One of the most entertaining evenings you can spend in Cayman is at Camana Bay for the “A Walk in Her Shoes” annual event. Why? Because a group of men usually very comfortable in their brogues or sneakers elevate themselves with women’s heels and attempt to maneuver their way down the street for a great cause.

The first time the public beheld this sight, people could not quite believe their eyes. To see the males of the species teetering in some impressive stilettos or wedges was a joy, particularly for women who often wear such instruments of torture.

This year, it will be held on Friday, March 8, at 5:30 p.m. along Market Street in Camana Bay. Gentlemen, get ready to mince!

This fundraiser for the Cayman Islands Crisis Centre hit the ground running, so to speak, in its first year, with crowds gathering to watch the spectacle. Now, it is a firm favorite of the public, particularly when participants go that extra mile (guffaw) to really dress the part.

It is not unheard of to see accountants, bartenders, hotel managers and personal trainers tripping the light fantastic in pretty pumps, flowery dresses, fetching scarves, colorful hats and even a feather boa or two. Have beard, will travel.

Participants can register online as individuals or a team for $25 per person and then get friends and family to sponsor them in their quest.

They must walk a minimum of one lap and a maximum of five. One way to reduce the number of laps they have to negotiate is to raise more money. For every $150 marker they hit, they can cut down their laps by one. So, for example, if someone raises $450, they only have to walk two laps.

The hope is to exceed the goal of $55,000 this year and you can help. Sign up to walk or sponsor a participant and definitely do not miss the spectacle. It is well worth the money.

Some men wear just the shoes, while others go all out with the costumes.

Cayman Islands Crisis Centre

Since 2003, the Cayman Islands Crisis Centre has been helping women and their children create new violence-free lives for themselves. Renovated in 2012 through overwhelming community support, including donations, in-kind gifts, and hours and hours of volunteer time, the center has been transformed into a welcoming place for healing.

With room to shelter 18 women and their children, it is in a secure, private location with on-site 24-hour security.

Visit for more information and for the link to register.

A Walk in Her Shoes has become a major fundraiser for the Cayman Islands Crisis Centre. – Photos: Maggie Jackson

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