“Are you really going to wear that?”
Don’t worry, you’re not the only one hearing that. Research shows that the majority of men don’t know the basics of how to dress well. We’re here to help, starting with the most basic garment of them all: the t-shirt.
If you think that all t-shirts are created equal, you might be inflicting some truly bad style on those around you. This article is just for you. Keep reading: we’re about to break down the different t-shirt styles and how to style your t-shirts, so you can take your look from boring to bombshell.
Fitted t-shirts are the original t-shirt style. It dates back to the World Wars when soldiers wore their standard-issue tee undershirts under their uniforms. Later on, stars like Marlin Brando made the sleeved undershirt an emblem of cool, hard-edged masculinity.
Today, the fitted tee still retains an air of athleticism, capability, and adventure.
Our friends at the JasperHollandCo.com tshirt brand make a great case for the fitted t-shirt. A well-cut tee made from resilient, soft material will:
- Stick close to your body, emphasizing your musculature
- Hit at just the right length on your biceps
- Never stretch at the neck
There are no rules about how to style t-shirts when they’re fitted. They’re the go-with-everything staple to populate your wardrobe. If you need specifics, though, try wearing your fitted tee with:
- Dark jeans and a blazer for a cool artsy look
- Khakis and boat shoes for a sophisticated outdoors style
- A sports jacket to achieve a stepped-up athletic look
Any of these outfits will look sloppy with an oversized tee, but a fitted shirt pulls them together.
A relaxed or soft style t-shirt is trickier to style than a fitted one. They may have features like:
- An oversized body
- A stretched neck
- A length that hits far below your hips
Relaxed tees are usually made of a thin, soft material that flows well.
This kind of t-shirt doesn’t have the crisp look of a fitted tee, and it’s not as versatile. That being said, you can still employ it for a variety of stylish looks.
At best, a soft t-shirt says “vagabond chic” or “making Saturday morning look good.” At worst, it looks like something you dug out of the lost and found. Make sure to put enough attention into the rest of your outfit to make it clear that you’re not a sloppy slob.
Still, a relaxed shirt can be the star of a masculine, boho look. Wear them on the hottest summer days with a straw hat, wooden bead necklace, and a touch of leather.
The classic tee is solid in color and has no decoration (except for a pocket on some shirts). Printed tees emerged later. While tricky to style, some printed tees can look great with the right outfit.
As a rule, if you want to dress like an adult, avoid t-shirts with prints like:
- All-over prints (like camo)
- Statements that are trying to be funny (spoiler alert: they’re not)
- Political commentary (we get it, tough guy)
If you choose a printed tee, go for a clean, classic design. This might be an interesting brand logo or an understated design.
How to Style a T-Shirt
Looking for more ways to shake up your tee style? Why not try:
- Tan France’s no-fail front tuck: tuck in the front of your shirt and let the sides hang loose
- Rolling your sleeves a few times
- Adding a layer on top, such as a cardigan, sports jacket, or bomber jacket
- With higher-waisted pants, tuck the shirt in completely
Remember: a t-shirt isn’t going to transform the way you look, the way a well-tailored suit will. When worn alone, t-shirts tend to reveal the extra pounds hanging out at your midsection. These style tips can help distract from imperfections and make your outfit look more cohesive.
Yes, they’re the most versatile piece of clothing in history. However, there are still some t-shirt crimes you should never commit. No amount of style can save you from these t-shirt don’ts.
Wearing the Wrong Size
Never mistake “fitted” for “a size too small.”
A fitted shirt shows off your physique but still looks (and feels) comfortable. A too-small tee looks shrunken, uncomfortable, and overly revealing. A shirt that rides up in the back to give an accidental flash of butt crease — well, let’s just say it’s not going to be a lady magnet.
By the same token, a relaxed shirt gives you extra space, but a too-big tee will drown you. Wearing the wrong t-shirt size will never look good.
Picking the Wrong Material
Looking for a shirt that’s comfortable, casual, yet goes with everything? Then don’t forget to think about the material it’s made of.
Cotton is the gold standard for a great t-shirt. It breathes well and feels soft on your skin. The natural fiber harmonizes with a wide range of styling options, too.
You might be able to get away with a cotton-rayon blend, although rayon is so soft that you’ll lose some of the t-shirt’s structure. A cotton blend might be more comfortable, but you should style it very carefully.
Stay away from synthetic fibers, including:
These manmade fabrics look and feel cheap. Most athletic garments have synthetic fibers, and if you’re headed out for a run, by all means, throw on a synthetic shirt. Just don’t let us — or the ladies — catch you in one any other time.
There’s a Whole World of Different T-Shirt Styles
The Internet boasts an endless variety of different t-shirt styles, from classic to trendy to downright weird. With this article, you won’t be overwhelmed by them. You’ll be able to separate the cool from the kooky and style your tees like a grown-up.
Don’t keep dressing like a kid. If you loved this article, check out the rest of our blog. You’ll learn more unbeatable tips on sharp dressing and classy living.