OMG shoes.

Dr. Sunday,

Simple one for you, I'm looking into a new pair of shoes; something classy yet able to be beaten on. I was first thinking those semi-boot shoes, well I think of them as such. Always shied away from them really. So I think more like a high top dress shoe. What is you thought on stylish shoes for men?

Fuddled over Fashion

Dear Fuddled,

This is indeed an easy question. Speaking strictly from a personal standpoint, my tastes in footwear for men are as much based on functional utility as they are on style. The ideal footwear in a man's closet should be as follows: Something casual, for daily wear, particularly outside of the office, but something that can be utilized in a multitude of circumstances (in my case, a pair of Diesel trainers, or my low-top Converse). Something "worn-in" or "get-dirty" appropriate is also key, typically something you've retired from daily, public use (I have a pair of Vans prison-issue velcro shoes, for running outside really quick; an elderly pair of Chucks, for when I know I'll get muddy/dirty/grass-stained/etc; and a beaten to hell and back pair of Vans low-top skate shoes, for when I know I'm going to get splattered in paint or things of that nature). A pair of boots is vital, as is something dressy-- of course, the clever and dapper young man can combine these two pieces in any number of ways to the greatest possible effect.

To give you an idea, and bear in mind, I receive absolutely no compensation for any products I mention by name, I own one pair of dress shoes. They are basic black loafers, of a brand I can't even name. I am pretty sure I inherited them from my dad when I had to go a dance in high school, or when someone died. I never wear them, because they are old man shoes-- and not in that fun and quirky vintage "old man" style, they're merely outmoded and pointless. When I need to have my feet dressier, I take the opportunity to make myself presentable while still maintaining my personal style.

I own two pairs of boots, which serve, variously, in the offices of dress footwear as well. They are stylish and functional, simple and utilitarian, yet they state by context that I am no mere office lackey or pencil-pushing d-bag. Pair of boots number one, of course, is my precious and well-loved Dr Martens. They're black, steel-toed, and rise well enough above the ankle that I could wear them without fear that I will be mistaken for the kind of person who voluntarily owns a hackey-sack, but also not so high that I might be mistaken for the kind of person who has questionable piercings in even more dubious locations on my body. They are simple, which is key, yet I keep them well-polished enough to wear under even basic slacks to the office, while still being able to wear them on the streets, under jeans, while presumably spoiling for some sort of fisticuffs, I don't know. They're perfect, and moreso, they came to me as a gift from my lady love, so I feel even better about wearing them.

The second pair of boots, I also utilize, even more regularly than the Docs, as dress footwear. These are a pair of basic black "engineer boots." No laces, just a chrome buckle off to the side. I've removed the brand tags so long ago that the name eludes me, but I've owned these boots for over a decade. They, too, are steel-toed, which I find useful on a number of levels, and typically earn me compliments as they are an unexpected yet flattering addition even to my more professional wardrobe. Of course, I've also regularly worn them onstage, as wicked and imposing accessories to my already sometimes sinister aspect. Frye makes a decent version of these in a more fashion-oriented context, though I acquired mine literally from a store specializing in work-footwear. They rise to just below midcalf, and absolutely kick ass.

While I don't suggest you copy my suggestions directly, I will state that the important message here is not to necessarily purchase as I have purchased, but rather to consider multi-functional utility, and to always remember, in building personal style, regardless of your venue, that true STYLE, whether for a man or woman, comes from making it YOUR OWN, rather than following some idea of what is fashionable or trendy. It's not about fitting in with your culture, subculture, or the magazines you read-- it's about being yourself, no matter what, and making sure the essence of who you are is represented in everything that you do, and indeed even to the shoes on your feet.

I hope this helps. Best of luck shopping.
Always Listening,
Dr. Sunday