looks best styled with a tie with a wide knot. Traditionally, the rule has been that the wider the spread of the collar, the more it needs a tie and the wider the knot should be. However, the goal is for the collar and tie to achieve a balanced look together, so a narrower knot can work just as well for some guys.

A man putting on his perfect shirt

A man putting on his perfect shirt. | iStock.com

A club collar is primarily considered a novelty, and as such, isn’t a style to wear in most conservative workplaces. A snap-tab collar, a style that’s been popular on and off since the 1920’s and 1930’s, features tabs that fasten beneath the knot of the tie to hold the points of the collar in place. Like the club collar, the snap-tab collar is considered a novelty, and falls on the sporty, rather than formal, side of the collar lineup.

And finally, a note on cuffs: The button cuff is the most common type and can come with square, round, or angled corners. The more formal barrel cuff has two or three vertical buttons. The turnback cuff is the middle ground between the button cuff and and the formal French cuff. If in the process of shirt shopping, you realize that your shirt of choice for the occasion at hand has French cuffs, then it’s definitely a dress shirt. Use cufflinks accordingly.

colorful shirt collars

Colorful shirt collars folded over. | iStock.com

The fit of your shirt should be largely the same whether it’s a dress shirt or a sport shirt. If you aren’t familiar with a brand or with the specific cut of the shirt that you’re considering purchasing, you should really try it on. You’re looking for a tailored, flattering cut that both comfortably accommodates your shoulders and is trim throughout the torso. Many brands offer a modern slim fit and a more generously cut classic fit, and it’ll pay off to try a couple of sizes in several fits to determine which comes closest to looking like it was made for you.

When trying different sizes, also make sure that the collar fits; you should be able to fit one finger between your collar and neck. If two fingers fit, the collar is too big. Sleeve length is also important, and when unbuttoned, the cuff should reach just past your wrist. If you’re considering a shirt that you plan to wear both tucked and untucked, make sure that the end of the shirt falls no lower than the bottom of your back pocket. Dress shirts can fit longer than sport shirts, since the extra length makes it easier to keep them tucked in. And whether you plan to tuck in a shirt every time you wear it or are purchasing one that will never be tucked, make sure it lies close to the body through the waist and hips. You don’t want lots of extra fabric to deal with, and a billowy shirt is flattering on nobody.

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