The Shoes Can Win or Lose! What she looks at when she checks you out.

Most girls I have noticed checking me out usually start from the feet up. As much as I would love to imagine they are checking out my size 13 shoes with lust on their mind, the reality is, they are looking at what is on the feet more than anything. From unscientific research I have determined that shoes tell a woman a lot about a man. Why not say something with them beyond that you need additional arch support?

The place to start is type. I am going to focus on the dressier style, because that is what I do. Gym shoes are strictly a utility for me, that said, if you want my input on them, go new balance and go simple. Green and purple don’t go with anything, unless you are the Joker or Lex Luthor. I travel a lot so I go with loafers, easy to take on and off, comfortable, they look good in jeans, suits (single breasted) and khakis. I am a fan of loafers with a bit or plain front venetian style . Both of these would look fantastic in all situations.  For an even more casual look like a sportier slip-on or a Moccasin style. They of course work best with blue jeans or a darker colored casual pant.

Lace ups are best with a suit. My personal favorites in this style are square, cap-toed shoes. Cap toes bring out the shine in the shoe a bit better and are actually easier to shine. I like square toed shoes and I will explain why further down. Wingtips… save those for the pinstripe suits, Gordon Gekko. Saddles are a great casual option. For my height and build, I think square toes help accent my build. Most shoe stores have mirrors, bring a lady-friend with you and use the mirror. How the toe looks will make a difference in your line. See, Brown..

Now that we have covered some styles, we should talk about color. What colors should you mostly look at? Here is a list in order of importance: Brown, Brown, Brown, Reddish BrownBurgundy, Brown again, Black and then some other colors. For some reason people think Black is the best color for everything. The uneducated (and those who think they are) will try to sell me on the merits of owning a black suit. I am not a mortician, a Limo driver or host of a restaurant, I digress, that is for a different conversation. The same mentality applies to shoes. It is a sick lie perpetuated to you by the liberal media or some malicious fashion designer with entirely too much control and time on his/her hands. Brown shoes work best with every color pant out there save for black (but that is why you get the red brown or burgundy) even then you can pull it off with the right shirt.

If you are wearing a blue, grey, brown, white/cream based suit or pants, brown is the way to go. So if you don’t want to own a ton of shoes like me and have people wonder about you when they glance in your closet, getting a good, versatile pair of brown dress loafers or some casual oxfords can save you 3 pairs of dress shoes. The other pair can be black (for the record, black shoes only, really go with black and grey based suits/pants and blue jeans, barely) lace-ups for formal events and then you can lounge around in your NBs or Nike self lacing shoes the rest of the time.

Now we have the style and color chosen, lets talk about soles. Everyone needs a good sole (except maybe Gingers, I am told) and I am going to go against what most shoe manufacturers will suggest. Get leather soles. If you are going to spend the money on a good pair of dress shoes (and you should, the payless ones really don’t wear well, trust me the extra money is worth it) stick with shoes that have leather soles if you can. “Single guy, why would I want to do that?!” you ask, there are several reasons. First, the quality in making the leather sole is far more thoughtful. You can more easily get the soles repaired properly (not have a shoe maker slap napalm like plastic on the bottom of your shoes with rubber soles). It is more versatile in everyday life, the only time I see you at a disadvantage is if you were being chased by a Velociraptor. They are also comfortable and better for your feet. Recent studies and shifts in running shoe trends show that all that stuff we made to cushion our feetsies are probably bad for us. The playability of leather soles really is better for walking. Lastly, you can dance in them (did that guy just say dance?) as well as conduct an interview in them. We will address the dancing thing in another article.

You may have noticed that all of the links are to Johnston and Murphy. While I do own some of their shoes, I am mostly using them as a visual source. If they don’t like it they can give me a cut of the free advertising. We should talk about where to look. If you are one of those hateful people who have shoe sizes between 7-10, you can go almost anywhere and get discounted quality shoes. You middle of the road rapscallions get access to plenty of fine grade shoes through overstock websites and some of the finer shoe makers  even have refurbished shoes. Go out and look now, me and the other big guys will wait…..

Are they gone? Good, guys who have more sizable feet, let’s talk. I know it sucks getting shoes at reasonable prices, plus those bastards at the store always seem to stock our size at the bottom of the rack, make the big guy bend over. You will not likely find shoes in an 11 or higher on discount from AE or JM. You might luck out in an outlet store and even then you have a limited selection. My suggestion, if you want to really make a statement with your shoes is to check out Stacy Adams. SA is a little bit more urban and certainly more flashy than AE is but the wonder about them is that they lean to the larger sizes. I don’t think JM makes anything in a size 15… I have seen them with Stacy Adams. Don’t even walk into an Aldo shoe store if you are larger than a 12.


So there is your start. As we continue this journey in fashion and discovering your own style, I hope you will start to pick up some ideas on how to make what you are wearing accent who you are. While we have labeled this Fashion, I want to stress that what I am hoping to inspire in this is some style. Fashions come and go. Skinny ties were the rage when I was 10, now they are back in my 30s, next I will see flat bottom ties and adults wearing looney toons themed ones. Style never goes out as long as it is you. While I do make suggestions and will sometimes throw out edicts (especially about suits) I certainly want you to take the information and then apply it to you. To paraphrase my one friend’s favorite statement when he is teaching. Don’t dress like me… dress LIKE me. So as long as I am allowed to on this website, I hope to help you express yourself, wear your clothes with confidence instead of them just being cloth that covers you up.


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About the Author: Tom is a director of IT for a financial start-up. He spends his days designing infrastructure and supporting high net worth advisers and their clients. Traveling much for work affords him a great perspective on life and what is important. The high travel has ensured that he goes on a lot of first and second dates.

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  1. Paul says:

    Dude, guys with big feet have the RUN of shoes at DSW.  Variety of styles to choose, and usually with sizable markdowns.  And again, for some reason, they’ve got millions of shoes in double-digit sizes.

  2. Damon Stone says:

    I’m going to disagree with your color scheme Tom. A pair of Dark Brown shoes and a pair of Black shoes will get a man through life just fine. I don’t want to be just fine, and I know you don’t also, but for people who can’t figure out that they should be wearing nice shoes to begin with, I say go with the infinitely adaptable dark brown and black and it will go with 90% of everything in your closet.

    • The Single Guy says:

      I would say a red brown shoe can replace the med and black shoe. The red tones will work with black and grey colors. Many of the shoes linked were on the darker side of brown.

  3. L-Train says:

    This sounds like, Queer Eye for the Straight Guy…. but written by a straight guy???