These Sneakers and Flats Are the Key to Every Cool Fall Outfit

Is it just us, or are high heels simply getting less play in our everyday outfits these days? If we’re putting our arches through it, we’ll usually go kitten heels or bust. In place of high heels, walkable flat shoes have become the cornerstone of our wardrobes. While there are loads of stylish options on the market, we love the idea of adding our Who What Wear point of view to the conversation. You may remember when we debuted our Sperry collaboration with a pair of all-weather boots last October. The chic rain/snow/sun stompers sold out quickly on Sperry’s site, and now, we’re back for a little more collaboration magic. But this time, we’re debuting two special styles: suede sneakers and leather mules. Let’s dive into the sneakers first with a peek at the design process and standout details.

Our editors are longtime fans of Sperry, and while the classic boat shoes will always be iconic, the Freeport Sneakers have a special place in our fashion-loving hearts. Unsurprisingly, influencers have also adored the retro style since it came out, cementing it as one of Sperry’s core offerings.

Since the Freeport is an existing style, we were lucky to begin with the shape and some characteristics of the shoe style already in place. When it came to color and material, though, we went through many iterations until we struck shoe gold. We played with beige, tan, sand, cream, white, and every combination thereof until we landed on a pairing that felt harmonious and interesting.

After seeing a sample IRL (always a thrilling moment), we decided the shoes felt a little one-dimensional, so we added some depth with a textured material. Gold shoelace eyelets were a subtly chic addition that aligns with the gold jewelry our readers love to wear. Lastly, rather than a printed Who What Wear "W” logo, we decided to render it in understated embroidery that matched the shoe color—a little quiet-luxury moment, if you will.

Premium suede and a woven upper with a mesh-like effect make these sneakers stand out from the pack. The colors of sand and warm cream create a dimensional, tonal look that’s enhanced by the texture throughout.

SHOP THE SNEAKERS

HOW TO STYLE THEM

The Freeport has a retro feel, so Editor in Chief Kat Collings wore an outfit that references Princess Diana’s iconic ’80s sneaker style. The white socks add a sporty element, which is then contrasted with the preppy cardigan and prim skirt. It’s the wrong-shoe theory in action!

It doesn’t get more classic than a white button-down, jeans, and sneakers. We love how associate editor Chichi Offor wore a silver metallic bag to add a trend-driven element.

Who said Bermuda shorts can’t be office appropriate? The best looks are a study of contrasts, and the vibe of a polished blazer and turtleneck against cutoff shorts and sneakers is transitional-outfit perfection.

While the sneakers are a fresh take on an existing style, for our second shoe style, we wanted to add something new to the Sperry world. One of the things we love about collaborating with Sperry is the brand’s open-mindedness to experimenting and letting its partners help guide the creative conversation. Enter the leather mules. There’s nothing easier than slip-on shoes, and we wanted to do our own take on the flat-clog-mule trend. With fall quickly approaching, we thought a faux fur–lined footbed would make these wearable, cozy shoes irresistible.

Our sketch initially featured a slightly chunkier sole, but then Sperry showed us a sleeker archival outsole from the iconic Captain’s Oxford designed by Paul Sperry in the 1930s, and we fell in love. The result is truly a marriage between Sperry’s rich heritage and our Who What Wear point of view.

When we got the samples back to review, our design notes were rather limited because the shoes were already so gorgeous! We wanted to remove the tan stripe on the sole and add our label. We were so impressed with the faux-fur option Sperry presented. The color was rich and deep like the colors on our inspiration board, and the feel was incredibly luxurious.

The result is incredibly comfortable mules that come in black and ivory leather. The contrast stitching has kind of become our signature. It’s a nod to our first boot style, which featured the same design detail.

SHOP THE MULES

HOW TO STYLE THEM

Collings loves mixing a variety of ivory shades and wanted to play with the juxtaposition between a sophisticated, pretty skirt and blouse and more utilitarian mules.

Denim maxi skirts are one of the reigning trends of the year, and as you can see here, they pair perfectly with our leather mules. We love how the unfinished hem draws the eye down to highlight the shoes.

You can always count on our editors to model the best trends of the season, and vests are one of those It items with a lasting impact. A vest worn with a slip skirt and our leather mules creates a sleek and polished look.