Ask Wendy

How Do I Dress for a Date?

Friday, December 9, 2016
Hi Wendy,

What did you wear when you met all those men?  I wear dresses and boots, but I’m not getting many men and I’m not sure if it’s because I’m intimidating them, by the way, I am dressed. Yet I feel more comfortable in a dress and definitely look better.

Holly N. — Irvine, CA

Hey Holly,

There’s nothing intimidating about an article of clothing unless there are spikes coming out of it, in which case, your target audience might be a little more specific. I wore dresses, skirts, boots, and sometimes 6” stripper heels. In other words, I wore what made me happy. Yes, stripper heels made me happy—until they broke my feet and relegated me to the sartorially challenged realm of the orthopedic shoe.

I have a girlfriend who looks sensational in pantsuits. She should not wear dresses, skirts, boots, or stripper heels like me. She should wear pantsuits because she loves them and looks fantastic in them.

Dress to please you. Wear what makes you feel good, attractive, and true to yourself. Be comfortable…well, unless you’re thinking of rocking a red onesie with sparkly white snowflakes—maybe save that for chilly winter mornings at home. If you really need one, though, I’ll lend you mine, but it’s got a short shelf life.

Happy dating!




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