Types of Shirts - What To Wear and When!

person opening black shirt with beige bra underneath

The market is full of shirts — and we love that! With a million types of shirts, there are a million ways to style yourself. 

Still, if you aren’t familiar with the different types, it can be challenging to know what to wear and when. Not to worry, though; TomboyX is here to help. 

In this post, we’re diving into the wonderful world of shirts to uncover the many different types, styles, and more. So if you’re on a mission to expand your shirt collection and your knowledge of shirts — start here.

The Different Types of Shirts and When To Wear Them

From button-downs and polos to tees and sweatshirts, the guide below will detail the most popular types of shirts and offer advice on when to wear them. Whether you like to keep it casual, dress for success, have a thing for flannel or prefer coziness over anything else, you’re sure to find a shirt to match your taste. Just be sure to shop for good quality once you’ve landed on the type and style to ensure comfort and longevity. 

For the best shirts, we recommend browsing our inventory, where you’ll find eco-friendly fabrics, soft materials, and cool clothes. But first, let’s check out the many different types of shirts below:


Ah, the humble undershirt. This long, knit shirt is fitted and worn under other shirts. Featuring a U or V-neckline, undershirts can add extra warmth when worn; however, the basic purpose of one is to absorb sweat and eliminate visible pit stains.

Additionally, long-sleeved undershirts can make you more comfortable when wearing dress shirts in cold weather. This category can also include tank tops. While tank tops won’t help stop sweat, this sleeveless shirt makes a fashionable statement under an unbuttoned linen shirt or even under a blazer if you’re feeling bold. 

If you’re wearing an undershirt, the fabric should be thin and stretchy so that it doesn’t show through. Opting for TENCEL™ Modal is a sure-winner. It’s soft as cotton, temperature regulating, and kind to the environment. Not sure where to find an undershirt made of this deliciously soft fabric? Check out our TENCEL™ Modal Tank — a soft, casual basic ideal for winding down or layering up.    

When to wear: Think of an undershirt as underwear for your upper body. Wear it underneath your favorite shirts to absorb sweat, keep cool, and stay warm. 


A t-shirt is a piece of clothing that graces everyone’s wardrobe during their lives. From toddlers and teens to adults and seniors, a tee is worn (and loved) by all. It’s a classic fashion statement that goes along with just about everything: jeans, shorts, trousers, skirts, formal pants — the list goes on. No casual wear wardrobe is complete without this type of T-shirt.

When to wear: Whether you have an LGBTQA+ parade to march in, a casual dinner date to attend, or a weekend picnic to enjoy, t-shirts are timeless and never a wrong choice when picking what to wear. Stick with quality like our Perfect Love X Organic Cotton Tee, made with 100 percent organic cotton and lots of love. 


Not to get confused with a sweater or jacket, a sweatshirt is a long-sleeved pullover shirt fashioned out of thick, usually cotton or polyester cloth material. Technically speaking, a hoodie is a sweatshirt with a hood. This cozy garment is a sporty staple worn by style icons for decades now and continues to endure as a spring or fall wardrobe essential. 

When to wear: One of the best times to rock a sweatshirt is when you feel a little chilly and could use some extra warmth. For a laid-back, lounging kind of day, throw on a comfy pair of leggings with your oversized sweatshirt. 

Button-Down Shirt

A button-down shirt is a collared shirt with long sleeves, half sleeves, or short sleeves. Contrary to the popular button-up shirt, a button-down has a button in the collar and can be casual or formal in style. These popular garments come in a variety of colors and patterns, but all have buttons on them — hence the name. 

When styling, keep in mind that most collar types can be worn without a tie in casual settings. The spread collar tends to be more casual, while pleated and cutaway collars are deemed more formal. Each collar variation tends to have a different effect; for instance, the point collar is said to elongate the face. 

When to wear: The button-down shirt is the quintessential work shirt. Typically worn with dress pants or a skirt, this shirt is ideal for professional settings like an office environment. Of course, a button-down isn’t only an office shirt. Different styles (like Hawaiian shirts or excessively loose-fitting button-downs) go far beyond the realm of workwear. 

Polo Shirt

The polo shirt is a classic: It’s a combo of the timeless button-up oxford shirt and the much more casual T-shirt. Originally created for tennis players, this short-sleeve shirt features a soft collar and a placket down the center front with a few buttons.

High-quality polo shirts offer breathability, elasticity, and absorbance, making them an excellent choice for anyone not wanting to compromise on comfort or style. 

When to wear: Want to look put together? Wear a polo. These popular garments are just the right amount of stylish and sophisticated. Match with your favorite casual shorts in the summer or with jeans and sneakers in the winter.

Henley Shirt

A must-have staple in any stylish wardrobe, a henley shirt is a collarless pullover that’s characterized by a placket beneath a round neckline. That said, you can also find henley shirts featuring a V-neck as well as a crew neck. More often than not, this top has anywhere from three to five buttons and can be found with short sleeves or long sleeves.

When to wear: a henley shirt stands out from your basic t-shirt and is a touch more casual than the average polo, making it a great choice for just about any event. Wear it as a standalone top with denim jeans and sneakers or as a warm base layer to keep out the cold in the winter. 

Denim Shirt

A denim shirt is exactly what it sounds like — a shirt made of denim (a sturdy twilled cotton fabric) — and typically features a button-down collar. These popular tops can be ultra-stylish and add a sense of coolness to your look. 

When to wear: Want to keep it casual? Opt for a denim shirt. This piece of clothing can be worn year-round and looks great over a vintage-style or slightly oversized tee. 

Flannel Shirt

If denim shirts are made from denim, we bet you can guess what flannel shirts are made from! Not to get confused with plaid shirts, flannel is a woven fabric most typically made from cotton or wool. What makes flannel so different from other woven fabrics is its “napping,” which refers to the slightly raised texture of the fabric. This coveted feature is what gives flannel its signature softness.

At TomboyX, we’re pretty big fans of all things soft — that’s why we use cozy flannel to make our Midnight Plaid PJ Set. This buttery-soft set feels like a dream and is undeniably perfect for winter lounging. 

When to wear: You can wear a flannel shirt any day of the week with your favorite pair of jeans for an iconic rugged look or chinos if you want to keep things preppy. Or, slip on joggers or yoga pants with an oversized plaid overshirt if you feel like relaxing at home. 

Tuxedo Shirt

The formal shirt you wear beneath a tuxedo suit is known as a tuxedo shirt. In short, it’s a more elegant version of a dress shirt. These button-down shirts can have a spread collar or a formal wing collar, which has a slightly narrower spread between the collar points to accommodate a bowtie. The long sleeves typically have French cuffs, which can be folded back and connected with cufflinks.

When it comes to shirt styles, you have more options. Most tuxedo shirts feature a bib, while some opt for variations like a shirt with a band collar. Not only a men’s shirt, celebrities like Tilda Swinton, Lorde, Jennifer Anniston, and Evan Rachel Wood have all rocked a tux on the red carpet. 

When to wear: This type of shirt is meant to be worn to super formal events, like a black tie dinner party or reception, a wedding, a gala, the opera, or a symphony (you get the idea).  

Wrapping It Up

Truth be told, there are many more shirts to learn about, but they’re way more than we can count! So let this guide serve as a starting point as you navigate the world of shirts and expand your understanding of them. Whether you’re headed to the office, a baseball game, brunch, or even a stroll around the park, there’s a shirt for you. 


24 Ways to Wear Your Tank Tops | Styles Weekly

Collars | University of Kentucky - College of Agriculture 

Evan Rachel Wood reveals why she sported a tux at the Golden Globes | Today

flannel | fabric | Britannica