Dale’s Bootery

Interviewee: Bob Herald

Interviewer: Kristina Koslosky

Why did you choose to join the Whitewater Chamber of Commerce?

Dale’s Bootery has been a member of the Whitewater Chamber of Commerce for over 50 years! Dale was always a member and Bob continued the tradition. When Bob took over the business, he felt being a part of the chamber was what you did as a business owner in the local community.

Bob has served on the Chamber Board of Directors for over 8 years. More recently, he continues to be involved in the Retail committee and Spirit Tour committee. Maxwell Street days is his favorite chamber event and are two of the best days of the year for Dale’s Bootery!

What benefits have you received through your membership?

As Bob explained, the greatest benefit is “being a member of something bigger than yourself.” The more people that are involved in the chamber, the greater the benefit! The Whitewater Chamber of Commerce opened his eyes to what the community offers. It enabled him to form valuable relationships with business owners and community members. As he highlighted, “We are all in this together!”

What products/services do you offer?


Dale’s Bootery is “an old-fashioned sit & fit shoe store” serving the Whitewater community and surrounding area. We offer a wide selection of shoes for women, men and children – ranging from casual, athletic, work, sandals, and seasonal. Brands: Birkenstock, Chaco, Clarks, Dansko, Earth, New Balance, and Keen.


Dale’s Bootery is not only a shoe store, but also has a connected Pedorthist office. Bob, the owner of Dale’s Bootery, is a certified Pedorthist. He specializes in using footwear, foot orthoses, and other Pedorthic devices to solve problems related to the foot or lower limbs. You can think of a pedorthist as a “foot pharmacist.” Through certification and years of experience, Bob is skilled at fitting footwear, shoe modifications, and choosing the right shoe for you.

To differentiate from big-box retailers while leveraging the owner’s certification and experiences, Dale’s Bootery expanded their service offerings. They include:

  • Shoe Repairs: Dale’s Bootery has been proudly repairing and servicing shoes since 2000 by bringing passion and expert craftmanship to their trade. From sole and heel replacements, to shoe buildups, Dale’s Bootery is here to help!
  • Pedorthic Order Fulfillment: Bring in your doctor’s orders and Dales Bootery can help you with the rest. Through the therapeutic shoe program provided by Medicare, Dale’s Bootery can help qualified diabetics pick out an approved shoe. We also provide 3 pairs of shoe inserts per year.

Additional Services

Orthotics, etc: Dale’s Bootery can help with a variety of pedorthic modifications. They include build-ups, heel lifts, and custom molded orthotics. Other modifications include partial toe fillers and over the counter orthotics.

When you shop at Dale’s Bootery, you get first class services. We are willing to sit down to help you find the right shoe and size. Instead of dealing with a salesman, you can benefit from expert advice. We excel at helping individuals with foot pain find the right shoe.

Dale’s Bootery is the place to go when you are looking for comfort. If you are on your feet all day long, Dale’s Bootery can help you improve your footwear for extra support all day long!

Who do you serve?

Even though we serve the whole family, we specialize in serving customers who need guidance, have foot problems, or have hard-to-fit feet. Dales Bootery carries higher-end quality shoes that suit the unique needs of their customers. If you are looking for comfort, look no further than Dale’s Bootery.

Who is the team?

Dale’s Bootery is owned and operated by Bob Herold, who purchased the business from Dale in 2005. Wendy Koehke manages the Pedorthic Office, while Lindsay Bier manages the store. When you walk into the store, you may be greeted by one of their two part-time sales associates – Deb Olson or Meagan Relitz.

Why did you choose Whitewater?

Bob Herold came to Whitewater in the fall of 1987 as a student at the UW–Whitewater. He was working in food service on campus, but wanted to find another job. He walked into Dale’s Bootery to ask Dale for a job. Bob was relentless and returned another three times that week to pursue a job opportunity.

From 1988 until his graduation in 1991, Bob worked for Dale’s Bootery. He reminiscences of all the times he joked that he’d buy Dale out when he was ready to retire!  After graduation, Bob worked at Kinney Shoes from 1991 to 1994, jewelry sales for a year, and then Famous Footwear in 1995.

Towards the end of 1995, Bob and his wife, Carol, moved back to Whitewater and Bob began working for Dale full-time. Bob had always been passionate about footwear and wanted to help people, so he pursued and earned his Certification in Pedorthics in 2004.

In 2005, Bob purchased the business from Dale and has been a proud owner ever since! Bob and his wife raised their two children in Whitewater and still call it home today. His oldest daughter, Amanda, works at Froedtert Hospital and his youngest daughter, Kelsey, graduated from UW-Whitewater in December 2020.

What is a good referral for you?

A good referral is an individual who is:

  • Looking for comfortable footwear & needs guidance finding the right shoe
  • Has foot problems and needs a Pedorthist
  • Has hard-to-fit feet and needs help finding the right size

Word-of-mouth and satisfied customers are Dale’s Bootery’s best referral source!

Are you an alumni/alumnus of the University of Wisconsin - Whitewater? Do you collaborate or partner with the university?

Bob Herold is a proud alumnus of the UW– Whitewater. By coming to Whitewater for college, Bob met Dale, pursued his passion for footwear and helping others, and ultimately became the proud owner of Dale’s Bootery. His wife and youngest daughter also attended the university. Not only is the owner an alumnus of the university, but also many of his employees! Both Lindsay and Megan are alumnus of the University.

Years ago, Bob worked with Choton Basu and the student organization, Enactus. The Enactus group of students created the current Dale’s Bootery logo, provided recommendations on store improvements, and crafted their window display.

How has the Safer from Home order impacted Dale’s Bootery?

Once the Safer from Home order went into effect on March 25, 2020, Bob unfortunately had to furlough his employees. For the first 3 weeks or so, Bob ran the store by himself – checking messages, answering calls, shipping/delivering shoes, etc.

Fortunately, Dale’s Bootery got their online store up and running quickly with Shopify so that customers can conveniently order online! The company’s latest and greatest achievement is moving into the 21st century with an online store! Shop their online store: https://dales-bootery.myshopify.com/

By the week of April 20th, Bob will be able to get his employees back on payroll – thanks to the Paycheck Protection Program!

As Bob explained, “To be honest, this shut-down reinvigorated me. Now, I am the only one working and am going back to my roots.” For over 35 years, Bob has been doing this and still loves it. He chooses to own his shoe store in Whitewater so that he can help his customers rather than treating them like a number as a corporation would do. Dale’s Bootery loves their customers and truly views them as friends!