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How to Dress up a Classic T-Shirt

By ShirtSpace | Aug 23, 2019 |  Updated Feb 27, 2024

When day turns to night and weekdays turn to weekends, you may find yourself in need of changing up your look. But, after a long work week, what if you just want to throw on your favorite t-shirt and be done? Below are some tips on dressing up your classic tee so that you’re put together, comfortable, and ready for a fun night out with friends.


If you’d prefer to wear a pair of jeans with your tee, you’re in luck! There are a few different ways to dress up and pull off your look while keeping it cool in your jeans.

First, one great option is a pair of boyfriend jeans and a blazer. This look is understated, yet trendy and comfortable. With your classic t-shirt VS a more feminine dressy blouse, this look says “Who, me? I woke up this way.”

Another great option with jeans, is tucking in your top and opting for a cute pair of heels over your standard casual flats. Tucking in your top creates a more finished look and the heels really pull your look together. To really put your look over the top, consider a black pair of jeans and a leather jacket. Talk about a statement!

Lastly, another go to option for jeans, is a pair denim flares. This creates a different silhouette and is even better when matched with a trendy tuxedo blazer and sassy heels. This look is perfect from day to night and season to season!


For a dressier look than your favorite pair of jeans will give you, there are multiple skirt options that are super cute when paired with a classic t-shirt.

One amazing skirt option is a striped cotton skirt with a pair of chunky- heeled sandals. This is a fun summer look and can be spiced up with graphic tee or bold colored print. Either way, it’s a breezy, relaxed look that’s easy to pull off.

Next, a slit skirt and lace up heels is similar to your striped cotton skirt, but is a bit spicier and more fashion forward. The slit adds some flare and the right pattern can really elevate your look. Should you choose a pattern skirt, opt for a solid top so that your look isn’t too busy. If you go for a graphic tee, choose a solid slit skirt to help balance your look.

For an extra bold ensemble, a leather mini skirt with edgy heels is the ticket. This is perfect for an after hours night out on the town!

For something sweeter and a bit more girly, opt for a floral pencil skirt with a t-shirt knotted in the front or half-tucked in. The t-shirt downplays the girliness, but the floral pattern still allows for a softer look. Pair this look with some strappy heels and your look will be on point!

Finally, a whimsical fringe statement skirt is a great option to couple with your classic tee. Less is more on top when you’ve got whimsy on the bottom!

As you get ready for a fun night of doing what you love, just remember to be comfortable, confident, and don’t be afraid to get creative. It’s actually quite difficult to ruin a look with the right classic tee, but hopefully the tips above will help you avoid any unexpected fashion blunders!

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