51 90s Hip-Hop Fashion Inspirations

As 90s fashion continues to be in resurgence, it only feels right to show some of the cooler ways to dress for the current trends. When done right, fashion lives on forever, regardless of whether certain items are considered “trendy” or not. Take a look at some of our favorite ways to style these classic pieces.

1. Air Jordans

Jordans are always in style and you can’t convince me otherwise. Whether you choose to rock a vintage pair or one of the newer releases, these kicks have a built-in swagger that can be seen from a mile away. Jordans look good with just about anything, from a classic t-shirt and jeans combo to a more streetstyle flair. It’s all about confidence – if you feel good, you look good.

2. Clarks Wallabees

If you’ve ever donned a pair of Clarks Wallabees then you know just how comfortable they are. Sometimes you have to choose comfort over style but not in this case. 

Wallabees are a classic for a reason. They’re easy to wear and easy to style. If you have Wallabees in the standard colorway, keep it simple with a chambray button-up shirt and black jeans. For a black pair, nothing looks more effortless and put together than styling them with a pair of distressed denim jeans and a black shirt, whether it be a t-shirt or a cool black jacket.

3. Coogi Sweaters

Easily one of the most recognized patterns of all time, Coogi sweaters and cardigans are here to stay. Although jokingly referred to as “Cosby sweaters,” Bill Cosby never actually wore anything from the brand Coogi. His sweaters were typically styled with pleat-front khaki pants, but that is not how the cool kids do it.

The beauty of a Coogi sweater, besides the beautiful colors and pattern, is that they can pretty much go with anything. Wear them with jeans, blue or black, and with your favorite pair of sneakers or Timberlands. Bonus points if your kicks are as bright as your sweater!

4. Double Denim

One of the most famous denim-on-denim outfits to date has to be the infamous 2001 Justin Timberlake and Britney Spears (Free Britany!) double denim red carpet look. They did not embody the 90s hip-hop era or fashion in general and their stylist should’ve been fired. 

Double denim can go really bad or really right. A cool way to wear this trend is a pair of denim overalls over a neutral t-shirt. To up the hip-hop factor, undo one of the upper buckles and throw on an open chambray button up and a pair of retro Jordans. Finish off the look with a few rad accessories – sunglasses, bandana, or watch – and wait for your style to be emulated. 

The secret to double denim is to not be so matchy-matchy with your denim washes, include a neutral piece of clothing, and pair with cool kicks and accessories. For more inspiration, just check out #doubledenim on IG.

5. Dungarees

Nothing screams 90s hip-hop quite like Dungarees paired with a pair of Timberland boots. Enough said.

6. Luxury Tracksuits

Luxury tracksuits are all about two things: brand and fit. You can wear a Gucci tracksuit all day but if the joggers aren’t fitted or your top is too loose, it’s a no-go. Keep it simple with an easy sneaker.

A white pair of Air Force 1s or black adidas Gazelles will do the trick. Keep accessories minimal as well. A great watch or simple gold chain is all you need. Let the apparel speak for itself.

8. Military Apparel

Was military apparel ever really out of style? I say not! You can choose to rock this trend in many ways. First, with camo print. Wear a camo pant/shirt combination with a pair of clean white or black kicks. To break up the camo, wear a white t-shirt underneath that hangs out just enough to appeal to the eye.

A pop of red also looks really cool with camo. Wear a red baseball hat and a pair of classic Jordans (callback!). Or, if you don’t want to be as obvious, stick to military-esque hues, such as military and olive green, khaki, black, and white. Throw on a vest or parachute pants to really up the 90s factor.

9. Oversized Clothing

Oversized jeans (think JNCO brand style), oversized t-shirts, and oversized jackets. Wear one or two or heck, wear all three!

Bonus points if your t-shirt is actually from the 90s. Logo or sports shirts tend to work best for this style if you’re truly trying to keep with the 90s theme. Dr. Dre’s 90s style is the perfect inspiration for this look. He paired most of his looks with Timberland boots and looked fly as hell. Iconic.

10. Paisley & Bandana Prints

The secret to wearing paisley and bandana prints? Keep the rest of your look simple. Black or denim jeans, a neutral t-shirt, maybe a Members Only jacket, and a clean solid pair of sneakers or boots will be your canvas. Throw on a bandana, whether on your head, tied around your neck, or on your wrist, add some swagger, and away you go!

11. Plaid and Check Flannel

Plaid and check flannel is how I dressed in the 90s. I was very into the grunge scene and I still have not given it up to this day. One of my favorite looks is a pair of black joggers, a black t-shirt, white Air Force 1s, and a red and black buffalo plaid button up shirt wrapped around my waist. 

Just like with the paisley and bandana prints, if you’re wearing plaid or check flannel, let that piece of clothing be the standout and build the rest of your look around it. A more hip-hop look would be a pair of oversized dark denim jeans, a neutral t-shirt, and an oversized button up worn open with a pair of Timberland boots.

12. Puffy Jackets Outfit

Puffy jackets have stood the test of time for a reason. They are light, yet incredibly warm, and are straight-up dope (to use a popular 90s term). And they are easy to style. 

Wear your regular streetwear look and throw a puffy jacket over it. Just don’t zip it or button it up. Unless you’re legit wearing it for warmth. If you’re wearing it for fashion’s sake, leave it open. Black, white, and red is always the classic combination, but keeping your look tonal looks just as cool and fashion-forward without trying too hard, which is the ultimate goal.

13. Starter Jackets and Caps

If you don’t remember the Starter jacket and hat phenomenon of the 90s hip-hop era, well then, I just feel sorry for you. I remember my brother begging my parents for his first Starter jacket and when he finally got one, I was so incredibly jealous. I would sneak in his room when he wasn’t there and wear it, imagining how I would style it so much better than him.

It honestly doesn’t take much – again, a pair of dark oversized jeans and a white t-shirt are the perfect underpinnings to pull off this look. If you’re not into the oversized thing, a regular pair of blue or black denim jeans or even a pair of Dungarees will have you looking fly as you represent your favorite team with your Starter jacket and hat.

10. Timberland Boots

Timberland boots are 90s hip-hop personified. Really. You can pair these classic boots with any of the above looks and you have instant 90s streetwear style. No exaggeration.

Timberlands and Coogi sweaters? Check. Timberlands and double denim? Check. Timberlands and luxury tracksuits? Check. Timberlands and military apparel? Check. And the list continues – Check, check, and check.