Taking to the Streets

Meet Drew Westphal, a Milwaukee blogger who helps us showcase March’s military-inspired styles

IN 2013 DREW WESTPHAL began posting photos of his outfits online, casually beginning what by 2015 would become a full-fledged style blog called “Everyday Drew.” His interest was piqued by a pair of black-and-white Air Jordan sneakers seen in the basketball god’s 1996 film debut, Space Jam. His love for sneakers eventually turned into a love for styling. Today the blog features snapshots of Westphal’s outfits taken by friends – or with the help of a tripod – around Milwaukee. And his aesthetic, which he describes as “Japanese minimalism and American workwear,” has earned him a national following. According to Westphal, a surprising byproduct is that many of his followers in exotic coastal locales are now curious about Milwaukee after seeing it as the backdrop to his blog photos. “They never thought it could look so cool,” he says. On Drew (left): Olive nylon bomber jacket, $60 at Midweight denim shirt, $79 at J. Crew. Martin denim pants in Bodie wash by Raleigh Denim, $285 at Milworks. 1970s All Stars by Converse, $90 at

On Elisabeth (above): Boyfriend denim jacket by Citizens of Humanity, $379; Red bomber jacket by Likely, $249; Lace-up top in olive green by Lumiere, $129; Faux suede jogger pants by I Love Tyler Madison,

$149; Fringe bucket bag by City Spot, $89; Open-toed suede shoes by Schutz, $99; all available at Stephanie Horne Boutique.