A Woman's Guide to Getting Your Male Boss to Wear Women's Shoes

Chief Steve Roos walks down the street during the DVSAC's "Walk a Mile in Her Shoes" fundraiser.

IFPD Detective Pat McKenna selected a lovely pair of turquoise shoes to walk in on Saturday. He later sported a few new blisters. 

IFPD Detective Rome Stiffler definitely did not chose anything subtle for his debut in the "Walk a Mile" fundraiser.

Post by Joelyn Hansen
My abilities amaze me. I’m not bragging, but it’s not every day you can manage to get Chief Roos (my boss) to wear a pair of women’s shoes for the “Walk a Mile in Her Shoes” fundraiser. Something others failed to do in the past!

The Chief supports the Domestic Violence and Sexual Assault Center, but he’s not crazy about having sore feet. So, it took strategy and the right pair of shoes in the zero hour to get him to do it.

The DVSAC’s  “Walk a Mile in Her Shoes” fundraiser is one of, if not the, biggest fundraisers the center hosts.

I LOVE this fundraiser. It’s a for a good cause and it’s a good time watching men hobble down the street in high heels. Did I mention that some of these shoes look like something a drag queen would wear on the Vegas Strip?

IFPD Detectives Pat McKenna and Rome Stiffler were participating and I naturally thought the Chief needed to take part too.

My “woman’s training” would need to be used to coerce him though. Everyone knows a determined woman can get a man to anything – just ask Adam about the moment he and Eve got kicked out of the garden.

While the chief was on vacation I placed the registration envelope in his box with a post-it note attached that said, “Have you ever considered doing this? It would make for a good blog….”

If you haven’t figured it out yet, the Chief loves to blog and if anything were to push him to wear ladies’ shoes it would be in the name of the blog!

The Chief started to bite the bait. But, before agreeing, he countered with, “Find me a pair of shoes that I can wear and I’ll do it.”


Two days prior I sifted through size 14 shoes and selected a few pairs – including a pair of red patent leather high heels made for an Amazon woman – for the chief to try on.

The red heels (which I knew he wouldn’t wear) laid the ground work to get him to finally choose a pair of flip flops with a jeweled heart on the strap.

Now, a few of the other men chided him about his shoe choice. But, in all fairness at least he participated and even earned a few blisters. Plus, he helped  DVSAC raise more than $11,000.

Way to go Chief, Rome and Pat! On behalf of the ladies at the IFPD, you guys make us proud!