How to Pick out the Perfect Date Shoes

17 12 2012
Take my advice and you won't need to buy bags of shoes for your date.Photo Credit:

Take my advice and you won’t need to buy bags of shoes for your date.
Photo Credit:

Shoes are the punctuation to your outfit. They should say something, and it shouldn’t be, “I wore these for five hours in line for the IPhone 5.” ~ Terri Trespicio of

I think it’s pretty safe to say that most people enjoy the act of dating. You get to go out and do something fun with someone who has at least somewhat peaked your interest. Combine that with the thrill of possibly spending time with someone who makes you laugh constantly or you know, makes you want to tear his clothes off (whatever works for you)… and it’s easy to see why, as messy as it can be sometimes, dating really can be quite fun.

But the lead-up to the date is really where the pressure can begin for a woman. All kinds of questions are going through your mind. “Will he like me? Will I like him? Is this going to be the most boring 2 hours of my life or the most exhilarating 4 hours?” And of course, there’s the all important question: “what outfit do I wear?” Well for me, and many women like me, an equally important question is “what shoes should I wear?”

So in the midst of what many like to call, prime dating season, I’d like to offer up a few questions to consider that will help you decide on the perfect date shoes. They are:

Do I know where we’re going?

This is so important because the shoes that you would wear to a dinner date are not necessarily the shoes you’d wear to go paddle boating or even to a concert. If you do know where you’re going, you must plan accordingly. Sit down dinner shoes can afford to be a little riskier in the heel size, but the last thing you want to do is wear 6-in heels to a date that’s going to include a romantic bike ride through the city.

If you don’t know the details of the date, it’s best to err on the side of caution. I would most likely choose some flats with embellishments on them. These should NOT be flats you would wear to a board meeting. They should be flats that make just as much of  a statement as any heels you would slip on your feet.

Is this a first, second, third, or more date?

Not that you would want to stop trying to dress to impress after so many dates, but this is more so about providing for variety in your wardrobe (which shows the ability to be flexible within yourself). I once went on several dates with a guy and all I ever wore were heels. Sure, I like a good heel, but on most days at work, I wear flats. He never knew that side of me and honestly, it was indicative of the fact that he never got the chance to learn much about me outside of the put-together diva who can strut down the street in 5 in heels with no worries.

Also, it’s helpful to understand the progression in most dates based on the number of dates you’ve already been on. So if you’ve gone on a coffee date, a dinner date, and a museum date, chances are the fourth one might be more active and you should think about dressing the shoes down a bit.

What do I want my shoes to say about me?

I know. Most folks are going to be quick to say that most men don’t care what shoes a woman has on. And technically, that’s probably true. But, if you think he doesn’t notice them and make judgments about you because of that, you haven’t read this blog post before. Here’s a spoiler – men do. We all do.

Can I walk in these?

Oh my gosh. This is so critical. I can’t tell you how many times I’ve seen a woman walking down the street on a date, and I can immediately tell her feet hurt. She’s doing that weird, awkward thing where your arch doesn’t move. And chances are she’s walking reaaaallllly slowly. If I can tell that, the guy she’s with can tell too. And I guarantee you whatever bonus points she thought she got for rocking the come-get-me pumps that night, she lost when she couldn’t walk in them.

Those are the four most important questions I can think of right now. Do you think I’ve missed any?




One response

21 12 2012
Gifts for EVERYONE! « Choices, Voices, and Sole

[…] The perfect date with an amazing guy, in the perfect dress and the perfect shoes, with a perfect […]

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