#AlwaysAndersonville: The Podcast – Show notes from Episode 72 with Kaleb Sullivan of Dearborn Denimn

This week, Laura and Sara are joined by Kaleb Sullivan of Dearborn Denim. Dearborn Denim offers the most curiously comfortable jeans imaginable at the best price possible. Everything is cut, sewn, and crafted at their factory in Chicago with the best American made materials and can be custom hemmed to fit at their Andersonville location at 5202 N Clark.

Plus, Dearborn Denim is hosting Urban Renewal Brewery for Taste of Andersonville tomorrow on August 7! 


Kaleb Sullivan in Transistor before recording this week’s episode.

“There are not a lot of neighborhoods that support small businesses, especially on the locally-made front, like Andersonville.”
– Kaleb Sullivan

Listen to Episode 72 with Kaleb Sullivan!

Here are some references from Episode 72 that you may want to check out:

  • Kaleb was born and raised in Chicago in the Bucktown neighborhood. He even lived nearby Andersonville at Lawrence & Ashland immediately after moving out on his own. He’s never lived outside of Chicago!
  • Dearborn Denim was formed in 2016. Founder Rob McMillan who set out to make the perfect pair of jeans for his wife after she felt dejected trying to find jeans that were “affordable, ethical, and sustainabley sourced.” He started with only two different cuts, and the company has since expanded greatly. Check out their different styles here.
  • Kaleb met Rob for the first time at a street fest in 2016. They were vending next to each other at the fest – Kaleb was selling jewelry at the time – and Kaleb couldn’t believe that Rob was selling Made in Chicago jeans for only $49, at the time, and they struck up a conversation about Rob’s company. They kept in touch and Rob reached out to Kaleb to offer him a job when he was ready to open the first brick and mortar. 
  • Rob figured out how to make jeans after talking with a lot of local designers and local stores and was fueled by his drive to succeed and learn. The biggest feedback was customers wanted something comfortable, which lead them to their signature stretch denim. 
  • Dearborn Denim’s sewing team at the factory started with just three people, and now they currently employ 25-30 in the factory. The stores employ another 10 employees. Rob’s goal is to eventually give jobs to at least 100 Chicagoans. You can even tour their factory! Schedule here. 

Inside Dearborn Denim.

  • While Dearborn Denim’s first storefront is in Hyde Park, the company was inspired to open in Andersonville because of the strong local ethos here. Hyde Park is also very far south and east, and they wanted something also on the North Side of the city. View locations.  Andersonville’s location opened in May 2018.
  • Sara recalls fondly when AKIRA (5228 N Clark) was first looking at Andersonville and the utter surprise and delight their team felt at stepping into Andersonville for the first time, having originated out of Hyde Park as well.  
  • Dearborn Denim, located at 5202 N Clark, is a lovely space that even the Chamber has used in the past as headquarters for Arts Week in 2017. Kaleb mentions that the arrow on the street sign really won them over on location. 

Dearborn Denim staff during Andersonville Sidewalk Sale 2019.

  • When a customer comes in to purchase jeans, the Dearborn Denim staff is there to custom hem each and every pair length-wise on the spot. Most jeans take only about 10 minutes to hem. 
  • Kaleb touches on “the retail apocalypse” – He doesn’t think retail is going anywhere, not while people still feel the need to go in and touch, feel and try on the product. Especially with jeans, customers are so intrinsically invested on finding the perfect fit. Once a customer is established in the Dearborn Denim system, however, they can continue to shop their choices online since fit has already been established. Kaleb feels Dearborn is fighting the “apocalypse” by inviting other local, creative entrepreneurs and designers in for pop-ups, events and collaborations at their storefront.

Stillhouse Whiskey partnered with Dearborn Denim during Arts Week 2018 for their artist party.

  • Dearborn Denim jeans were once carried by local retailer Milk Handmade (5137 N Clark). Since opening their own stores, they don’t often have products in other shops, but certainly value the relationships they’ve built.
  • Dearborn Denim is looking to open one or two more storefronts by the end of 2019! They are looking at both a South Loop location and Lincoln Park location.
  • The V2 wash is also a new wash that Dearborn Denim has just released. They have also developed new products like t-shirts and the Commuter jean. The Commuter is designed with the cyclist in mind and has a tighter ankle to avoid getting caught in the gears, a darted knee for extra moment, a more padded seat, angled pockets and a higher waste. 
  • Dearborn is also considering more levels of customization, including customer-designed distressing; think ripped knees, blown out pockets, and bleached legs. Kaleb also jokingly talks about “heritage jeans” with a large buckle on the back to let out the waist.
  • Denim on denim or “the Canadian tuxedo,” as Kaleb calls it, is something that Dearborn has considered when it looks to a future of making denim jackets and shirts. Right now, though, they are focused on making sure they can keep up with pants orders. 

“As long as you’re clean, your jeans are clean. If you wash your jeans more than one time every 10 wears, that’s way too much – fun fact.”
– Kaleb Sullivan

  • Kaleb says the life expectancy of jeans really depends on the wearer. The heavy wearer’s pair could last 2-3 years, but if the wearer is swapping out and taking care of their pants, jeans can last up to a decade. Jeans need to be washed cold, inside out and hung to dry. The very dedicated washer could even go as far was washing them by hand, in a tub at low water levels. There are even detergents that specialize in dark wash, like The Laundress, a denim wash made out of Brooklyn. Kaleb says you do NOT need to put your jeans in the freezer to clean them. 
  • If given the opportunity to switch places with another Andersonville business, Kaleb would choose four: Transistor (5224 N Clark), Strange Cargo (5216 N Clark) because Kaleb loves the aesthetic in there, Candyality (5225 N Clark) even though his dentist wouldn’t appreciate it – shout out to 1st Family Dental (5333 N Clark), and Village Discount (4898 N Clark) so he could be a sorter in the back. 

Even elves need jeans! The Elf on the Shelf Tommy Hall visited Dearborn Denim during the Late Night Andersonville 2018. Photo by Thomas Bock.

Visit Dearborn Denim on the following platforms:
Online: dearborndenim.us
Facebook: facebook.com/dearborndenim
Instagram: @dearborndenim

This week’s episode is sponsored by locally-owned Pearle Vision on Clark & Lawrence at 4818 N Clark.