If you usually reach for sneakers, Sperry’s Modern Preppy Collection might give you a reason to switch things up.
I’m not the most confident when it comes to styling shoes. Most days, I stick to neutral sneakers or my trusty Chucks because I already know what goes with them. Jeans, a shirt, done.
Sperry isn’t always a brand I gravitate toward for that reason. I like the boat shoes, but I tend to imagine they need a more thought-out outfit. Would I need better trousers? A collared shirt?
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Looking through its Modern Preppy Collection, though, I’m starting to change my mind. There are familiar boat shoes, but also chunky soles, retro sneakers, and Mary Janes that I can picture wearing with clothes I already own. So this is the approach I’ll take with this collection—start with an outfit you feel good in, then try a different pair of shoes.
Your usual jeans are a good place to start
Boat shoes might bring polo shirts and tailored shorts to mind, but denim gives them a more relaxed feel.
For men, tan boat shoes work with straight-leg jeans, mid shorts and a white T-shirt. Add an open button-down if you want another layer. Dark brown pairs also sit nicely with darker denim and a cream or light blue shirt.
For women, cream boat shoes are an easy match for blue jeans and a striped top. The brown suede styles would work with relaxed denim and a plain white tee, especially if you like keeping your outfits in warm, neutral shades.
The useful detail here is the hem. If your jeans swallow the shoes, try a small cuff. Showing a little ankle or sock gives the pair room to become part of the outfit.
The retro sneakers feel like familiar territory
For men, the cream sneakers work with chinos and a short-sleeved button-down. Brown pairs would look good with beige trousers and a white or navy tee. Both are easy combinations to repeat.
For women, the cream-and-brown sneakers can go with jeans, tailored shorts, or a casual skirt. A white shirt keeps things simple, while a striped top adds a little more personality.
The pink pair is also worth trying with light denim and a white tee. If wearing color feels unfamiliar, let the shoes be the only bright piece. You don’t need a matching pink bag to pull the outfit together but it will also look a bit stylish when you add a nice pair of color-blocked socks.
Try Mary Janes with something other than a dress
I usually picture Mary Janes with skirts or dresses, but pairing them with jeans feels like an easier way to introduce them into an everyday wardrobe.
It would work with shorts, denim, and a tucked-in shirt. For a slightly dressier outfit, try ankle-length trousers and a sleeveless top. If you like visible socks, try a thin white pair with a skirt. With trousers, discreet socks keep the look simple. It’s a small choice, but it can change how playful or polished the outfit feels.
You don’t need a whole new wardrobe
Before choosing a pair, think of two outfits you already own that you could wear with it. That gives you a practical starting point and helps you figure out whether you like the shoes for your actual wardrobe.
I’d still reach for my sneakers and Chucks on plenty of days. But a cream boat shoe or a brown retro sneaker now feels like something I could work into the rotation.
If you’re still wondering whether boat shoes or Mary Janes will work for you, wear your usual outfit when you visit Sperry’s newly opened store on the second floor of SM Mall of Asia’s South Entertainment Mall.
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