DrawTogether with WendyMac

DrawTogether with WendyMac

DT Grown-Ups Table

Day 23. Shoes!

Sometimes a shoe isn't just a shoe.

Wendy MacNaughton's avatar
Wendy MacNaughton
Jan 23, 2026
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My 30 day GUTsters!

You are three weeks in — three-quarters of the way to 30 days of drawing!! You are doing great!

And we only have a couple more delights to celebrate before we change gears, so let’s do an extra fun one today. Yesterday’s clothes shared SO much more than I ever expected. So much love and care and story and silliness in those drawings. So much DELIGHT. Today, we go deeper into the sartorial world and find delight in….

Shoes.

Sneakerheads, shoe collectors, footwear enthusiasts, heel-aholics, foot fetishists (oh, wait, that’s different) — call it what you will, people LOVE their shoes.

Myself, I don’t care all that much. At any given time, I have two or three pairs of shoes on rotation and I wear them everywhere, from ballroom to bedtime. Currently, I’m kicking around in a pair of cheetah/flame print slip-on sneakers, lace-up black boots (aka 90s “sh*tkickers”), and sheepskin slippers I’ve been shuffling around in for nearly eight years. However. These are just the current players.

Back in my closet, a team of shoes wait patiently to be called into the game. There are the aspirational designer heels. And the highlighter yellow lace-ups that seemed like a fun idea at the time. Or the stacked heels I got married in. And of course my favorite hightops that are worn to shreds but I refuse to retire. All those shoes are fun to look at. But more interestingly, they tell a story when you look closer. It’s written on their soles, on their scuffed suede, on heels worn down so differently I wonder how I waited so long to get that hip replacement. Turns out you don’t have to walk a mile in my shoes to understand me. You can just look at them.

It’s not just me. All of us have shoes that tell a story.

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Shoe portraits for drawn journalism stories

The first couple I’ll share come from some stories I’ve published. They hold so much meaning and delight for me. When I am researching a drawn journalism story, I have my art eyes permanently open. It almost feels like I’m looking through a finder at all times. That’s how I spotted these subjects.

Sean Thackrey’s boots, from “The Bolinas Winemaker,” Pop-Up Magazine

I was fortunate to spend a few days hanging and out drawing with the infamous California winemaker Sean Thackrey (1942-2022) to create a story about his unique approach to winemaking. Exploring his house, I spotted these dirt-encrusted and wine-stained boots by his front door, waiting quietly, ready to go to work. I did some sketches, snapped some photos, and painted the boots when I got back home. I always thought these drawings were apt portraits of Sean, and captured more than a simple drawing of his face.

Don Walker’s boots, from “The Bootmaker,” New York Times.

Another very different sort of boot portrait were these cowboy boots, handmade by the subject of one of my New York Times stories, Don Walker. (You can read the story here.) Don is a bootmaker in Southern Utah, and it was a real honor to spend the day with him and learn how he stitched these boots together — all the care and love that went into creating them, and how he’s passing that knowledge onto his son.

Andy Warhol

Warhol Shoe Drawings

We can’t talk about shoes without looking at Andy Warhol’s shoe drawings. Andy is famous for his pop art, but IMHO his best art is his illustrations, especially his many drawings of shoes. Before Warhol took over the art world in the ‘80s, he illustrated for magazines, including a shoe drawing every week for an ad in The New York Times. (Warhol was known as the less political Ben Shahn.) Here is a smattering of his shoe drawings he created that I find ridiculously fun and inspiring.

Jeffrey Gibson and John Little Sun Murie

Candace took this closeup of a shoe from a piece at Jeffrey Gibson’s solo exhibition at the Broad museum in LA. The piece lives at the Brooklyn Museum.

Jeffrey Gibson incorporates footwear into his artwork, often collaborating with Indigenous artists, like John Little Sun Murie. In this piece, Jeffrey and John created custom beaded moccasins to adorn an early 20th century bronze sculpture of a Native American, altering the whole feeling of the piece. Jeffrey considers these shoes spiritual objects and conceptual art pieces — they incorporate traditional Native aesthetics with contemporary queer and popular culture. A whole lot more than a pair of shoes…

Sometimes a shoe is more than just a shoe…

With that inspiration, time for today’s DELIGHTFUL drawing assignment.

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