A simple t-shirt delivers an endless count of stylish outfits, and yet it’s too easy for us to wear the same outfits over and over. We can drop the habit, however, and that’s what this list is for — to help you venture out of your usual rotation without totally leaving your comfort zone. At Fresh Clean Tees, it's no secret we love a good t-shirt. So here are 20 ways to style a t-shirt this year.
1. T-shirt, blue jeans and sneakers
This is such a simple outfit, and you can mix and match it with no end in sight. Switch it up by wearing any shade of t-shirt, whether a crew neck t-shirt or a v-neck t-shirt, as well as basketball shoes, flats, or running shoes of any color. This is the most casual outfit on the list, since you can wear it on dates, with friends, to school, out grocery-shopping, and so on. Style doesn’t have to be complicated, and this outfit makes that clear.
2. T-shirt, black leather jacket, black jeans, and black sneakers
This is a classic look that never goes out of style. A leather jacket with a white tee and some black jeans? Add some sunglasses and you’ve got that eternally rebel look, seen on a ton of smooth operators, from Danny Zuko to Fonzie. Even if you don’t own a bike and aren’t in any musicals or running a diner scene, this is a quintessential look. Even The Ramones rocked it at a constant. In fact, magazines like Esquire go out of their way to list the best leather jackets of the year, and the lineup always includes variations of this standard. There’s also endless sightings of celebrities in this combo. Sure, this is one of the outfits on the list that you can’t really mix and match too readily, but it’s forever a killer option for a night out. This outfit is the epitome of looking past fashion trends and discovering a style that never dies out.
3. T-shirt, black denim jacket, black jeans, and flat sneakers
This is quite the alternative rock star look. Seriously, think about all the times you’ve spotted Green Day’s Billie Joe Armstrong or Foo Fighters’ Dave Grohl rocking this outfit. How could it not be fashionable? Hell, maybe even paint your nails black and add pins to your jacket while you’re at it. Just make sure that it’s not too hot out when you wear this one because you’ll absorb way too much heat.
4. T-shirt, short-sleeve plaid shirt, chino shorts, and slip-on boat shoes
For men, fashion becomes a bit harder in summer. Winter definitely spoils us with fashion choices and outfit lineups. I mean, think of the endless count of jackets you can rock in colder temperatures compared to your options for tops when the sun’s crashing down upon you. With winter, you’ve got puffer jackets, leather jackets, bomber jackets, and the like. In summer, well, you’ve essentially got t-shirts, short-sleeve shirts, and tank tops. Never fear, though, as this outfit is a solid go-to if you’re looking to enhance your summertime style. With endless colorway options, you’ll never run out of combos from this simple collection of mix and match.
5. T-shirt, flannel button-down, ripped jeans, and flat sneakers
You don’t have to be from Seattle to (hard) rock this outfit. The quintessential grunge lineup is and always will be good to go. Since the 90s, however, this outfit’s essence has changed quite substantially. It’s no longer associated with the loud and arguably angry demeanor of the grunge era. Rather, more commonly now, this outfit is seen amongst clean-cut, casually dressed dudes. This is another outfit that you can mix and match to eternity, and it’s a pretty cool one to wear when going out for a cup of coffee or a nice springtime stroll in the park.
6. T-shirt, blazer, chino pants, and oxford shoes
When I think of this outfit, my mind almost instantly goes to guys on movie sets — you know, producers, directors, and the like — not to mention all the actors persistently caught wearing this outfit in paparazzi shots. Maybe you’re in, or breaking into (or dreaming of breaking into), the movie industry yourself. If so, this outfit is perfect for you! But even if you aren’t rubbing elbows in Hollywood, this combo is great for events such as business meetings, job interviews, and even weddings (where you may steal the show).
7. T-shirt, wool or velvet sports coat, blue jeans, and oxford shoes
This outfit is common amongst professors and celebrities alike. As an academic myself, this is one of my favorite go-tos. There’s something strikingly sharp and thoughtful about this look. It may be because I see so many professors wearing this. You don’t have to be a professor or a celebrity to nail this look, though. It’s just a solid upgrade for business casual without venturing into formal.
8. T-shirt, joggers, and windbreaker
Wearing an open windbreaker alongside a matching set of track joggers and a t-shirt is not only stylish, but it’ll also keep you comfy as the seasonal weather shifts. While this outfit is best suited for springtime, it can be quite good for lounging indoors, whether during summer’s hottest days or winter’s coldest nights. This is actually a great look for outdoor adventures as well. On hikes, I’ve noticed that cotton might not be the best call, as a cotton-polyester blend is typically the best of both worlds. Do right by your body.
9. T-shirt, chino pants, zip-up hoodie, flat sneakers, and sunglasses
This is becoming quite the urban look. I guarantee if you go to any of America’s biggest cities right now, you’ll spot a lot of people wearing this outfit bolstered by a zip-up hoodie. It’s particularly common amongst college students, and its components have been included in GQ’s wardrobe essentials for men this year. Rest assured, this outfit is youthful and in fashion.
10. T-shirt, chino shorts, slip-on boat shoes, sunglasses, gold chain, and gold watch
This is sort of like the summer version of the above. It’s infinitely customizable with different colors of shirts, shorts, shoes, chains, sunglasses, and watches. The accessories certainly don’t have to be gold. They can be any color you like, depending on the other colors you’ve already incorporated.
11. T-shirt, jeans, basketball shoes, and baseball hat
This outfit is a New York classic. There are endless basketball shoes and baseball hats to choose from for an eternally rotating flavor. Having lived in New York, I’ve seen so many combinations of this outfit, all of which always look comfy and cool while having been in style for as long as I can remember.
12. T-shirt, brown leather jacket, blue jeans, and flat sneakers
I’ve always found this outfit to be so relaxed, confident, and stylish. It offers complimentary colors between the lighter leather and the blue of the jeans, as opposed to its all-black equivalent. Given the less dominating color scheme, this outfit can withstand cool weather, making it awesome for fall and early-to-mid spring.
13. T-shirt, bomber jacket, jeans, and combat boots
I love bomber jackets. You can wear them in just about any weather, many of them are waterproof, and they look badass. What’s not to like? They’re such a simple addition to an outfit and yet they can make all the difference. One strange thing about bombers, though, is that I’ve been mistaken for someone in the military several times when I’ve worn mine. It did, after all, originate as a military flight jacket. However, I don’t let this deter me and neither should you!
14. T-shirt, pleated shorts, drivers, sunglasses, and a watch
This is another look for summer, especially if you’re a bit older. It’s just timeless. You can mix and match it with no end in sight. Each item of clothing in this outfit is typically produced in an endless spectrum of colors, so you can never really run out of combinations. This outfit is particularly good if you’re heading into a daytime date or an informal business meeting and the weather is quite sunny. It also works well for your everyday activities. It’s just solid.
15. T-shirt, long-sleeve thermal shirt, jeans, and sneakers
This outfit is for anyone carrying around a healthy dose of nostalgia for the early 2000s (especially if you were into Blink-182 back then). Looking back on the era, it’s pretty wild to realize how commonplace this look was. Depending on where you are now, you might notice it’s still pretty common. Hell, even Brad Pitt rocks it. These days, it’s more of a lounging or day-off outfit. Personally, I like to wear it out on walks or grocery shopping. It’s super comfy and it just feels right, you know?
16. T-shirt, denim jacket, joggers, and running shoes
We all have errands to run, and checking off to-dos isn’t really the time to care how fashionable you are upon stepping out. You’re merely trying to get from Point A to Point B, and due to our stringent legal system, you can’t head out in your underwear, no matter how hot it is that day. Joggers and running shoes are supreme for errand runs, since you can quickly slip them on — and a denim jacket is appropriate (and straight up cool-looking) for most climates. Voila! Your outfit for much ado about nothing!
17. T-shirt, peacoat, chino pants, oxford shoes and a scarf
Peacoats are a handsome addition to any man’s wardrobe. This is especially the case if you live in the city, as it becomes an essential article of clothing for you to own. This outfit is best for cold weather, since peacoats are generally made of rather warm wool. I personally like to wear this outfit when I’m doing something particularly luxurious. For instance, wear this if you’re going to brunch at a nice restaurant, a museum, or the theater. It’ll give you a sense of presence and conviction.
18. T-shirt, basketball shorts, and basketball shoes
Once again, speaking as a New Yorker, this outfit is pretty standard, and it combines comfort and performance when you need it. I’ve worn this while going out with my girlfriend, hanging out with friends, and heading out to the gym. It’s a go-to ensemble, especially when you’re in a rush. Basketball shorts are easy to slip on and you can find so many different colors of them. Same goes for t-shirts and basketball shoes, so you’ll never run out of elements. You can add a zip-up hoodie as well. I especially like to do this when I’m just lounging at home or going for a thoughtful walk.
19. T-shirt, long coat, black jeans or chino pants, and oxford shoes
Long-coats are elegant. That’s just a fact. It’s almost like you get to wear a cape, but in socially sanctioned fashion. This outfit is confident and intellectual, and it’s great to wear for dates, library drop-ins, and such. This look might suggest you’re pursuing a persona, but it’s honestly just a comfortable, chic look that’s got self-respect written all over it.
20. T-shirt, flat-front shorts, sunglasses, boat shoes or loafers, and a watch
Here’s a fancy yet simple outfit for summer. Mix and match this one to your liking, and you can wear it on a date, to an informal business meeting, out with friends, and so on. It’s a breezy approach to classy, and it’s versatile in its ability to fit the context for which it’s worn. Just don’t step onto any golf courses if you’re not a golfer: you might be mistaken for one of the country club’s regulars.
What I love about these 20 outfits is just how much you can do with each and every one of them. T-shirts may be basic, but they make the best building block. They’re the first step toward countless fashionable outfits. There’s no reason to complicate your approach to style. These are so simple and sharp; you’ll be upgrading your whole look just by knowing a few tricks.
— Daniel Lehewych
