How Three Milwaukee Streetwear Brands Made 414 Day Unforgettable

The line wrapped around the block outside Unfinished Legacy’s shop on 414 Day with a feeling of anticipation. A mix of families, curious individuals, and fashion lovers stood avidly ready to celebrate Milwaukee through its local style. I was handed a raffle ticket for a free printed shirt, and when I finally stepped in, I was hit with a wave of music from the DJ booth and the sound of chatter everywhere.

A mother and her twin daughters stood in front of me, their matching orange coats and short bangs catching the sunlight. They were there for the same reason as everyone else: to be a part of something that felt bigger than just clothes — something that felt like a community.

Every year on April 14, Milwaukee honors its area code with a citywide celebration of local pride. This year, three homegrown streetwear brands, Unfinished Legacy, Click Kicks, and 414 Milwaukee, turned the occasion into a full-blown cultural moment with product drops and community events. From custom sneakers and half-priced clothing to culturally themed bomber jackets, each brand was united by creativity, authenticity, and deep-rooted love for the city.

Unfinished Legacy: A Streetwear Family Cookout

At Unfinished Legacy, the crowd came early and stayed late. The shop was busy. Shoppers browsed racks of trendy jerseys, colorful T-shirts, and cozy sweat sets, each featuring the brand’s name in large print, as music blasted, and custom shirt pressing was happening in real time. One of the co-owners, Brema Brema, known for having his work for Unfinished Legacy featured in Vogue, was pressing shirts himself, unwaveringly focused despite the long day. Everything was half off, and shoppers, young, old, and everywhere in between, walked out with arms full of the streetwear brand’s merch.

The shirt-pressing line quickly became a spot for spontaneous connection. I struck up a conversation with the mother of the twins, and later, my friend and I danced with the girls, teaching them some classic Milwaukee dances, while DJ BAMN kept the energy high, playing local rap music that captured the spirit of the city.

“The girls are excited to pick their designs and watch their shirts get ink pressed right in front of them,” their mother told me. “I was downtown for 414 Day, saw the line, and immediately knew we had to come. I love supporting local, especially something that lets my girls feel excited and included.”

Click Kicks: 414’s Sneakerhead Holy Grail

Meanwhile, across town at Click Kicks, shoes sold out fast, including a limited drop of just 200 pairs of a new Adidas collab designed by founder Eric “Shake” James, a Milwaukee native with deep roots in the sneaker world. His nephew, UWM graduate Jaison James, helped manage the store.

“Shake used to run with Run-DMC back in the day,” James said. “He’s had a relationship with Adidas since the ’80s, and this is actually his fourth Adidas shoe. Every pair he makes is inspired by Milwaukee. The colors, the skyline, and the culture.”

This year’s design included details such as cheese graphics on the tongue, nods to the Milwaukee flag, references to beer and bowling, and even Marquette colors. One visitor, the grandson of the designer of the original Milwaukee flag, showed up to purchase a pair and share his family’s story. By the time I arrived, the blue drops had already sold out, but people were still coming in just to see the shoes and soak up the atmosphere.

While I interviewed James, a woman with a British accent walked into the store and asked for the popular blue pair of 414 shoes. She was politely informed they were sold out. Her disappointment was a reminder of how far Click Kicks’ influence had spread beyond the city, reaching sneaker enthusiasts from across the pond.

Click Kicks had hosted a free tattoo event on April 12, complete with a live DJ, a local artist who offered Milwaukee-themed ink, and a designer to do custom shoe artwork on-site from Adidas. As a sneakerhead with a newfound love for the store, I was sad to have missed it.

“We’re the only licensed Adidas retailer in the city,” James explained. “People think you have to go online or pay resell prices, but we keep everything retail, no markups. Shake came from the Boys and Girls Club. He grew up in the city and gives back every chance he gets.”

414Milwaukee: Milwaukee Pride Personified

That spirit of community was on full display at 414Milwaukee, a local brand that wears its area code like a badge of honor. Known for bold, minimalist designs rooted in civic pride, 414Milwaukee used this year’s collection to highlight the connections between culture, family, and local identity with Milwaukee-themed t-shirts, jackets, crew necks, basketball jerseys, beanies, and caps.

I was not able to make it to the 414 Day flag drop ceremony. I wanted to ditch my on-campus job making coffee for caffeine-deprived students, but the broke college student in me remembered that life isn’t free and waited to join the day’s festivities after work. Still, I caught up with founder Fred Gellich over email to learn more about their release.

Their latest drop paid tribute to Milwaukee’s deep roots, including a nod to the Native Americancommunity whose history shapes the city. A standout piece featured the numbers “414” integrated into the design of a trail marker tree, a tribute to the one located on the grounds of the Indian Community School.

“There’s no big message,” Gellich wrote. “Just proud to be a Milwaukeean.”

His favorite piece of the collection was a clean, bold 414 bomber jacket, designed to be worn with confidence, but without needing to say much.

“When you look good, you feel good,” Gellich added. “And when you feel good, you can accomplish anything you want.

Whether it was six-year-olds learning dance moves, shoes selling out in hours, or apparel that showed the pride of the community, 414 Day was more than a shopping experience. It was a portrait of the city’s fashion community that showcased the diverse, vibrant, creative, and deeply proud culture of Milwaukee.