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Edited by on June 23 2010 at 12:58 PM

Dating columnist and shopping addict, Carly Spindel has dated her share of men in NYC. For every type of date, there’s a different type of outfit. Here she takes us into her closet to handle a little problem, what should a fashionable girl wear when dating a short man?

What To Wear When Dating a Shortie?

I’m 5’2” and I’ve always considered myself a shopping whore. I could spend all day looking for new shoes and clothes. When I was a little girl, I couldn’t wait to grow up and have a boyfriend to dress up for. Well, now I’m all grown up but I’m boyfriendless. I go on a crazy amount of dates, so fortunately for me, I live in awesome dresses and even better shoes.

As part of my job, I go on dates with all different types of men. I’ve met some nice guys, arrogant ones, tall men, and of course, short ones. Being that I’m quite tiny myself, I don’t mind dating men who are only a little bit taller than me. Luckily, the way men come in all different shapes and sizes, so do shoes and dresses.

The Shoes

The first time I went on a date with a man who was 5’8, I had no idea what to wear. I panicked for a few minutes and then calmed myself down. All of my shoes are at least 5 inches tall and I thought it might make my date feel bad if I was almost his height. So, I did a little research and found a few pairs of not so high heels.

My shoe obsession of the moment happens to be a pair of turquoise flat sandals from Elizabeth and James Blaze Flat Thongs.

What To Wear When Dating a Shortie?

They’re colorful and simple. Turquoise goes with everything, including short men, which is why these shoes rock. So, if you’re going on a date with a man who’s almost as tall as you, I suggest wearing these turquoise beauties.

They’re $175 at

If you’re like Victoria Beckham and you aren’t comfortable in totally flat shoes, opt for a heel, but a very low heel. This gives you the chance to still feel sexy, while making sure not to tower over your date. I know that women feel sexier when they have on a pair of extremely high heels. But if your date is a cutie, give him a chance to feel like a real man. Let him appear tall.

In order to do that, I recommend my newest shoe crush. These Sergio Rossi stilettos are sexy and on sale!  (Grab them on for only $455)

What To Wear When Dating a Shortie?

They’re also feminine and very unique. So when your date takes you to an over crowded bar, the girl sitting next to you won’t be wearing the same shoes.

Now that you have the shoes covered, you just have to figure out what to wear with them. I’m sure your date would love it if you arrived naked, but that’s not appropriate so I recommend wearing a dress.


I’m a native New Yorker so I live in black. Head to toe I’m usually dressed in black, even down to my bra and underwear. Black is sexy, slimming, and elegant. One dress I die for is by Rag & Bone. It’s tight and short so it works perfectly with flats. $395 on

What To Wear When Dating a Shortie?

I’m a huge fan of mini dresses, but if you wear them with high heels, you can look a little slutty. That’s why whenever I go out with a short man, I put on a really little dress and embrace a comfy pair of flats.

However, not everyone likes blatantly sexy clothing. So, if tight and body hugging dresses aren’t your thing, I recommend wearing a flirty, fun dress on a date. They’re still sexy, but in a more understated way. Rebecca Taylor makes great dresses that are super romantic. This one looks good on everyone and it’s even a fun color. Available on for $275.

What To Wear When Dating a Shortie?

I bet you had no idea that a whole new wardrobe can come out of dating a short man.

Instead of being afraid of dating someone who might be the same height as you, go out and buy a flats-appropriate dress and matching pair of shoes. You might enjoy the date. And even if you don’t, at least you scored a few new items for the summer.

For more from Carly Spindel check out Carly’s Dating Chronicles.

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Story by Carly Spindel

Carly Spindel is a hopeless romantic. She has a dating blog where she chronicles her dating life. She is a native New Yorker and loves to people watch. If you see her on the street, she will most likely be wearing oversized sunglasses and looking for her next boyfriend.