This summer, I’ve found myself a little frozen. Fashion magazines have left me feeling uninspired and bad about myself, and I’ve come to a style crossroads whereby the simplicity of a uniform is sounding unusually refreshing. So perhaps it was serendipity when Leandra reached out and asked that I style a story around Waldo, the preeminent uniformed character of my childhood storybooks.

Waldo has committed to one look for as long as I’ve known him: red Breton stripes with his signature beanie and classic straight-leg blue jeans. There are numerous prominent cultural figures — both fictional and not — who have similarly committed to a look. Whether their style leans simple and utilitarian, like Fran Lebowitz’s, or eccentric and over the top, like Iris Apfel’s, one could argue their chosen uniforms have further solidified their status as iconic.

Uniform dressing can also serve a more practical function. In his Vanity Fair profile, President Barack Obama famously said he wore the same thing every day for the sake of productivity. “You’ll see I wear only gray or blue suits… I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.” My husband, Waqas, and I talk about this all the time. He claims that editing our wardrobes to a science might free up our creative minds.

As appealing as that sounds, I haven’t always felt inclined to take the minimalist plunge. Maybe I’m loath to settle into a lane because I have yet to find my own personal style, and getting dressed feels like an endlessly fun experiment of self-discovery. The older I get, the more I believe this journey is continuous, the lessons ongoing — with no end in sight. I’m not sure I’ll ever be ready to opt out. The all-you-can-eat fashion buffet is vast; how can you not give everything a taste?

My stylistic freedom also serves an emotional purpose. I love looking back and getting reacquainted with the variety of Anums that have unfolded throughout my life. They’re like characters that tell a story of who I was at the time, where I was going, how I was feeling, what I could afford. Not every style decision may have been worthy of applause, but clothes are remarkably nostalgic. Flipping through my sartorial past feels like going through an old family photo album. The bad outfits will always make me smile.

Historically, my deepest uniform aversion stems from the fact that I went to a staunch private high school that enforced a strict (and frankly, ugly) uniform. Wearing a charcoal gray pencil skirt with a white button-down for four straight years killed any fashionable leanings I may have experienced from the ages of 13 to 17. When I graduated in 2004, I swore I was done looking the same every single day.

Considering this evolution of my feelings about uniform dressing, I was intrigued by the idea of applying my typically maximalist styling approach to Waldo’s minimalist concept of dressing. So I took Leandra up on her challenge. I dove head-first into every striped garment I owned and emerged with five outfits that combined Waldo’s comforting rubric with my buffet-dressing sensibilities. It turned out to be just the green light my style crossroads needed.

Photos by Waqas Farid. 

Anum Bashir is a Doha, Qatar native currently living in Dubai. She’s the Founder of Desert Mannequin, podcast host, fashion and brand consultant and co-creative director of NDUO. 

Man Repeller editors endorse products we genuinely love. If you end up buying something through our links, we may earn an affiliate commission. Learn more here.

Get more Fashion ?