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How To Dress Casual but Still Look Like a Boss

How To Dress Casual but Still Look Like a Boss

Every morning, we roll out of bed to get dressed, and then we have to fight between two desires—to be comfortable or look hot. On the one hand, sometimes you just have to treat yourself. On the other hand, who doesn’t want to turn heads? We’re here to put an end to the debate once and for all with three words: “Why not both?” That’s right. We’re going to school you in how to dress casual but still look like a boss with our favorite outfit ideas.

For Men

When it comes to building a casual outfit that’s also flu, it’s all about the mix and match. If you get pieces in your head that you know go well together, it’ll be easy to swap them out to keep the look fresh. Here’s a couple of combinations that can’t fail.

Jacket and Graphic Top

On the outside, one of our popping men’s streetwear shirts under a jacket seems like a simple outfit idea. But this is one idea that can spin off into a ton of different looks.


A leather jacket is considered casual. But when people scroll your Insta, that will be the last word they have in mind. This BA biker look exudes confidence without sacrificing comfort. And the best part is you can rock this look at almost any venue, whether it’s the bar or your favorite concert.

Bomber Jacket

Similar to leather jackets, bomber jackets also have a confident, powerful vibe. But what they have going for them that leather doesn’t is the option to crank up the color. When it comes to this look, it often pays to balance your solid colors with your graphics. For example, if you’re rocking one of our Cayman Logo bomber jackets, stick with a simpler shirt.


When in doubt, go back to basics. We all know denim jackets are a classic, casual look that goes with everything, but that doesn’t mean they’re boring. All you have to do is peruse our collection of denim jackets to see what we mean. You can elevate a denim jacket with almost anything: graphics, studs, patches, fur-lined collars. Just remember the balancing act—the louder the jacket, the more low-key the shirt, and vice-versa.

Solid Hoodie, Graphic Pants

In most outfits, all the colors and the graphics happen on top. But even a look as simple as jeans and a hoodie can become the biggest thing in innovation by switching that up. You can get denim jeans that go as hard as denim jackets with graphics, painted embellishments, or patches. Pair that up with a solid-colored hoodie with one of the same colors, and you’ve elevated your look without elevating your effort.

Muted Clothes, Bold Kicks

Sometimes, it only takes a little spark to make a look straight fire. And that spark can be your shoes. Even though a bold, colorful pair of Air Jordans or Adidas can look dope with a matching outfit, they’re electric when they’re the one piece of color in your outfit. Leave the rest of your look neutral—blacks, whites, blues, colors that look good with anything. Then crank it up to eleven on your shoes.

For Women

Ladies, don’t let anyone tell you that you can’t be comfortable while turning heads. The easiest way to dress casual but still look boss is to turn down the volume on your clothes and turn up the volume on everything that goes with it.

Elevating With Accessories


Here’s the thing about jewelry: it makes your every fashion choice look intentional. You could roll out of bed in your pajamas and make it look like a bold, edgy look if you put on a pair of earrings, a chain, or some rings. Keep that in mind the next time you wake up and just aren’t feeling it.


Technically, makeup isn’t an accessory. But it works just like jewelry, telling the world, “Yeah, I know what I’m wearing, and I know it slays.” And don’t resign yourself to minimalist makeup just because you’re going casual. A little sparkle and bold color choices that contrast your clothes are sure to take the entire outfit to the next level.


It’s like we said about the men’s “muted shoes with bold shoes” look: the right pair of kicks can carry an outfit. Usually, the go-to for a fly-casual look is a good pair of sneakers. Although, you can glam up a casual look with some stunning stilettos the same way you can with some bling.

Outfit Ideas

The beauty of having an arsenal of baller jewelry is that you can use it to take any outfit to the next level. But if you’re looking for a few casual looks to get you started, we’ve got you covered.


Tracksuits are the crown jewel of casual clothing—and honestly, a good set of track clothes can stand its ground even without any help. But if you want to take your tracksuit from the gym to the red carpet, try switching out the basketball shoes with heels and add a pair of hood earrings. Zendaya rocked the look at a UK event back in 2018, and we’re still cheering her on.

Boyfriend Fashion

Don’t worry, single ladies. You don’t need a man to rock this laidback casual look. Remember, the goal isn’t to bury your body. You’re looking for an outfit that’s maybe one size bigger than you would usually wear. It’s like you’re borrowing clothes from your SO’s closet, such as an oversized jacket or a pair of baggy jeans. Add a full face of makeup to add a flirty quality to the look.

Crop Tops

You can dress a crop top up or down, but however you rock it, you know you will be the center of attention. For a casual crop top look, rock your top with a pair of jeans or shorts. Then elevate the look as far as you want to take it with glittery jewelry, shimmery makeup, and your cutest shoes.

Every day you get to ask the question—should I look fly, or should I feel comfortable? And every day, you get to look at yourself in the mirror and say, “I should have it all.” Rockstar Original is here to hook you up with all the hottest casual clothing.

How To Dress Casual but Still Look Like a Boss