Style

Whatever the job, lifestyle, or style, every guy needs a few staple shirts in his closet. 

A well-curated shirt collection covers all seasons and occasions, providing peace of mind knowing you’re ready for any unexpected event or trip. 

Here are seven comfortable types of shirts and how to style them. 

Crew Neck Tee 

Let’s start with the ultimate classic and the most versatile shirt a guy can have. Yes, we’re talking about crew necks! 

This seemingly humble tee can be everything from your undershirt to an everyday casual piece to a modern substitute for a classic button-down. 

There are various fits, from standard to oversized, and it works for any body type: skinny, pumped, or a little chunkier. You only need to find “the one.” Some awesome options can be found here.

How to style  

Have a few styles and colors you can easily pair with different layers. A crewneck t-shirt looks great with chinos, straight dark denim pants, or even tailored slacks for work and cargo pants, joggers, and shorts for the weekends. 

Wear them on their own or under your favorite button-downs (denim, flannel, chambray). A high-quality tee will work well under a blazer or even a suit. 

Henley shirt

Don’t have a Henley shirt yet? It’s high time to get one because it’s a great way to mix things up without compromising comfort. 

Henleys can be long-sleeved and short-sleeved, with a few buttons and a plaque going down the collarbone. 

This tee style is a little more casual than your crewneck, with some exceptions, such as cashmere or thin merino wool, that ooze luxury. 

A classic cotton Henley is usually made from thinner fabric and highlights your chest and shoulders well.

How to style 

Generally, long-sleeved Henleys are better for layering and short-sleeved tees for wearing on your own, but we’re not the boss of you. 

This shirt has a rugged feel and looks fantastic with cargo pants, flannel shirts, denim jackets, and work boots. 

You can also elevate the look and style your Henley with chinos, an unstructured blazer, and leather sneakers.

Polo shirt

Polo shirts have made quite the comeback, though they’ve never really gone away. The difference now is that you don’t need to be over fifty and have a golf club membership to wear one! 

Polos are the perfect middle between a regular shirt and a tee. The collar makes you look more put-together; our only advice is to go for a fitted style instead of the baggy 90s one.

How to wear 

The fun thing about Polos is that even the brightest colors are very much welcome. The best is to have a couple of shirts in classic shades you can pair with your chinos, blazer, and loafers s and then have fun with bold colors like e.g., purple for vacations, linen pants, and espadrilles. 

Oxford shirt

Even if you’re not into formal wear, you need an Oxford shirt because you never know when you’ll get invited to a wedding or other formal event. 

Finding the right fit is the secret to looking good in such a shirt. It shouldn’t be too tight or too baggy so that you can wear it on its own or under a suit or a blazer. 

You want the right sleeve length, enough space around the collar (not too much), and freedom of movement.

How to style 

Wear your Oxford shirt under a suit or a blazer, layer under a cardigan or cashmere jumper, and pair it with tailored pants or chinos. Style it with off-white trousers, boat shoes, and a trench coat or unstructured blazer for a more relaxed look.

Flannel shirt

While flannel may remind you of lumberjacks, it’s not really a bad thing! 

It’s a versatile and comfortable piece you can dress up or down depending on the occasion. 

A flannel shirt is perfect for winter and colder weather and is a staple you’ll find yourself reaching for all the time. 

Flannel shirts come in a variety of colors and patterns, so you’ll definitely find one you like.

How to style 

For casual looks, pair your flannel shirt with jeans, cargo pants, sneakers, or worker boots, and throw on a denim or leather jacket. 

Dress up by styling the shirt with dark denim, chinos, wool pants, blazers, and Chelsea boots.

Linen shirt

Just as flannel is a cold-weather staple, so is linen a summer one. 

Perfect for the beach and the city, it can be casual or smart-casual and is very comfortable.

Pure linen is very wrinkly, so if that bothers you, get a linen-cotton blend. 

There are a few styles for your selection, from long-sleeved and short-sleeved button-downs to pullovers. 

How to style 

You can’t go wrong with linen or cotton pants, shorts, Birkenstocks, or Tom’s shoes. 

A linen shirt looks good on thin denim and white or off-white cotton trousers too. 

Remember that you don’t have to stick to white linen. Branch out to salmon, sky blue, and sage. 

Hawaiian shirt

Some may say Hawaiian shirts are not must-haves, but we beg to differ. They’re comfortable and cool and add a twist to the simplest outfit.

The key is getting a Hawaiian shirt that doesn’t look like a part of a costume. We recommend opting for more subtle patterns and never compromising on quality. 

Another important thing to remember is the fit. While oversized shirts are fine, you don’t want to look like you’re drowning or are about to move to Florida. 

How to style 

Style a Hawaiian shirt with solid bottoms, from khaki, olive, or navy shorts or cotton chinos to brown cargo pants. 

It’s best not to mix different patterns, so avoid printed jackets and bottoms and stick to monochrome pieces. When it’s warm, wear your Hawaiian shirt on its own, and if it’s getting colder, throw on a simple denim jacket.

You can also wear the shirt unbuttoned on a simple tee. The most important thing is to have fun and not be afraid to experiment!