All the Ways to Wear is a monthly series where we round up the personal twists the Who What Wear team is putting on one particular item, style, or trend. Whether it’s the trending denim of the moment or the season’s It print, we hope to inspire your daily outfits and up the cost per wear on some of our favorite items.
I can still remember my first pair of Sperrys. I begged my mom to get them for me for Christmas even though I lived in Northern California, where the cold temps called for footwear more along the lines of wellies and fur-lined boots (whoops). Still, I think I ended up wearing them almost every day that year. Fast-forward to today, and the preppy trend is making quite the resurgence in the fashion scene. And of course, the style set is hopping on the wave quickly with pieces like pleated miniskirts, polo shirts, and—yep, you guessed it—Sperry boat shoes. I tapped two of my editor friends, Michaela Bushkin and Sierra Mayhew, and one incredibly stylish TikToker, Dannaed Garcia, to see how they’re incorporating the shoe style into their wardrobe rotations this spring. And trust me—you’ll want to take notes. Keep scrolling to see all the ways to wear Sperry’s most iconic shoe.
“I’m so happy that preppy style is in this spring. When I was a kid, teenagers dressed preppy, but I was too young to dress up. I’m super excited to experiment with my style this season. I’ll for sure be incorporating modern preppy pieces like Sperrys into my wardrobe. Not only are they classic, neutral shoes, but I love how comfortable they are. (And when I say comfortable, I mean I can literally run a mile in them and not feel a thing.) They go with any spring look, including dresses, skirts, shorts, jeans, and even athleisurewear. They are just so versatile and so classy.”
“I’m a denim girl all year round, so I’m happy that my Sperrys looked so cute (if I do say so myself) with this wide-leg, light-wash style I’m loving at the moment. The navy shoes and blue denim work together from a color perspective, so that’s where I started. I wanted to incorporate another bright hue that would complement the navy footwear, and I landed on this green tank top and sweater (because even in L.A., weather can be unpredictable). I like the juxtaposition of the blue and green shades here. It feels so fresh for the spring season.”
“I’m excited for spring and the opportunity to finally show some skin. One of my favorite ways to do this elegantly is through footwear, so you can imagine my excitement when the boat shoe showed up at my door. The first time I wore this minidress was for a nice dinner, and I wore a pair of high heels and a mini bag with it. It’s nice how versatile it can be because as soon as I threw on the Sperry shoes, the whole look was immediately perfect for a casual weekend. (The rawhide laces and contrast stitching give off that easy, laid-back vibe.) I love dressing from the shoes up, and since these are so comfortable, there are a million places I could take this look.”