Buying Fashionable Men's Shoes - 3 Tips to Find Great Dress Shoes

So you've bought that great suit, had it tailored perfectly, bought some slim fit shirts (as discussed in this post Buying a Slim Fit Shirt) and now you are wearing a pair of clunky, square-toed shoes you found at Payless.  Shame on you!  Once you've got a tailored look, you need to translate that across your entire wardrobe.  Shoes are the anchor of your style and need to reflect the choices you've made in the other elements of your look.  Today I'd like to talk about some basics you should know before you go out and find your next pair of dress shoes. I'll be comparing what you should and should not do as well as how to keep your footwear fashionable by buying classic looks.

Shoe Soles: Go Slim, Go Leather.

Chunky, square-toed shoes were in style for a while but that fashion has (finally) gone away.  When shopping for your next pair of dress shoes, check out the soles.  They should not extend out too far from the shoe and should not be too thick.  Also, invest in a pair of shoes with leather soles.  There is a common misconception that rubber soled shoes are more comfortable, however leather will breathe more and if the leather sole is too slippery, simply score it with a knife.  Below you can see the difference between a shoe with soles that are too large and rubber compared with a classic slim profile shoe with a leather sole.  The shoes on the right can be found at Brooks Brothers.

Lace-up Oxfords: The Style You Need First

There's no way around it, if you want one pair of great shoes that will work in almost any setting the lace-up oxford is your only choice.  Luckily there are many variations that you can choose from:  wingtips, cap toe, plain toe and so on.  Though black shoes are a staple, if you are just starting your shoe collection I would recommend going with a brown shoe first.  They will go with almost any suit you have besides black (which should not be one of your first suit colors, see why navy should be your first choice in this article on Navy Suits.)  Dark brown will be a bit more versatile but you can go for something lighter if you want a shoe that will make a statement.  Below are two great examples of brown shoes, both dark and light, that are a great beginning to any man's shoe collection.  The wingtips on the left can be found at To Boot New York, while the cap toes on the right can be found at Maganni.

Sticker Shock: Calm down, it's going to be ok

If you're like most men out there, you're probably going to have to take a moment to calm down and regroup once you see the price on a pair of quality made, leather soled shoes. Let's take a moment and take about being penny wise but dollar foolish. Think about the last time you bought a pair of $30 dress shoes. How often did you wear them? How long did they last before they were uncomfortable or had worn through?  The longest you can expect a pair of shoes like that to last is 6 months if you wear them even moderately often.  So let's look at the cost of those shoes over 5 years, by the end of that time you would've paid $300 for 10 pairs of uncomfortable, ugly shoes. Rather, if you spend that money upfront on a pair of well made shoes they will not only last you longer than 5 years and you will look great the whole time. Not to mention that your feet will be more comfortable and your back will probably have less strain on it.  So take some time and invest into some well made shoes that will last years rather than months on your next purchase.  While you're at it, check out this dapper pair of shoes from Allen Edmonds.  The clean lines on these are such a classic example of timeless style.

So now you're ready to buy some fashionable, well made shoes that will last for years.  Don't forget that you need to look at material labels on shoes to determine exactly what they are made of, many shoe store associates will tell you that you are buying a leather shoe when it is actually a leather blend which will not last nearly as long.  Do you already own some great shoes?  Let me know where you got them and post some pictures, I'd love to see them.

Thanks for reading.  As always, be dapper.