Sneakers have always been important to me. My dad had me laced in cool kicks before I was able to walk, and buying sneakers was something we bonded over ever since.
Over the years, I’ve sampled many a silhouette, not to mention a plentiful number of brands. It’s taken some trial and error to hone in on what styles and shapes complement each other best — i.e., workwear pants and Vans. Granted, my favorite pairings are subject to change with time; people used to make memes about people wearing cool trainers with bootcut jeans, but I felt no shame wearing this outfit a few months ago.
Keeping up with the “kick game” can be complicated (and in some circumstances, expensive), but also a lot of fun once you find your ideal apparel-sneaker equation. Continue below to see how I recommend styling six classic sneaker silhouettes.
1. Low-Top Sneakers
Wearing crisp new trainers with dresses makes me feel like I’ve cracked the code on creating my ideal balance, which is two parts grown woman and one part little brother — exhibits A, B, and C. If you’re wearing a bright or printed dress, I recommend pairing it with a solid sneaker, and vice versa.
2. Basketball Sneakers
Prior to this shoot, I’ve never worn a pair of Jordans off the court — I’ll spare you the details of my completely embarrassing career as a near six-foot-tall woman who stinks at basketball. Anyway, since I’m a newbie to this sneaker silhouette, I took a hint from Aleali May and leaned completely into a streetwear vibe for styling. Pairing an oversized jersey with baggy cargos brought me right to the intersection of Low-key Lane and Cool Girl Avenue, which I plan on revisiting again soon.
3. Dad Sneakers
Something about wearing dad sneakers makes me feel a lot like a seasoned professional commuting to the office — hence the blazer. After reading Leandra’s thoughts on ugly sneakers, the concept of chunky kicks as “leg weights” stuck with me. That said, going really top-heavy clothing-wise felt right because the thickness of these sneakers balanced me out on the bottom.
4. High-Top Sneakers
Although I haven’t been drawn to them in recent years, I’ll always have a soft spot for Converse. In middle school, picking out the right pair was essential to establishing my sense of self. Plus, they’re extra sentimental because my dad used to wear them as a kid back in the ’70s (often with super short shorts, I might add). So I figured, what better way to style a timeless sneaker than with some other equally timeless pieces: a white T-shirt, a rugby shirt and Dickies.
5. Minimalist Sneakers
Although I don’t naturally gravitate toward such simple sneakers, I appreciate their ability to transcend the streetwear aesthetic. With an outfit like this, I would normally reach for a strappy sandal or a mule, but these Common Projects sneakers turned out to be a seamless, no-pedicure-necessary substitute.
6. Skate Sneakers
You’d think that after being teased by a 12-year-old boy for wearing a Thrasher T-shirt, I’d learn to stop inserting myself into skate culture, but here I am. This look was born out of my appreciation for sartorial contrast: These “Old Skool” Vans are totally worthy of “shredding the gnar,” but this delicate silk skirt made me think twice about taking a seat on the subway. In my opinion, I’ve turned the “poser” nickname into a glass-half-full situation and I invite you to do the same.
So, have I successfully converted all of you into sneakerheads? Let’s chat in the comments.
Photos by Edith Young.