Men’s Shoes Trends from the 90’s

Man wearing blue 90s preppy boat shoes
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Last Updated on February 21, 2022

Have you ever found yourself trying to decide which pair of shoes to slip on?

Now imagine it’s 1999. You were an early grunger, a mid decade preppy and ended the era with sneakers that gave Maurice Greene a run for his money.

The 90s was choc-a-bloc full of different styles of footwear.

Some dressed in a preppy manner. Some in grunge. Others as skaters, the athletic types, the hip-hop fanatics, the ravers, and many others.

Let’s take a look into these cultural groups, and the 90s shoes trends they preferred.

The Ivy League: Shoes in the Preppy Subculture

The preppy subculture was associated with individuals who attended private schools, universities that represented the more ‘traditional’ aspect of American society. This was of course reflected in the way they dressed.

Boat Shoes and Moccassins

Preppy styles in the 90s primarily consisted of boat shoes or moccasins

These could be worn with, or without socks, though usually were styled without. While the preppy subculture was a minority during the laidback 90s, the group still existed but stood out from the most popular trends of the decade.

University students from the Northeastern part of the United States, attending prestigious schools such as Harvard, Yale, and Princeton, were often seen wearing them.

A quick walk around any of these campuses would prove the fact that these were a huge trend among a selection of people, you can buy Sperry boat shoes on Amazon here. A popular shoes brand that produced these styles of were Clarks with their Wallabees design—a hit among the preppies. 

The great advantage of these style of shoes is that they are timeless; they can still be worn today and represent a sense of simplicity yet elegance that can match with many different styles. Modern versions are produced by shoes brands like Sperry’s, such as this classic design

Tennis shoes

Why tennis shoes? You may know them like sneakers, athletic shoes, gym shoes, running shoes, and the likes, but the truth is they are all pretty much the same thing. 

Originally, tennis shoes were created to provide the British Navy with shoes that didn’t slip on deck and they became widely available around 1892 (marketed as “plimsolls”). Later on, they were adopted on the tennis court, because they wouldn’t damage the court and were super comfortable. 

The difference between tennis shoes (used for tennis play) and athletic shoes (your good old sneakers) is mainly of a technical aspect. You can get sneakers everywhere, but proper tennis shoes, that provide the necessary support and can withstand the strain a tennis match exerts on the shoe and athlete, are a specialty item. They are usually shock absorbent, have lateral support, have less cushioning and are made of sturdier materials. 

Nike Air Resistance II

During the 90s, Nike was the king of the courts with its Nike Air Resistance II model. The second edition of this iconic model featured Kevlar on the toes and had a hard body box that protected the foot. They were launched in 1996 and came out with a warrant, they were that indestructible!

Nike Air Oscillate

Their second runner-up was the Nike Air Oscillate, which came out during the same year. They were famous for being the shoes that Pete Sampras used when he won his Australian Open, and he continued to be a loyal fan for many years. They had a synthetic upper and a mesh tongue for a tighter fit. Also, the midsole featured Zoom Air cushioning, which made them one of the most comfortable tennis shoes of all time. 

Nike Air Challenge LWP

If you were wondering, Nike also held third place with its Nike Air Challenge LWP. This model had a suede upper with copper mesh that was both durable and breathable. The shoes also featured dual Nike Air units in a Phylon sole that created a lighter shoe that responded better to explosive movements (as is often required in tennis). This model was also super popular in basketball circles.

Read: A Go-To List of 90s Brands

Anti Establishment: Shoes in the Grunge Subculture

The grunge subculture during the 90s was heavily influenced by rock bands such as Nirvana, Alice in Chains, and Pearl Jam. These bands helped society reject the past ideas of formalwear and popularize and informal take into everyday clothing.

Combat Boots

Black, lace-up, combat boots were a big symbol of the grunge look during the 90s. These shoes were for the most daring of people, since they made a statement, and could be quite intimidating.

These were preferred by die-hard rockers, who were into tattoos and rave music. Eddie Vedder, the lead singer of Pearl Jam, was famous for wearing black combat boots, with thick, white socks.

Dr. Martens was famous during the 90s and still is today, as one of the highest sellers of the classic black boots. Modern versions of the products can be purchased here. These shoes are very grunge aesthetic and are not for everyone since they represent a very particular fashion style. 

The footwear of choice varied between Converse sneakers and chunky combat boots. These were known as the typical old school shoes of the 90s.


Converse sneakers were the preferred choice of footwear for the members of many alt-rock bands, who were often seen wearing them both on and off the stage. They usually opted for black and white Chuck Taylors … and the dirtier the better!

Black and white became the most popular Converse colors of the decade. Converse continues to be a trend, especially in the white color shade. While they are very informal, even in comparison to other sneaker brands, they are highly unique. They are and always will be iconic.

Modern versions of Converse still look awesome and I recommend buying Converse Hi-Top Sneakers from here.

Read: Top 10 Brands Like Converse (For Every Look & Price Range)

Gnarly Footwear in the Skater Subculture

Skate culture was a prominent aspect of society during the 90s, especially among the youth. The name is a given; these people’s favorite activities revolved around skateboarding.


The shoes of choice were usually Vans sneakers, worn with thick socks. These became a sort of uniform for this subculture, and are still highly representative of skate culture today. 

Matt Hensley was one of the famous skaters during the 90s—and was always seen skating with his Vans on. Not only were the shoes considered cool, they also provided adequate stability and comfort during the sport.

Vans are still selling consistently and can be found in many different varieties, I love these black suede canvas style Vans. The preferred version was the classic low tops style.

While Vans are very comfortable and practical, they are extremely casual due to their material and over all aesthetic. They represent skate culture well and are difficult to style with most other subcultures. 

Read: 25 Vans Shoes Alternatives that make Perfect Gifts

Sneakers in the Athletic Subculture

During the 90s, chunky sneakers became a huge trend. Different interpretations featuring color variations and size differences were created, but the overall idea was the same. The chunkier, the better.

The athletic subculture, associated with sports fanatics and casual devotees, favorited Adidas, Nike, Puma, Fila and Reebok as the popular athletic shoe wear brands of choice. 

Adidas Sneakers

Any outfit could be paired with a classic pair of Adidas sneakers, featuring the unique 3-line design on each side of the shoes.

Currently, these sneakers have come back as a very popular trend, that has lasted since it began in late 2015. You can buy the uber cool a modern Adidas version here

White or black sneakers are a timeless wardrobe piece that you can never go wrong with. They can be paired with jeans and a t-shirt, but also with a blazer and dress pants for a modern, edgy look.

Every man should own at least one pair of simple white or black sneakers, outside of the pair they use to workout. During his early years as a star, Leonardo DiCaprio was often seen sporting different versions of the classic Adidas sneakers

Read: Battle of the Legendary Sports Brands: Adidas vs. Puma

Shoes Within Hip-Hop Subculture

Hip-hop shared the stage with grunge music during the 90s, as another genre that became massively popular.

The people who listened to hip-hop formed a subculture group linked to the music they enjoyed, the way they lived their lives, and the distinctive way they chose to dress.

Artists like Public Enemy, Tupac Shakur, Snoop Dog, Ice Cube, and Jay Z dominated the decade during hip-hop’s golden era. 

The footwear of choice among this subculture could vary but was centered around a street style aesthetic. Oversized gold chains, baggy pants, and baseball caps were prominent. 

Nike Sneakers

In terms of shoes, Nike was the brand that ruled the hip-hop scene. Ice Cube was never seen without a pair—they became iconic of the subculture and music genre in general. All the most famous rappers sported them and promoted them.

Hip-hop became more than a subculture during the 90s—it developed into its trend that many other subcultures followed such as nu-metal.

Nike is one of the bestselling shoe brands in the world and is still famous for the classic high-top sneakers that boomed during the 90s. Newer versions can be purchased here

And if you could splurge on any of these iconic models from the brand, you were in luck!

Nike Air Huarache

This model came out in 1991 and was considered to be a very exclusive design. It was a running shoe with a neoprene upper that resembled a sock. It was designed by Tinker Hatfield and it was marketed as a “hug on your foot”.

Nike Air Zoom Spiridon

This was one of the first models that featured Zoom Air cushioning in the sole. It was launched in 1997 and had a bunch of unique features like the thick design lines and the large Swoosh. Aesthetically it contrasted materials and colors for a striking design. The logo also has a metallic look that shines in the light. Pretty cool, right?

Nike Air More Uptempo

This basketball shoe was released in 1996 as a basketball shoe. They were also very in with the hip-hop crowd. Their main feature was the large AIR lettering on the side of the sneakers that matched the color play of the sole. 

High top sneakers

During the 90s, most high-tops were either Converse or Vans and looked pretty much the same, with a huge percentage of models being all-white or red (especially for Chucks!). However, other brands offered a bulkier, padded look for high-tops that became strikingly popular and a staple of the decade. These types of high-tops had more in common with the “Back to the Future” model than the original basketball court high-tops created by Chuck Taylor.  

In case you are wondering, high-tops share all of the features of a low-top (rubber non-skid outer sole, canvas/leather upper, and lace-up front) but are characterized by one difference: they extend over the wearer’s ankle to varying degrees. They are usually considered athletic shoes and used in basketball and other court sports. 

The most important variations for high-tops when it comes to design happen in regards to the way they hold on to the feet. Meaning, if they are either laced up or slip-on. 

The slip-on variation is rare and considered more of an aesthetic feature for shoes that won’t be used athletically. Usually, they focus on big tongues and have elastic on the inside of the shoe that provide the necessary closure over the foot. Sometimes they also add velcro closure outside, on the sides of the tongue, for added tightness. 

Typical brands renowned in the 90s for their high tops were Converse, Vans, Nike, Reebok, and Fila. However, nowadays most famous brands of sneakers carry at least a few high-tops models because of how popular and in-demand they are!

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