Radiance despite gray weather – Chicago Reader

The vernal equinox has happened for 2025, which means that spring has finally arrived. However, we could call it a “technical spring” so far because we’ve only had fleeting glimpses of the warmth and new growth yet to come. 

Right now is the time of year when Chicagoans crave color. While nature will take its own time to dazzle us, we can always choose to wear clothes for the season we want to be living in. 

“It was such a dreary day that I wanted to wear colors that cheered me up and popped out against the gray sky,” said Jeffrey O’Malley. O’Malley and I emailed after I ran into him at a bus stop this month. The 34-year-old candle assembler continued, “I also love nodding to Piet Mondrian in outerwear when I can by wearing primary colors.”

Photographed on his way home from work, O’Malley appeared both cozy and sophisticated in a carefully coordinated yet effortless ensemble. His attention to detail was evident in every piece.

O’Malley was able to supply us with a detailed list of sources for his outfit. “The day you saw me, I was wearing a vintage wool flatcap by Kangol that I found a few years ago at Andersonville Antiques, a cherry-red chore coat by Le Mont Saint Michel (which I was thrilled to get on sale), a vintage indigo scarf I bought from Kopi Cafe’s boutique, Navajo-Churro wool mittens made by the Weaving Mill in Humboldt Park (I really admire Emily and Kendall there and urge people to support their work!), Todd Snyder checked wool pants from eBay (which a coworker kindly hemmed), and my umbrella was left behind by an old roommate . . . as it falls apart, I continue to repair it,” O’Malley shared. 

“My style tends to be eclectic and textured and primarily influenced by what I find at thrift stores, antique shops, or the rare online find on eBay,” he added. 

Despite his keen fashion sense, O’Malley admits that shopping for clothes isn’t something he particularly enjoys, and his wardrobe has been built over time. “I used to live near Unique on [Elston between] Irving Park and Addison. That place had some beautiful men’s clothes. Brown Elephant in Andersonville will have good finds. Uniqlo has pants that fit me, given how short I am. Otherwise, I browse eBay every now and then.”  

When it comes to style inspiration, O’Malley credits his grandmother Iris, and his wife, Heather, both of whom are “exceptionally stylish.” “Also watching films from the 60s and just paying attention to people [in my age range] working in coffee shops. I tend to prefer playfulness and pieces that will last [instead of] trends,” he said.

Though his bus arrived quickly, O’Malley and I got to chat for a bit while I took his photos. Before boarding, he mentioned that I couldn’t send the pics to his phone, which is as low-tech as possible. “Technology is great but only insofar as it serves human connection,” he emailed.

“Not having social media, I feel like I have to look at the world around me for inspiration. I look to my friends and my fellow Chicagoans as much as I look at styles prevalent in older films and in art history. Sometimes, my favorite color combinations come out of European medieval art. Sometimes, in reading a book, an article of clothing gets mentioned that stands out and draws my attention.” 

To elevate one’s style, O’Malley suggests looking at art and observing how painters use color. “Also, it’s always refreshing to step outside the box and experiment,” he wrote.

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