1. Air Jordan 12 OVO (Drake Edition)
   Air Jordan 4 Eminem
2. Nike Air Max 1
   Nike Air Jordan X "City Series"

Nike's technologically advanced air cushioning system has been around since the '80s, but the Nike Air Max 1 was the first sneaker that featured a famous "air" window. Their unique technology might be a few decades old, but Nike Air sneakers look super cool even today.

1. Adidas Trimm Trab
   Air Jordan III OG
2. Nike Foamposite One "Sole Collector"
   Air Jordan 12 (Flu Game)

Stripped favorites of '80s UK football fans, Adidas Trimm Trab are still instantly recognizable. But it's almost impossible to find a mint vintage pair today, because the soles on the original models famously deteriorated over time, even new ones.

1. Onitsuka Tiger Corsair
   Nike Dunk Low Pro SB Pigeon
2. Vans Half Cab Pro
   Vans Era Checkerboard

Onitsuka, an old shoe company from Japan, has made brand sneakers since the late 1940s. Its best-selling Onitsuka Tiger had a big influence on the development of sneaker technology and design in the first part of the 20th century.

1. Nike Cortez
   Vans Checkerboard Slip-On
2. Vans Old School Pro Vans
   Converse All Star

A legendary shoe with classic design didn't change since its first release in 1916. Converse All Stars (or 'Chuck Ts') are still a big hit amongst students, skaters, indie kids, punks, and adults who prefer classic, timeless designs.

1. Air Jordan 12 OVO
   Nike Lebron 9 Low "LeBronold Palmer"
2. Air Jordan VI (1992 Olympics)
   Adidas Superstar

Adidas Superstar holds the title of a design sneaker icon since the late '60s. These collectible sneakers also had a massive impact on many musical trends, cultures, ads, and tribes.

1. Nike Air Jordan 1
   Nike Yeezy 2 Red October
2. Air Jordan XX1 SE "SLAM 100"
   Vans Golf Shoe

In the '80s, these shoes were banned by the NBA in the US because they were breaking its color rules. However, banning made them even more popular in America, inspiring a never-ending line of follow-ups.

1. Nike Air Jordan II
   Etnies Fader
2. Air Jordan 5 Oregon Ducks
   Air Jordan 10 PSNY

Etnies Faders are well known for classic, appealing aesthetic, contrasting colors, and solid sturdy construction. While not everyone can call them iconic, the original sneakers from California aren't cheap.

1. Nike Dunk Low Pro SB Freddy Krueger Sample
   Adidas Samba
2. Nike Bruin
   Nike Air Jordan III

Nike Air Jordan III was the first sneaker to feature the now iconic Jumpman logo and the air sole window units.These legendary sneakers are popular to this day! A retro pair can cost up to $800!

1. Adidas Samba
   Nike Air Jordan 1 KO
2. Nike Air Jordan VII "Olympics"
   Air Jordan III "Oregon Ducks"

Iconic black-and-white sneakers, Adidas Samba are still among Adidas' bestsellers. The old-school classic, first released in 1950, set a high standard for all sneakers to follow.

1. Adidas Kegler Super
   Nike Bruin
2. Eminem Air Jordan IV
   Nike Air Jordan III

Nike Bruin is, quite simply, a legendary sneaker that has been around since 1972. A low-top basketball shoe with a large white Nike swoosh, as well as a matching white sole, helped launch the Nike brand in the 20th century.

1. Adidas Kegler Super
   Vans Era Decon CA
2. Air Jordan 10 PSNY
   Puma State

These sneakers serve as the great example of a timeless piece of classic design. Puma State (also known as Suedes in the US) have a long history and are still popular today, especially among hip-hop singers, dancers, skaters, basketball players, and street casuals.

1. Adidas Stan Smith
   Vans Authentic
2. UNDFTD Air Jordan IV
   Nike Air Jordan III

Originally designed as tennis shoes, the Adidas Stan Smith sneaker was released in 1965. Endorsed by iconic US tennis player Stan Smith, these bad-boys are simply legendary. They were so popular, that in 2014, they were treated to a re-release.

1. Nike Air Max 95
   Adidas Gazelle
2. Vans Authentic Platform
   Adidas TRX Comp

The TRX range is a line of running shoes released by Adidas in the '70s. However, those sneakers looked so good that they were quickly adopted by fashionistas. By the way, the most loyal fan of these Adidas sneakers was Bob Marley, who was often seen sporting a pair of TRXs!

1. Air Jordan IV Motorsports
   Nike Air Jordan III
2. Vans Checkerboard Slip-On
   Adidas TRX Comp

Although Michael Jordan had to stop riding motorcycles when he began his NBA career, his passion for motorsports never went away, inspiring this iconic pair. These Jordans were so popular in the previous century that in 2004, the company decided to release them again.

1. Air Jordan 5 Oregon Ducks
   Adidas Gazelle
2. Nike Air Force 1
   Nike Dunk Low Pro SB Freddy Krueger Sample

The same way that the Samba became a staple of shoe wardrobes, so the same can be said of the Gazelle. Adidas' classic training shoe, out in 1968, has been available in pretty much every possible color scheme over the years.

1. Converse All Star
   Adidas Trimm Trab
2. Vans Old Skool
   Nike Air Jordan 11

When Michael Jordan decided to patent leather on a sneaker, Nike listened and released this iconic pair. The Nike Air Jordan 11 is still regarded as the most beloved and unique silhouette of all.

1. Nike Air Max 1
   Nike Yeezy 2 Red October
2. Vans Era Checkerboard
   Nike Air Jordan 1

Self-respecting '70s skateboarders were buying only sneakers made by Vans and this trend is still alive today. Plain California deck shoes would not have attained their status without the skaters who were actively promoting these shoes. The company has also involved skaters in the design of the 95, popularly known as the Vans Era.

1. Nike Air Max 95
   Vans Serio
2. Onitsuka Tiger Corsair
   Vans Carver

Nike had already had success with Air Max versions 1-3 before releasing the iconic Nike Air Max 95. The release date of these shoes mark a major leap for sneaker design that was only evolving since then.

1. Puma State
   Adidas Kegler Super
2. Vans Sk8-Hi Lite
   Adidas Superstar

These ’80s-originated classic sneakers feature the signature peg cushioning system that allows the wearer to alter the feel of the sneakers. Both waterproof and breathable, Adidas Kegler Super are perfect for any season.

1. Air Jordan VI
   Gucci Ace Low-Top Flames
2. Maison Margiela Coated Knit Sneakers
   Nike Cortez

Not everyone knows it but Nike's first-ever sneakers were actually inspired by the Onitsuka Tiger Cortez, also designed by Nike's co-founders. They were so popular, that Nike released these sneakers in pretty much every imaginable color scheme and material.

1. Gosha Rubchinskiy x Fila
   Air Jordan V Bin 23
2. Braindead x Vans
   Common Projects Blush Achilles Low

A pair of shoes that cost at least $1,500 online, the Air Jordan V Bin 23 is made of metallic, reflective material. The re-released pair pay homage to MJ's style when he was playing against the Milwaukee Bucks in the 1990 NBA Playoff.

1. Nike Air Force 1
   Reebok x Vetements Instapump Fury
2. White Mountaineering x adidas NMD Trail
   Buscemi 110MM Black/White/Red

Released in 1982, the iconic and collectible basketball shoe with Nike's unique air cushioning system was extremely popular among basketball players. For a few years, it was strictly a basketball shoe but in the late '80s, Nike Air Force 1 also became a trendy fashion item.

1. COMME des GARÇONS x NikeLab VaporMax
   Rick Owens x adidas Walrus
2. Balenciaga Speed Trainer
   Nike Foamposite One "Sole Collector"

Nike Foamposite One "Sole Collector" is one of the most recognized sneakers of all-time thanks to its unbelievable design and unusual color. Originally released in 1997, they were created for basketball players and debuted Nike's famous Foamposite technology.

1. Valentino Camustars Rockrunner
   Saint Laurent SL/06
2. Air Jordan XX3 Titanium
   Supreme x Louis Vuitton Sneakers

Air Jordan XX3 Titanium were a limited release, with only 1,058 pairs being released around the world. Their original retail price was around $200 but since not everyone could buy them, the price skyrocketed pretty quickly!

1. Nike Lebron 1
   Fear of God Military High-Top
2. Raf Simons x adidas Ozweego 2
   Lanvin Vulcanized Canvas

Since 2003, all eyes have been on LeBron James who made the Cleveland Cavaliers and Cleveland itself famous again. James’ signature Nikes change drastically every year, but always feature the unique design and the most coveted colorways in the culture.

1. Undercover x Vans Era
   Nike Yeezy 2 Red October
2. Aime Leon Dore Q44
   Off-White x Nike Air Force 1

Shoes that cost thousands of dollars even in Walmart (the famous budget chain store had a few pairs on sale for $6,499!), Kanye West's Red October is an extremely rare and desirable pair of sneakers.

1. Common Projects Blush Achilles Low
   Nike Dunk Low Pro SB Paris
2. Air Jordan V
   Jordan’s XXXI Gold

Not long ago, Jordan Brand surprised its fans with the release of a special edition Air Jordan XXXI. The sneakers were available in limited numbers in New Orleans only, and are easily recognisable thanks to their bold metallic gold finish.

1. Fear of God Military High-Top
   Nike Dunk Low Pro SB Pigeon
2. Eminem Air Jordan IV
   Etnies Fader

Probably the most hyped sneakers ever, the Nike Dunk Low Pro SB Pigeon features two contrasting colors - grey suede and bright orange - as well as an embroidered pigeon on the heel that represents NYC.

1. Vans Half Cab Pro
   Adidas Samba
2. Puma State
   Air Jordan III OG

These Jordans are completed with classic Nike Air branding at the heel and outsole and a classic fire red tongue lining, a design element you won't often see.

1. Air Jordan 5 Oregon Ducks
   Nike Air Mag Back to the Future
2. Gucci Ace Low-Top Flames
   Air Jordan 4 Undefeated

The Ducks-flavored Jordan line has a few notable pairs, including the Air Jordan 5 “Oregon Ducks” released in 2013. The bright green pair with the face of mascot Puddles on the back end and an “O” logo attached on the tongue is arguably the best Oregon Ducks-themed pair of shoes.

1. Maison Margiela Coated Knit Sneakers
   Air Jordan 12 OVO
2. Eminem Air Jordan IV
   Adidas Superstar

These trendy sneakers made of premium leather feature textured overlays and the historic silhouette designed by Tinker Hatfield. In case you didn't know it already, OVO means “October's Very Own” - it is the name of Drake's record label and clothing line.

1. Adidas Stan Smith
   Air Jordan 4 Eminem x Carhartt
2. Nike Air Jordan 1 Low
   Nike Dunk Low Pro SB Freddy Krueger Sample

Here is a rare and extremely hot shoe with the colorful spots of blood. Freddy Krueger would be definitely proud to see a pair of sneakers devoted exclusively to him.

1. Vans Checkerboard Slip-On
   Vans Golf Shoe
2. Onitsuka Tiger Corsair
   Air Jordan 10 PSNY

A real sneaker collector would love to add a pair of Public School x Air Jordan 10's to his or her collection. Air Jordan 10 PSNY are crafted with premium leather, feature black detailing, and PSNY branding.

1. Reebok x Vetements Instapump Fury
   Air Jordan V
2. Braindead x Vans
   Nike Air Jordan 1

The Air Jordan IV started the flight theme when it spelled out "Flight" across its tongue. The Air Jordan V took it to next level by featuring a unique design inspired by WWII fighter planes.

1. Adidas Trimm Trab
   Nike Yeezy 2 Red October
2. Nike Dunk High Pro SB "T-19"
   Converse All Star

In the world of sneakers, Nike Dunk High Pro SB "T-19" holds a special place. A lot has happened in the kicks game since the first Nikes were released! This pair, released in Tokyo, marks the return of modern high-tech sneakers as trendy streetwear.

1. LX Van Doren Winnie the Pooh
   Nike Air Max 1
2. Adidas Superstar
   White Mountaineering x adidas NMD Trail

Authentic Vans with a goofy yellow bear are hard to find. You'll be extremely lucky to find a decent pair for a fair price on Ebay!

1. Vans x Disney Classic Slip-On
   Nike Air Mag Back to the Future
2. Vans x Pendleton x Nibwaakaawin Classic Slip-On
   COMME des GARÇONS x NikeLab VaporMax

This shoe replicates the well-known shoe worn by Marty McFly in "Back to the Future II." The futuristic shoe features a lot of cool details like glowing LED panels, upper contours, and luminescent Nike logo. By the way, the sneakers can glow up to 5 hours from the built-in battery!

1. Adidas Samba
   Etnies Fader
2. Nike Air Force 1
   Air Jordan 4 Undefeated

The Air Jordan 4 Undefeated is among the most rare and coveted Air Jordan retro releases ever! Moreover, these best-selling sneakers, out in 2005, became the first-ever Jordan Brand collaboration with a third party in history!

1. Beatles Sk8-Hi Reissue Vans
   Nike Air Jordan 11
2. Rick Owens x adidas Walrus
   Adidas TRX Comp

Inspired by the iconic English rock band and the graphics from their legendary album and film, The Vans x Beatles Yellow Submarine signature Sk8-Hi Reissue is a real masterpiece!

1. Vans Syndicate x Wtaps Bones Era
   Saint Laurent SL/06
2. Vans x Robert Crumb
   Nike Air Max 95

Vans might be cheap and easy to find, but thanks to its wide swath of limited editions and collaborations, there are some rare gems like Vans Syndicate x Wtaps Bones Era that cost thousands of dollars!

1. Air Jordan 5 Oregon Ducks
   Nike Dunk Low Pro SB Freddy Krueger Sample
2. Balenciaga Speed Trainer
   Vans Classic Star Wars Slip-On

Not a long time ago in a galaxy far, far away Vans created unique sneakers for the devoted fans of the epic space opera. Vans x Star Wars collection features artwork from the original "Star Wars" trilogy mixed with classic Vans designs.

1. Valentino Camustars Rockrunner
   Air Jordan 4 Eminem x Carhartt
2. Vault by Vans Classic Slip-On
   Supreme x Louis Vuitton Sneakers

Consider yourself a professional collector if you have this holy grail of Air Jordan 4 releases. The exclusive, limited edition from Eminem and Carhartt features a black twill upper with hockey mask and letter “E” on each heel!

1. Fear of God Military High-Top
   Raf Simons x adidas Ozweego 2
2. Lanvin Vulcanized Canvas
   Vans Authentic

As you can imagine, it's not that easy to find the first sneaker ever released by skate shoe company, Vans. These sneakers made their debut in 1966 and were re-released countless times. However, the original shoes from the '90s are real gems!

1. Undercover x Vans Era
   Aime Leon Dore Q44
2. Air Jordan 11 Blackout
   Off-White x Nike Air Force 1

The Air Jordan 11 Blackout is a unique sneaker simply because it was never officially released. When the photos of new Jordans flooded the Internet, many sneakerheads started to believe that the sneaker would be purchasable. However, the Air Jordan 11 Blackout was only available as a sample pair and only a few people could buy a pair for $12,000!

1. Adidas Gazelle
   Puma Suede
2. Nike Air Jordan III
   Adidas Kegler Super

Puma Suede, also known as Clyde, became famous thanks to basketball legend Walter “Clyde” Frazier of the New York Knicks. In the '70s, he asked Puma to make him a wider version of their popular basketball shoe and that's how these sneakers were created.

1. Nike Bruin
   Air Jordan 10 PSNY
2. Nike Cortez
   Air Jordan 4 Eminem

This line of trendy sneakers inspired by a famous rapper is blooming. A release of the "Encore" Jordan 4 celebrates Eminem's album of the same name.

1. Air Jordan 2 OG
   Vans Half Cab Pro
2. Air Jordan 4 Eminem
   Air Jordan 12 OVO (Drake Edition)

Half Cab Pro is Steve Caballero's signature line of shoes that features both vintage design and an enhanced performance. The iconic sneakers are well known for suede and canvas details, single-wrap foxing tape, unique UltraCush HD technology, and more.