Oh My God Shoes

I received this question a few days ago and have edited it for clarity but not content:

"I'm going to a wedding Saturday and need a new pair of shoes to go with my grey suit pants. Went to DSW and narrowed it down to two pairs of black shoes. Both are very similar, both slip-on leather loafers (no laces, no frills etc), also both are the same price: $65-$69. The question is, what do I get?

Pair #1. Bostonian brand. Ultra-light, flexible, rubber-soled, feels like a cloud on your feet. These are standard dress shoes that I could wear all night and they would be satisfactory.
Pair #2. Italian leather, originally $250, snug, wooden-soled shoe. When I say snug, I don't mean uncomfortable per se, but you can tell its a dress shoe (versus the floating-on-a-cloud Bostonians).

The snob in me is saying, "Get the Italian ones"; they will be stylish and you will look sharp. But the practical side of me says go with the Bostonians. They are still good, no-nonsense shoes, and if I hadn't seen the Italian ones they would be fine. Do I go for Italian leather or exquisite comfort? Also, how much work is a wooden-soled shoe? Am I going to go out one winter and completely ruin them? Does Italian leather stretch?"

Jesus Christ, where the hell do I start?

First, thanks for reading. Let me make a probable correction and tell you that these "wooden-soled" Italian shoes you're talking about are likely leather soles; wooden soles are rare nowadays and are only used in clogs and summer shoes. Also, any leather, Italian or not, will stretch and crease. To negate this, you must polish your shoes regularly and frequently (once a month will usually do just fine) and keep cedar shoe trees in your shoes whenever they're not on your feet. Additionally, don't wear dress shoes out in wintry weather if you can avoid it. I don't care of you spent $1,000 on a pair of leather shoes, they will get jacked up in the snow or rain. Snow boots were invented for a reason.

I haven't seen either shoe so I can't make a proper judgement call, but based on the information you've given me, the Italian loafer is the way to go. There's no difference in current selling price (though you tend to get what you pay for with footwear, and $250 original retail price leads me to believe that the Italian pair are likely higher quality), and while the Bostonians feel like you're walking on a cloud, you said yourself that the Italian pair wasn't uncomfortable, but that "you can tell it's a dress shoe."

And there's the rub. Dress shoes, by definition, have leather soles. That's one of the aesthetic details that sets them apart from their more casual counterparts, which generally have rubber soles. Rubber-soled "dress" shoes are a sartorial oxymoron. Can you get a way with wearing them? Of course, plenty of men do. Will you look polished, elegant, and dapper? Nope. Unless you have some kind of foot injury or are comfortable looking like a 22-year old college grad on his first job interview, all of your dress shoes must have leather soles.

George Frazier, a columnist for Esquire back in the 60's once wrote, "Wanna know if a guy is well-dressed? Look down." The shoes that a man decides to wear will make or break his entire outfit and speak volumes about his sense of style. Assuming proper fit and the like, good shoes will give life to jeans and a white t-shirt, while bad shoes can make a $2,000 suit look like hell. Choose wisely.