Women loooooove shoes. We do! And what is one of the first things we look at when we see our date approaching? Yep! Shoes. Why? Because your shoes can say so much about you: Whether you are high maintenance or laid back. Whether you are doing well in your business or not. Whether you take care of yourself or have a take a more laissez-faire approach. All of these perceptions come from the floor up – it’s all in your shoes.

Details, Details, Details

Before we even get into what shoes every man should own, it’s important to do some “housekeeping,” if you will. Your shoe upkeep is just as important, if not more than the actual shoes you are wearing.  When you take care of your shoes, which seems to be a relatively minor detail, it is then assumed you take care of the other details in your life as well. {Read: You take the time to take care of your shoes?  You probably take more time to take care of your girlfriend. That’s a dating brownie point.} Shine them, wash them, get the soles fixed if needed and even change the laces! Here’s a bonus tip: Choose a bold color with your casual kicks for a subtle impression of creativity!

Don’t be “Dated” when Dating

This other bit of housekeeping is also important. You can shine up an old shoe, but if the styling is outdated, then that is a strong indication of your status at work, your level of awareness, and your knowledge of your current and contemporary surroundings. So if you find anything on the following list in your closet, put them aside until you replace them. Once replaced, it’s time to let go!

  • Clunky, square-toed shoes
  • Clunky and wide shoes with round toes
  • Thick and wide, white (and/or dirty) tennis shoes
  • Overly detailed shoes: anything with contrast stitching or too much hardware
  • The over-extended, sleek-point-toe loafer or lace up (AKA the sleaze)

Getting on Trend

Now, let’s get into the shoes – and I am not talking about “trendy” shoes.  I’m talking about contemporary shoes. No matter what the shoe, whether it’s a tennis kick or a dressy loafer, shoes are being designed for a slimmer fit (just like the current style of men’s wardrobe fits, which will be a story for another day). A slimmer shoe actually can make you look slimmer overall, as well as make you appear taller when worn with a pant of similar coloration. Yep. Slimmer and taller. Which is why having your shoes updated to the newer styles is important for your dating life.

The Dating Shoe Staples

So with all of this in mind, let’s get you covered on the must-have shoes for date night, and how to incorporate them into your wardrobe.

  • Grey Oxfords – A new and contemporary shoe staple to add into the mix of your dating wardrobe. Great for day dates and evening dates, they pair perfectly with light to medium denim, greys, khaki’s and whites. Just remember to wear a light slim sock!
  • Medium Brown Wing Tips – The hip and more stylish replacement for the obligatory black dress shoe. The Wing tip is creative and detailed, while mixing well with light and dark gray slacks, navy slacks, and medium to medium dark denim.
  • Black Loafer – Note that they are called the “take me home” (love that!). This is perfect for a dressier date, fancy dinner, and/or dancing. Worn with your suit is an obvious use, but for a laid back dressy approach, try pairing your black loafer with your dark denim, button down and a blazer. Here’s an extra style tip: Untuck your shirt and leave the bottom button undone for a more relaxed feel which will show your date a quiet, yet cool confidence.
  • Dressy Sneaks – These hip new kicks are a perfect update to every look when you want to appear updated, yet understated. Pair these with dark and medium denims, or get creative and try them with a dress pant and hip graphic tee.
  • The Updated Chuck – This is a fresher way to wear your casual kicks. The leather style gives off a luxurious feel to your day gear and sends the message that quality matters. Great for bikes rides, long walks and ice cream trips!

So, get your shoes whipped into shape because a wise shoe choice will always send a confident message to your date.

Named “LA’s go-to stylist” by the Los Angeles Times in 2012, certified image consultant and personal stylist, Laurie Brucker of LaurieBstyle LLC, is the stylist for real people. With a degree in Apparel Merchandising from Indiana University and a certification from the Fashion Institute of Technology in New York City for Image Consulting, Laurie was hand-picked as a top stylist in 2011 to represent Stacy London from TLC’s “What Not to Wear.” Keeping style very personal, Laurie has developed the “Style Strategies for Success,” which empowers her clients with the tools, techniques and art of creating your own unique sense of style that’s right for you!
  1. i dont know any men that would take the time to read this article although i agree with everything you said. i find guy either dress well or they don’t. a lot of the older guys for some reason, dress like they are stuck in the 80’s. its such a turnoff. it the bad shoes, the bad jeans, the bad hair and the mustache.

  2. I had seen some of the gray oxfords. Thanks for the advice!!


  3. Let’s be honest… If a woman like you, it’s not going to matter what type of shoes you’re wearing. Also, if a guy is that much into his shoes, the woman is not going to be that much into you. “Clunky squared toed shoes, wing tips, Oxfords”? I have no idea what these are”. I’ve never been out with a lady and afterward she said, “boy, that guy Seth was so cool… too bad his shoes were so lame!”

    And I totally agree with Linda… The only reason I read the article was because I thought it Sounded so funny. However, I do think confidence is always the key… And if dressing well is going to make someone feel better about themselves and give them confidence, then in the long run that is what will work.

  4. The links don’t work, but that may just be my computer. While I think there is something to be said about being well dressed and reasonably fashionable, I would nonetheless hope that people are a little more forgiving than that. There is more to life than shoes, or what people will tell themselves that the shoes represent.

  5. For the detractors of this article,… a woman told me that she appreciated that I showed up to a date with an ironed shirt. She said that I’d be amazed at how many men are just slobs. Guys: just because a woman doesn’t call you a slob because of the way you dress doesn’t mean that she isn’t thinking it.

    Men want women who know how to dress up, look good, have great hair and wear the little black dress. If you don’t think women want the same: A man that they can be proud to be with and that is well groomed along with all his other qualities, you are mistaken. If you’re not getting to date the women that you want, look in the mirror. Appearance matters. Its not shallow as some have suggested. Its chemistry and sex appeal.

  6. Hi Everyone! What amazing comments and thank you all for dropping in with your shoe thoughts!

    Seth, I have to say you are absolutely correct, what do these shoe names actually mean to you? Men are typically not as visual and detailed when it comes to shoes as women are, so I can completely understand that this story doesn’t make much sense to you. But, confidence is key and I appreciate that you have pointed that out as well.

    When it comes to shoes, I am speaking from a contemporary standpoint. In this day and age, because of the internet there is a very heightened awareness to style, quality, shape and image. And this shoe ‘ideal” is a riff from an expert on that. Are all men going to comply? Absolutely not. Are all women going to agree with me? Absolutely not. The beautiful thing about style is: that we are the style, and if we are confident, we will make everyone believe we have the style. I have this saying: If you believe, then I will believe. Meaning if you believe in yourself, then I will believe in you too knowing nothing about you. Confidence is everything. And when it comes down to it, your first impression is everything. So if dressing in a more laid back way is your thing, then the girl who you are looking for will love you for it.

    If you have stories you’d like to hear, or style questions you want answered just email me and I can incorporate them into my next stories for you.

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