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Final advice -- girls dig shoes. I mean they REALLY dig them. And not at all just on themselves. I've heard them countless times saying they judge a man by his shoes and that it's a good idea. In all seriousness. It's the kind of "last detail" that proves to some of them that you're "really" classy or rich or hip or whatever the code words are for it these days. (Along with a good belt, to a far lesser extent.)

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I assume you're still talking about black or browm leather shoes? any particular brands I should look out for? Or will just going to nordstroms etc work?

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Believe it or not, lots of women know the brands of men's shoes and some can identify them on sight and really dig a certain few brands as being the best. It wouldn't be a bad idea to ask some women you know what they think.

You could always trust your own judgment, too. In that case, I'd go for a pair or two of shoes first in the same way you build up a wardrobe or shirts -- get a black dress shoe first, as it will go with so many things. Stay away from the browns until you have at least two or three pairs of nice leather shoes, as they are looked down on by a lot of people who don't know better, and at any rate are often thought to work with nothing but browns even by people who seemingly do know better. Brown is a color that asks for an argument from the snobs and self-appointed fashionistas. Get hip and funky with your shoes only after you have a solid base of more ordinary, versatile ones. For you right now, that means at least a couple pairs of black ones, to start.

To me one of the keys of fashion at a non-trashy level is that minimalism is the soul of class. Get shoes that are not too busy or overdecorative. You don't need the ones that have extra big brass or metal on them, someone's initial, etc. When you think flash or style, think of it as a discrete accompaniment to a solid, elegant underpinning, a detail rather than a main attraction. Unfortunately, these can be harder to find than the cheesy glaring fashions meant to sell to your basic pimp. But people who know better, and that includes women, will recognize subtlety in fashion and appreciate it. It definitely puts you a cut above the average joe goober.

Of course, there will always be the occasional idiot you bump into, like someone my friend was dating who said, "I would NEVER go out with a man who wore loafers!" She wasn't kidding either. For her this was actually important.

See what I mean about women having very strong opinions about men's shoes? It can get pretty unreal.

Btw, loafers are fine with most women, and good versatile shoes overall. No matter what you get, there will always be someone who disagrees with it.