What To Look For In A Pair Of 'Cool-Girl Sneakers,' According To A Sneakerhead

Here are some sneakerhead-backed tips for investing in a pair of trendy sneakers.
Many sneaker-lovers have impressive collections that fill entire closets.
Edward Berthelot via Getty Images
Many sneaker-lovers have impressive collections that fill entire closets.

For most people, buying sneakers used to be about choosing a functional shoe for running, hiking or other forms of exercise. But anyone who’s paid attention to style trends in recent years knows that sneaker culture today is about so much more than that.

Instagram is full of accounts from serious “sneakerheads” showing off their impressive collections of limited-edition shoes from brands like Nike, Adidas and more. Streetwear trendsetters have ushered in an era of “ugly sneakers” (much to the delight of supportive shoe-loving podiatrists) and what many have branded “cool-girl sneakers.” Celebrities like Cardi B, Gigi Hadid and Selena Gomez are releasing their own special lines of sneakers or signing on to be the faces of brands like Puma and Reebok.

On Inauguration Day, President Joe Biden’s granddaughter Maisy sported a pair of Nike Air Jordan 1 Mid “Sisterhood” sneakers before changing into another pair of Nikes for the evening events. Meena Harris’ husband Nikolas Ajagu also wore Air Jordans that day, the Air Jordan 1 Retro High Dior, which originally retailed for $2,200.

The global sneaker market is growing. And by some estimates, investing in certain sneakers could lead to better returns than investing in gold. So while serious sneaker fandom can date back to Michael Jordan’s early Nike days in the ’80s (or perhaps even earlier), there’s no denying that what was once a relatively niche subculture has reached mainstream status.

“The number of pairs you have should not define whether or not you belong in the sneaker community.”

- Alyssa Ong, sneaker fanatic behind the Instagram account @sneakerlei

That doesn’t mean everyone has the budget to build a fancy sneaker collection, however. For many, the goal is simply to buy a nice pair of shoes that will make them feel stylish as they hit the streets.

But investing in a pair of trendy sneakers for personal use can feel like a daunting endeavor for novices. Many trendy options aren’t exactly cheap, and it’s hard to know which pair will give you the most bang for your buck.

To help guide new enthusiasts, HuffPost asked Alyssa Ong, the sneaker fanatic behind the Instagram account @sneakerlei, to share her advice for buying a pair of fancy kicks. Read on for her four biggest tips.

Make sure they’re comfortable.

“One very crucial quality I look for in a shoe is comfort,” Ong told HuffPost. “It is important for me that my special sneakers should not only look aesthetically great, but it should also feel good wearing and walking in them.”

Look no further than than “Friends” episode, “The One with Monica’s Boots,” to understand the pitfalls of spending a lot of money on an uncomfortable pair of shoes. Serious sneakerheads may shell out thousands on shoes that will mostly sit on shelves, but a novice should get more wear out of their investment, especially since sneakers are traditionally thought of as walking shoes.

“Honestly, nothing ruins a special pair more than a sneaker that makes you feel like you’re literally walking on sandpaper and leaves your toes and feet all cramped up,” Ong said. “I’ve personally had some very special sneakers in the past that are absolutely uncomfortable. It ruins the experience and those pairs have been kept on the shelf ever since.”

Don’t buy a pair you don’t love just because it’s trendy.

Sneakerhead culture is all about keeping up with the latest trends and finding rare, limited edition shoes to invest in. But that doesn’t mean you should only look to the trends or the most exclusive sneakers you can access when picking an expensive pair to buy. Instead, opt for shoes that you’re excited to wear and will make you feel good.

“When it comes to this, you’ve got to ask yourself if you personally love the shoe or you’re getting it simply because everyone you see on social media has it,” Ong said. “Since hyped sneakers follow a trend, the trend is constantly changing. Splurging on a pair with a high resale value simply because you feel pressured to have it in your collection will leave you relatively disappointed once the trend dies. Always invest in a pair that you’ll love irregardless of the trend and time.”

Cesar Vasquez, who owns 300 pairs of limited-edition sneakers, is photographed at his Los Angeles home with some of them. He often camps outside sneaker boutiques to get rare shoes, which he then resells on eBay for triple the price.
Photo by Annie Wells/Los Angeles Times via Getty Images
Cesar Vasquez, who owns 300 pairs of limited-edition sneakers, is photographed at his Los Angeles home with some of them. He often camps outside sneaker boutiques to get rare shoes, which he then resells on eBay for triple the price.

Pick a versatile shoe.

Anyone interested in streetwear knows that sneakers aren’t just meant for playing sports or pairing with athleisure (even if that’s basically been our entire wardrobe in the pandemic era). In recent years, people have been wearing sneakers with dresses, tuxedos and even their work clothes (and not just in a “Working Girl” sense).

With that in mind, it makes sense to consider a pair that you can envision wearing in a variety of contexts to maximize your use.

“Ultimately, when choosing a pair of sneakers, you would want to choose a pair that is comfortable yet versatile ― one that you will be able to wear on various occasions with different outfits,” Ong said.

Don’t get caught up with quantity.

All those Instagram posts from sneaker collectors showing off their racks of hundreds of shoes may feel tantalizing, but it’s vital to be mindful of your actual budget.

“To all those who are new or getting into the sneaker community, remember, you do not need to purchase every new pair that is released,” Ong said. “It is very important to stick to what is within your means. Do not get caught up with everything you see or hear on social media. The number of pairs you have should not define whether or not you belong in the sneaker community.”

She emphasized the value of creativity and self-expression over big budgets in the world of sneakers.

“You can be creative with the pairs that you currently have,” Ong noted. “Be true to your own style and sense of self, while inspiring others to do the same. At the end of the day, it is more important to stick to what you truly love and are passionate about.”

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