Behind The Design: Our Signature Boots


We’ve all done the shoe shuffle in front of the mirror—slipping on ankle boots, then flat Chelsea boots, then heeled Chelseas, searching for the perfect way to finish off an outfit. Picking the right pair is the difference between a “…” and a confident “!” for your outfit.

And once you’re out the door, that may be the last you think about what’s on your feet, but our shoe designer Nilunda goes through a head-spinning process to perfect every single detail. When she set out to make this fall’s boots, we asked if we could look over her shoulder every step (lol) of the way. Here, she explains her process, how she keeps things as old-school as possible and why a leather sole actually matters.


You designed our most famous shoe, The Billie Boot. What was on your mind at the time?

Nilunda: When I designed the Billie a few years ago, we were really into the importance of having a style “uniform.” You have your favorite pair of jeans—what’s the boot you want to wear just as often? So I combined elements that can’t really be pegged to a certain time or style, like a rounded toe, a hidden inner zipper and a really simple upper—everything above the sole. I also made sure it’s comfortable. No matter how great a shoe looks, you won’t wear it if you can’t walk in it.

It’s a new season. What’s the very first thing you do?

Our entire design team starts each season with mood boards. We share our inspirations for colors, shapes and ideas for everything wearable from head to toe. I think about which shoes you already have and love and create something you actually need. It’s not just making new shoes for the sake of it.

What’s your process like?

I start sketching the shoe’s last first, which sounds funny to say. A last is a wooden model of the way a foot will fit inside the shoe. It’s where you pick the toe shape, and the curve, the heel height. From there, I add in the details like zipper or buckle placement and then pick the leather. In fittings with the first samples, I get right up in there and cut the shoe or draw on it where we want to adjust. You can’t be afraid to ruin your samples. It’s how you get to the perfect finished product.


This sounds super hands-on. Does digital design factor in?

I really try to keep it as old-school as possible, so I’ll always prefer a pencil and paper over a screen. There’s so much freedom in drawing a shape rather than using a computer program. You can really nail the exact curve of a last or the tiny little decorative stitches called tacking.

What details are you obsessing over right now?

A leather sole is one of the most important—yet invisible—parts of a good boot, and all of ours have them now. A natural material sole, instead of plastic, is more connected with the feel of our bags. The Transport Tote, for example, is all natural leather.

If we need just one new boot this season, which is it?

The Frankie Chelsea Boot, definitely. It instantly makes every outfit cooler. It’s slimmer than a standard Chelsea and has a longer but still rounded toe. The boot hits above your ankle so it’s a perfect match for cropped pants which certainly aren’t going anywhere just because it’s getting colder. That said, I love them all!

No matter what boots you’re wearing, we want to see ’em—you could win a $2,000 Madewell shopping spree and everything you need for a perfect day of strolling: two pairs of boots (your choice), headphones from Grado Labs, a year of Spotify Premium, a water bottle from Mizu and snacks from Baked.* Be sure to tag your pictures #wellheeled and #contest. Now get to stepping.

Shop our Boot & Shoe Shop here and our jeans and denim here.

*Open to legal residents of the 50 United States (D.C.), 18 years or older. Enter Contest by 11/14/16. For Official Rules, including prize descriptions, visit Void where prohibited.

Photography by Jennifer Trahan & Angi Welsch.