Dating Fashion - How to Rock Your High Heels on a Date : Cyber Dating Expert
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Dating Fashion – How to Rock Your High Heels on a Date

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Fashion First Date ShoesDid you know that before every date a woman typically has a pre-date with her closet?

It’s true that women often dress for women instead of men, but our fashion and shoe expert, Hillary Gadsby tells us that despite having hangers filled with clothes, there’s truly nothing to wear out.

“I’m a big believer in the shoes make the girl, and possibly even the date.”

While agonizing over the right top or finding a dress that’s not too short, it’s easy to spend more time with the clothes and less on the shoes and wind up settling on a pair of simple flats instead of high heels. (oops we better toss out the ballet flats on date night).

When it comes to getting dressed, Hillary firmly believes that the look starts at your feet first pick the shoes, then the rest of the outfit will follow. First dates should always include a pair of showstopping stilettos and never flats (save those for a beach date instead.) Whether you?re planning on wearing boots, wedges, or stilettos, here are her tips on how to wear each shoe while still looking fun, fab, and flirty!

If you’re wearing stilettos? aim for a pop of color.

Wearing a classic little black dress to a dinner date? Pair ruby red or metallic gold stilettos with the dress to make it truly stand out! Everyone (including your date, most likely) will be expecting to see conservative shoes that match the dress and it?s always fun to shake it up and include a dash of bold, sexy color with your look.

If you’re wearing wedges? pair ’em with dark wash denim.

Sometimes the first date involves a lot of walking around, like heading to a theme park or music festival, and you’ll want to be able to walk the distance without developing 101 blisters along the way. Sleek wedges are your best bet because the heel is often stacked instead of skinny and can range in size as well. Dark wash denim jeans, a nice blouse, blazer, and a statement necklace when paired with wedges make even the most casual first date also one of the most fashionable.

If you’re wearing boots? include a short skirt.

Find a pair of stiletto thigh-high boots and pair ?em with a short skirt. The boots elongate your legs, giving you an extra boost of confidence. If you still feel self conscious, add a pair of tights which are also super sexy to wear with any of the shoes on my list!

Click here for more first date fashion tips.

Hillary Gadsby is the founder of, where she blogs about what a day in the life of a woman entrepreneur is like as told by her shoes. Find out more about Hillary and her signature pair of bright yellow python pumps at Stiletto Gal’s Facebook page and follow her on Twitter!

Julie Spira is America’s top online dating expert and founder of She creates irresistible profiles for singles on the dating scene. For more online dating advice follow @JulieSpira on Twitter and at


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