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Upgrade your wardrobe: 6 essential types of shirts every man needs

From button-ups to sweaters, here are the best of the best

Man having a drink
The Manual

Ahhh, the shirt. The bones of an outfit, the bread and butter, the megaphone of your style. No matter your style, there is always the question of what shirt you should wear. When you are dressing up, when you are casually running errands, going on a first date, or doing chores around the house, the shirt is what people notice. It is how you communicate who you are and what you want from life. As a matter of fact, there may not be any garment in your closet and on your body that is more important than your shirt.

Wearing an expensive suit and wearing the wrong shirt will ruin the entire look. Wear the same suit every day? As long as you change the shirt, many people will focus on the shirt more, not even noticing the suit. The point is, you must wear the right shirt all the time. There are no days off in this particular category of style. With that in mind, we want to ensure you understand the types of shirts you choose from and that you pick up these six that will transform your wardrobe today.

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The dress shirt

Button-up shirts on hangers
Nimble Made / Unsplash

The dress shirt is as old as time. While it used to have frills at the collar and has gone through many changes, the modern dress shirt is the most important shirt you will have for your elevated wardrobe. It can take denim and a sportcoat to the next level and work in tandem with a suit to ensure you’re always taken seriously. There are a couple of things to keep in mind when shopping for the right dress shirt.

  • Get the color right. You want to pick up as many white ones as you can, followed by some light blue, and then branch out into different colors and patterns.
  • Get the collar right. The collar you wear will be directly related to the shape of your face, where the right one stays on the right side of style.
  • Get the fit right. Like everything on this list, the fit is vital. Ensure the collar is fitted, but you can fit two fingers between it and your neck when it’s buttoned. Make sure the cuffs show about 1/4 an inch under the suit sleeve.

The polo

Man in striped polo and brown pants
Alejandro Alvarez / Unsplash

The polo is a staple in the man’s wardrobe. It is the number one shirt for men in the summer and is not going anywhere anytime soon. While it was first conceived in India for polo players in the 1800s as an alternative to the shirt and jacket look, it evolved and developed to be worn in other sports, such as tennis and rugby, ever since. Today, polo shirts are the pinnacle of style and have four different variations for your closet.

  • The short-sleeve pullover is the most common version of the polo, as it is the most closely related to the original and was made famous by tennis players.
  • The long-sleeve pullover is very similar to the short-sleeve pullover, but extending the sleeves makes it more appropriate for winter.
  • The button-up polo is a great vintage option when you want to add a little depth to your wardrobe. Cut like the polo but featuring a button front, it’s a great marriage between the button-up casual shirt and the short-sleeve pullover.
  • The rugby polo is similar to the long-sleeve polo but is more casual and usually features a more sporty design reminiscent of the ones worn by rugby players on the field.

The sweater

Man wearing sweater in the woods
Jose P. Ortiz / Unsplash

Since the days of keeping fishermen in Ireland warm and dry from the harsh ocean, the sweater has been a favorite among men everywhere. They run the gamut on size, style, and price, so when you begin shopping for a sweater, there is much to consider. You can go with a thinner merino wool that feels dressier and perfect to layer under a suit. Or you can go for the chunky and cozy sweaters meant for watching movies or having coffee on the porch. Either way, here are a few options depending on your style choices.

  • The button-up cardigan differs from the sweater only in that it slides on like a jacket. It is the number one back porch or fireside option, elevating anything you wear immediately.
  • The cable-knit is the original Irish creation that screams cozy comfort and will likely be stolen by your partner often on those cold Netflix nights.
  • Turtlenecks are a stylish option when you’re looking for something different to jumpstart your style. Wear them as a statement or under a jacket — either way, they won’t let you down.
  • Opt for a V-neck sweater if you want something that will go great over that dress shirt. If the V is done right, it can be worn by itself, but if it cuts too far down, it’s not suitable.

The henley

Man in sunglasses and henley
KC Stone / The Manual

The henley is the hardest-working item in your wardrobe. It is also the most underrated shirt. Cut like a long-sleeve tee with only a few buttons on the front, it has numerous ways to be worn. While it comes in basic cotton or wool, some waffle-knit and other variations give this shirt texture and life. Here are the three best ways to wear a henley.

  • As a base layer when you want to stay warm, style this shirt under a button-up and roll the sleeves to give it a hard-working look and a masculine aura. For an example, see Tom Cruise as Jack Reacher.
  • Wear it as the statement of your outfit. If it’s the only shirt you’re wearing that day, opt for the waffle-knit to make a statement.
  • Finally, wear it over a dress shirt like you would a sweater and elevate your outfit with something a little different.

The button-up

Man in jeans and white button-up shirt
Oktay Köseoğlu / Pexels

Finally, we get to the shirt that will dominate your closet: the button-up. This kind of shirt is such a broad category that we are going to break it down into a few different subcategories to make it a little more digestible. So here are a few ideas for a button-up shirt.

  • The casual button-up consists of a shirt cut like a dress shirt but made of softer cotton. More casual patterns, like plaid and stripes, make this shirt perfect for wearing with jeans or chinos.
  • The sport shirt is between the above casual shirt and the dress shirt. While it has the patterns of the casual shirt and oftentimes the same fabrics, it typically has a button-down collar that makes it perfect for wearing under a sport coat.
  • The short-sleeve button-up is the summer option to the casual button-up. Usually, it will have the same patterns and fabrics, although there are lighter, breathable options to keep you cool in the summer.

The flannel

Man in graphene flannel
The Manual

Last but not least, we come to the flannel. While this shirt could have been added to the above category of the button-up, we feel that the flannel is a big enough wardrobe staple that it deserves to be recognized on its own. You can thank the Welsh and their ingenuity in using leftover sheep’s wool to create a soft and warm fabric for their new shirts. The result is one of the manliest shirts in your wardrobe. Whether you work in construction or crunch numbers as an accountant during the week, once you slide this thing on for the weekend, you become the manly lumberjack overnight.

There are dozens more shirt options for your wardrobe, from the tee to the linen shirt, but these are the basics of the shirt wardrobe and are the easiest stepping stone to beginning a killer shirt collection.

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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