After first opening its doors in 1970, Dale’s Bootery will be closing those same doors in the near future. The business has been helping the Whitewater community purchase shoes and create connections for over 50 years.
Forty years ago, Dale passed the business over to employee Robert Harold, who has run the business since. As a UW-Whitewater alumnus, Harold found his place in Whitewater during his freshman year.

“I worked at a shoe store when I was in high school,” Harold said. “When I came to school in Whitewater, I worked a couple jobs on campus and I decided that wasn’t what I wanted to do for four years. I noticed there was a shoe store in town, so I came down and I applied here, and I think I bugged Dale long enough to hire me.”
But after many years of working and running the business, Harold felt it was time to step away and continue his life and passions elsewhere.
“I’ve loved doing this,” Harold said. “I worked at a couple of chain stores and corporate, and it was not real personal. But that’s what’s wonderful in a small town and owning your own business is building relationships with people… it’s just time.”
Harold has seen how Whitewater has changed throughout the years and how the city has grown its connection with the university.
“It has been kind of nice seeing the attitude, even toward the university, change in the years I’ve been here,” Harold said. “I mean even as a student at UW-Whitewater, it was sometimes an ‘us against them’ feeling between residents and the university, and I don’t feel that anymore. I think it’s a much more accepting and tighter community.”
Harold has also seen trends in shopping change. From less weekend foot traffic to losing business to online shopping, these trends have affected his business.
Many long-term Whitewater customers are sad to see the Bootery close, as it is a pillar of the city.
“It reminds me of the hometown I grew up in,” Whitewater resident Peter Jordan said. “There’s a high level of personal service here and trust that you don’t get at your average store. It’s a real human being who knows his trade, knows it extremely well and doesn’t push a product. He directs you to products that might help you.”
Harold is excited to see the next chapter of his life open up and reflects on the place of peace he brought to the community.
“I would hope that we did a good job of making everybody more comfortable and doing right by the community,” Harold said. “We’ve always tried to give back when we could. I hope people had a good experience shopping here and have good memories of the store.”
