*this post is in partnership with Sperry, but as always, I’m giving you my honest opinion

As I’m sure anyone could imagine, becoming an iconic piece of fashion history is no easy feat. Sperry has managed to tackle this feat with their timeless Top Sider. It’s simple, it’s functional, it’s classic. Yet what I love about this shoe the most is it’s unexpected versatility.

While we’ve all been somewhat sidelined (or home-lined, perhaps?) during Covid-19, one thing that I’ve been focusing my energy on while self-caring at home is my style. What’s working? What’s in need of an update? What’s in need of removing altogether? What I eventually came to was that keeping things in my closet that don’t serve a multitude of purposes no longer seemed efficient. Be versatile or be gone.

Cue these Sperry Boat Shoes from the recent John Legend Edit. They’re a classic brown on brown color, which works with just about everything I wear during spring and summer. They’re soft right out of the box, but I started to wear them around the house to really break them in as much as I could. Now that they felt great on my foot, it was time to see how I could style them.

For the sake of versatility, I decided to style them in 3 different ways. One extremely casual summery look, one mid-level upscale casual for a spring night out, and one for the off-chance that maybe I’ll get invited to a yacht party this summer. Let’s delve into each…

In the first, highly casual look, I started with my Sperry’s, then realized that I wanted to push away from the norms of what you’d expect to see paired with a boat shoe. This led me to some cut off jean shorts (as opposed to the traditional chino shorts), a lightweight tank top, and a linen short sleeve button up shirt.

This is the type of look that can take you just about anywhere on a summer day. I could start at the beach with my shirt opened wide and end at a dinner with my shirt buttoned up and fit in everywhere, all while staying totally comfortable on my feet thanks to the shoes. Embracing classics isn’t always easy for me because they can feel a bit too “expected”. Moving away from the norm while also maintaining some style is an excellent move that I would recommend to anyone.

In the next, upscale casual look, I followed suit and decided to recognize what might normally be paired with a boat shoe and move in the opposite direction. Styling from the floor up, I started with the Sperry’s. I also opted for a slim dark denim as opposed to a traditional chino pant, a club collared short sleeve seersucker shirt, and a lightweight suede motorcycle jacket rather than the typical cotton blazer or sweater we’ve all become accustomed to seeing boat shoes paired with.

This is a look that I would wear to just about any casual dinner or evening out. It’s an edgier take on a classic that still feels remarkably clean to me, which I love. Understanding that making minor adjustments to classic looks can lead you down a really interesting and fulfilling style path is always beneficial. Also I must mention the versatility of the shoes allows you to do so quite easily.

Finally, my yacht dreams personified. Boat shoes work wonderfully with a suit, as long as it’s tailored slim and perhaps a bit cropped. This cobalt blue suit makes a statement all on its own, but adding the classic boat shoes into the mix works nicely. I finished the look with a clean white tee and a maroon neckerchief to really embrace the summery boat life vibes of a look that would absolutely turn heads nearly anywhere its worn.

Once again, you can see that by choosing a bolder suit, switching in a tee for a linen or oxford shirt, and adding in the neckerchief as opposed to a traditional tie or bow tie, I’m staying within the same world but making it a lot more modern and cool. I’ve put my own twist on things as opposed to sticking within the expected confines and thus my style is expanded.

Styling classics can be a lot of fun. If you’re interested in turning heads and trying something new, I say go for it. However one of the greatest things about an icon like the Sperry Top Sider is that it also works in all of the slightly more expected ways as well, which brings it all back to where we started…versatility.

Check out the whole Sperry x John Legend Edit here. It’s amazing, there are a lot of awesome styles.

Thanks for reading! Questions? Comments? Find me on social media @parkeryorksmith or email me directly at parker@thelooksmith.com!