Top shoe recommendations to help you take on the day with confidence and style.

Growing up as a kid in the ’90s, I had two heroes: Michael Jordan and Benny “The Jet” Rodriguez. MJ, the greatest basketball player of all time (don’t @ me); and Benny the Jet, the fictitious character from The Sandlot who hopped Old Man Myrtle’s fence and “pickled the Beast” in order to get back a ball signed by Babe Ruth, were larger than life. They were demi-gods endowed with superhuman abilities, and they were endlessly cool. And, in my mind, they both derived their powers from the same source: their shoes.

Jordan wore his signature sneakers which are, nearly two decades since MJ retired from basketball, arguably the most iconic shoes on the planet. I remember watching Space Jam and desperately wanting the Jordan 11s he wore (spoiler: It’s been 23 years and I still desperately want them). Benny wore PF Flyers; “Shoes guaranteed to make a kid run faster and jump higher,” says the film’s narrator. And I believed it. After all, they were the “secret weapon” he used to face The Beast, something only one kid in history had ever attempted … and he got eaten.

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Chase’s Pick: New Balance 997H V1

Finish Line – Lakeland Square Mall

Price range: $$

“I’ve liked New Balance since I was back in high school. They’re another go-to that can be worn with anything. I consider them the high-class athletic shoe. And there’s a reason dads love to wear New Balance: they’re very comfortable! The 997Hs are hip, rare, and this colorway is outstanding.”

Joe’s Pick: Adidas Originals NMD R1

Champs Sports or Finish Line – Lakeland Square Mall

Price Range: $$-$$$

“I’m a huge fan of Adidas’ athletic shoes. The Ultra Boosts are a bit more pricey and harder to come by; whereas the NMDs are more affordable and come in a greater variety of colorways, which allows for you to more easily differentiate your look from what everyone else is wearing.”

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Chase’s Pick: Nike Air Force 1 Low

Champs Sports – Lakeland Square Mall

Price Range: $-$$

“These Nike classics are simple, well known, and comfortable, too. Today, the oversized/Dad shoe is very fashionable. Great for Florida, the AF1 can be worn with shorts or jeans. The white-on-white colorway allows you to match any outfit and still look classy while doing so.”

Joe’s Pick: Reebok Workout Plus

Champs Sports or Finish Line – Lakeland Square Mall

Price Range: $$

“This is a nostalgia pick for me because Reeboks were insanely popular at my middle school in the mid-2000s for girls and guys, and I’m thrilled to see the Workout and Classic Reeboks making a comeback. Classic shoes always come back around. The “gum bottom” look on these kicks is a nice flourish 12-year-old Joe didn’t have on his, so now I definitely want to go back in time and bless myself with these.”

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Chase’s Pick: Jordan Retro 1 OG

Jimmy Jazz – Lakeland Square Mall

Price Range: $$-$$$

“From the time of their release in 1985, the Jordan 1s have never taken a break. These shoes are trending lately and will forever be a staple in the sneaker world. The hi-top look allows you to wear them with chinos, rolled up denim from the local 5th & Hall, or paired with custom mid-calf socks from Oldskoolwear.”

Joe’s Pick: Puma RS-X

Champs Sports or Finish Line – Lakeland Square Mall

Price Range: $$-$$$

“I had two pairs of Pumas way back when, but I can guarantee they didn’t have the kind of heat as the Puma RS-X. Considering Rihanna and Jay-Z’s involvement with the brand over recent years and their splashy push back into the basketball-shoe game, expect Pumas to be the shoe your friends are jumping on six months from now.”


Today, if I’m honest, I still think of shoes as “secret weapons.” Whether you’re lacing them up, slipping them on, or buckling them up, shoes have this ability to shift — quite literally — how we walk and talk and feel. Having the right pair is essential, particularly for a kid walking into a new school year. So I asked my good friend and avid sneakerhead Chase Cheek to help me create a list of some of our top picks for shoes this school year. We’ve decided to break up our picks into three categories in order to help you find the best shoe for your style. The categories are: Classic, Athletic, and Trendy.

Chase, before we get started, tell me a little bit about what you look for when you’re choosing a new pair of kicks to add to your collection.

Chase Cheek: Personally, it’s about the occasion. What am I buying these shoes for? It could be a day at school, a trip to the gym, or the classic “date night.” Understanding the occasion is crucial. I think it’s key to “dress for the occasion,” and this applies to the shoe choice as well. I think shoes can make or break a great outfit.

Joe Hepler: I couldn’t agree more, Chase. Shoes are the centerpiece of any outfit, particularly when that outfit might be a drab school uniform. So let’s jump into the categories and share our picks for our favorite shoes going into this new school year.