The best vintage tennis shoes are the one's that have a truly defining design characteristic. Many shoes have been well made, but if they do not have that pop about them that makes them stand out they will not become classics. Shoes are kind of analogous to cars in that the 1980's Taurus was a well-made vehicle but its not a classic like the 1960's Ford Mustang because it does not remind you of the time you lusted after it because of its side vents of ragtop.
- Nike Air Max 95. These running shoes sported the most air bubbles Nike ever included on a shoe at the time. The sides of these shoes features a slowly fading color scheme and they became popular with yuppies and urban types alike making them one of the best vintage tennis shoes ever produced.
- Nike Air Penny II. The inclusion of suede and faux-carbon fiber on these shoes foreshadowed a trend that would soon arrive in the automotive world. A 1990's shoe that acts as a stylistic precursor to 2000's automotive bling must be included on any list of the best vintage tennis shoes.
- Converse Chuck Taylor All-Stars. One of the most enduring pieces of footwear of all time is also one of the best vintage tennis shoes of all time. These shoes origins lay in the 1930's and as late as the 2000's designer John Varvatos was still making them with his own personal touch.
- Nike Air Force Ones. Nelly made a song about these signature 1980's basketball shoes at a time when throwback Jerseys were all the rage solidifying these sneakers position as one of the best vintage tennis shoes.
- Reebok Pump. The cultural impact of these shoes can not be understated. Firmly seated in 1990's excess and one of the best vintage tennis shoes, these Reebok's featured an inflatable pad in the tongue for the ultimate in customization to one's foot. The orange basketball at the top of the tongue was a design feature that is one of the most memorable in shoe history.
- Nike Air Jordan. Each season would bring a different iteration of the Jumpman branded shoes that are on the top of anyone's list of best vintage tennis shoes. The styling of these shoes changed drastically from year to year with each generation being held in high regard amongst vintage shoe connoisseurs of varying tastes.
- Bally Animal. The Swiss dress shoe maker, Bally, crafted one of the best vintage tennis shoes of all time when they manufactured the Bally Animal. These shoes featured a train of walking animals etched into the side of the shoe's sole creating a design like no one in the sneaker industry had seen before. The impact of these early 1990's shoes upon New Orleans rappers was so huge that even in the late 2000's they were being name dropped by Lil' Wayne.
- Nike Air Shake. These shoes would become one of the best vintage tennis shoes ever sold due to their unique design that features a flap covering the laces and an embroidered basketball rim on the rear of the shoe. Oh, did I mention these were also popularized by Dennis Rodman at the height of his popularity? These shoes styling was about as outlandish as his hair color making them an instant classic.
- LA Gear Lights. During the early 1990's people felt the need to have blinking lights on their shoes. Such an unnecessary design trait made these sneakers a shoe-in for best vintage tennis shoe hall of fame.
- K Swiss. Sometimes a fashion item becomes a classic due to its simplicity and that is why the 1980's K Swiss sneaker is included in the list of best vintage tennis shoes. There were no gimmicks with these sneakers; no blinking lights, no air bubbles, no pneumatic devices of dubious utility. Nope, these shoes were just white with sewn on white leather stripes. Keep them clean and you will look clean. Such a clean, classic look will have you telling your friends to do what they do, but watch your shoes.
What Others Are Reading Right Now.
How to Turn (Almost) Every Lady’s Head
Top female stylists share their favorite men’s looks.
10 Kung Fu Movies Every Man Should See
From the absolute classics to the so-bad-they're-amazing.
10 Red Flags That Kill Your Chances With Women
Wondering why that first date didn’t lead to a second? Read on.