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Oakley Software is Making a Comeback – Here’s Why

Once known for its bold, futuristic style, Oakley’s vintage clothing has resurfaced across resale markets, reigniting interest in the brand’s forgotten fashion era. After years of fading from the style spotlight, Oakley now seems poised for a revival—but where is it taking this comeback?

A big Oakley logo with a background of Oakley t-shirts and Oakley long sleeves.
Image by Jessica Segarra/Trill

Recently, there has been a huge resurgence of Oakley clothing from the 90s and early 2000s in the vintage and resale markets. Oakley garments, such as hoodies, t-shirts, and crew-neck sweatshirts, have become highly sought after and come with a hefty price tag.

But why the huge comeback from a brand that was deemed as unfashionable and stale?

A brief history of Oakley

In 1975, Jim Jannard founded Oakley in southern California in his garage. At first, Oakley specialized in bike grips for motocross, which eventually led Jannard to create goggles for motocross in 1980. In 1984, Oakley released its first sunglasses, the “Factory Pilot Eyeshades.” Through the 1980s, Oakley continued to make new eyewear with models like the “Frog Skins” and started further solidifying itself as an iconic fashion statement.

By the early ’90s, Oakley had moved into the “Mad Scientist” era of their brand, which was defined by the futuristic look that many still associate with Oakley. During this decade, professional athletes like Michael Jordan and Denis Rodman were seen wearing Oakley eyewear, firmly launching the brand into the mainstream.

This fashion momentum carried over into the turn of the century. Oakley eyewear appeared in blockbuster movies like Mission: Impossible 2, Fight Club, and Blade.

During this time, Oakley was looking to further promote its status as a unique, fashion-forward brand, looking to make cutting-edge products that had never been seen before.

With this agenda came the release of the “Over-the-Top” sunglasses first seen in the 2000 Olympics in Sydney, Australia.

Items like the “Over-the-Top” glasses elevated Oakley beyond just an eyewear brand.

Through the rest of the early 2000s, Oakley continued to make innovative products, staying true to its mission to be cutting-edge.

That was until 2007, when Oakley was sold to Luxottica for $2 billion. While this increased their global reach, drove more sales, and solidified Oakley into a household name, it also started the decline of Oakley’s originality and innovation.

So, where does Oakley Software fit in this puzzle?

Oakley software

Oakey began making clothes in the early 2000s as an effort to expand beyond eyewear. They started making t-shirts, hoodies, hats, and other garments. This new division of Oakley reflected the brand and culture surrounding sportswear at the time.

Other sports brands like Nike made similar clothing during this time. Both Oakley and Nike blended tech and sports, a token of the sportswear industry in the early 2000s.
This mixture of tech and sports during this time intrigues me and stands out from any other period of fashion, and Oakley arguably takes the cake when it comes to this forgotten style.

Oakley carried its originality from the “Mad Scientist” era into its early clothing designs. It often showcased the Oakley logo in a metallic graphic “Ellipse” or other enticing graphics.

Oakley had done a fantastic job translating its cutting-edge designs into their clothing. Oakley software was just as innovative as its eyewear, and the market reacted well in the 2000s.

But after Oakley’s sale to Luxottica, this era of clothing faded away.

What happened to Oakley software?

After the sale, Oakley simplified its clothing designs to cater to a broader customer base. The brand abandoned its original designs and introduced more lifestyle-oriented and minimal styles.

It was not just Oakley that fell victim to this; other sportswear brands also became more minimal moving into the 2010s. The blend of tech and sports that was seen across the industry during the late 90s and early 2000s was forgotten and replaced by logo-driven basic designs.

A black Oakley t-shirt on a model that reads: Oakley, Established 1975
A modern design– Oakley SI Indoc Tee (Credits: Oakley)

However, in recent years, there has been a huge resurgence of the Y2K style. This resurgence did not just stop at brands like Affliction and Tapout. The style draws some inspiration from the 2000s sports wear scene.

And that’s where vintage Oakley comes (back) into play.

Why did vintage Oakley come back?

Vintage Oakley came back for a few reasons. The first is a market craving for vintage. Vintage clothing has remained popular for a long time, so it’s no surprise that people also seek vintage sportswear.

The second reason is that the 2000s style is undoubtedly making a comeback. Clothing from this time has recently flooded the vintage market, and fashion culture has fully embraced it. This sought-after style has expanded to include both streetwear and sportswear.

Lastly, vintage Oakley is ‘exclusive’. It is hard to find and has a high price tag compared to other vintage sportswear items, which makes it more fashionable and desirable.

Oakley Software captures a look you won’t find anywhere else, blending tech and sports in a distinct way. These elements stirred up the fashion scene’s craving for vintage Oakley.

Where does this leave modern Oakley?

Vintage Oakley’s revival did not go unnoticed by the brand. In the 2020s, Oakley brought on Kyle Ng, the co-founder of Braindead, to the Oakley Factory team. The purpose of the Oakley Factory team was to rework and release old Oakley styles in a new way. One of the first products released by the team was Oakley’s quintessential shoe, released in the early 2000s, named the Oakley “Fleshes”.

A pair of Oakley fleshes, specifically the Oakley Factory Team Flesh Sandal model
A truly unique silhouette that has become a staple: the Oakley Factory Team Flesh Sandal. (Credit: Oakley)

Oakley re-released the Flesh shoes to target the vintage Oakley market, which continues to grow rapidly.

It is good to see that Oakley is not letting their vintage-style market go unnoticed. By bringing on different creative individuals and realizing vintage styles, it is safe to say Oakley is making progress.

The Oakley Factory team is taking Oakley in the right direction. It will be extremely interesting to see what the team can produce over the next few years.

It seems that Oakley is not shy about turning around the narrative of its modern designs. One instance that shows this is their new line of “Artifacts From The Future,” a line that looks to be giving a twist on old Oakley designs in a modern manner.

Oakley's Artifacts From the Future line, with Jaylen Brown modeling sunglasses on a planetary backgorund.
Oakley Artifacts From the Future (Plantaris Sunglasses), Jaylen Brown. (Credits: Oakley)

Undoubtedly, Oakley is a fashion cornerstone. When discussing sportswear, you have to include them in the conversation. Even though many considered the brand unfashionable for years, their revival offers something you will want to witness.

But what do you think? Is the swelling of vintage Oakley in the resale market and the brand’s resurgence of vintage styles something exciting, or just another recycled trend?

Written By

I have always had a deep passion for fashion and writing, my two favorite outlets for self-expression. They give me a way to share my creativity with the world, and bring joy to myself and others.

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