Menswear Monday: A 5 Shoe Closet

As guys, we're fortunate that our shoe situation is a lot more simple than our lady friends'.  Shoes for us break down broadly into the categories of dressy and casual, and for many of us, that's as far as we generally think about it.  But as we face a range of different social situations and events, it's easy to be left wondering what the best shoe is for that particular occasion.  With a carefully curated collection of shoes, you'll have all your bases covered without turning into some chick from Sex and The City. Here are the five shoes that every guy should have in his closet:

1. The black dress shoes.  The label "dressy" isn't really descriptive, and it runs a pretty wide range.  If you're thinking of it as a spectrum, these will be your most dressy shoes.  They'll go with your dark suit for more formal events like weddings and funerals, and can work at a more dressed-up office, too.  Go with something conservative, not flashy or trendy, like these cap-toe oxfords from Kenneth Cole.

For: getting dressed all the way up

Spend: The most of any of your shoes.  Whatever your personal limit is, spend it here.

2. The brown loafers. If you're somewhat advanced in your thinking about dressy shoes, you know that you need brown and black shoes, so here are your browns.  They're more casual, to go with khakis, or when you're dressing down a suit.  They can also be used to dress up jeans on a date night, and once they're well worn-in and beat up, they can go with just about anything.  (If they are really beat up, keep them, but buy a new pair for the dressier occasions.)  For these, get the classic (and very affordable) Bass Weejuns, a moccasin-style loafer that's been a preppy staple for decades.

For: Anything that, in the back of your head, you know you shouldn't wear sneakers to.

Spend: No more than a hundred bucks.

3.  The boots. You'll also need something a little more rugged, that you can beat up on, that will be your go-to shoe to wear with jeans.  This will be the first chance to get personal with your style: if you're feeling kinda preppy, go with a chukka boot version of the classic Sperry Top-Sider; if you're more outdoorsy, grab some Red Wings or Timberlands; or if you just want something that goes with everything, look no further than Clarks Desert Boots.  Whatever you find works for you, wear it, resole it, wear it again, and repeat until they're the shoes you love the most.

For: Man stuff

Spend: Relative to the amount of man stuff you do.  If you're in negotiations for your own show on TLC, maybe spend more than for the black dress shoes.  Otherwise, keep it cheaper.

4. The sneakers.  It's Saturday, and you're running errands all day.  You need something comfortable that goes with shorts, that you don't have to think about.  Oh yeah: and they should be cheap enough that you don't care if you spill barbecue sauce, motor oil, or bacon grease on them.  Enter the Adidas Samba.  Yeah, they're soccer shoes, technically, but they're classic and go with anything.  Get them in the classic black-and-white color combo, or find one of the many different varieties Adidas offers now.

For: banging around, slipping on at a moment's notice.

Spend: Your cheapest shoes.  Find something on sale and just grab it.

5.  The Wild Card.  This is your best opportunity to show your personal style.  This shoe can fall into one of the other categories in a broad sense, or be something completely different.  The point is, they're very much about YOU.  As guys, we don't often do the "jumping up and down squealing" thing when we go shopping, but if you find a pair of shoes that makes you stop in your tracks and go back for a second look, get them.  And put them in this role.  For me, it's my white buckskin oxfords that I got for $8 at a garage sale, and then nursed back to health.  For you it could be another pair of boots, a dressy pair of sandals, some high-end Nike Dunk SB's, or some crazy brogued wingtips.  Go crazy, in your own way.

For: whatever you want.

Spend: whatever you want.

With these five shoes in tow, you'll be ready for any occasion, matching any outfit, and looking like you put in a ton of effort, even if you didn't.  And that's the whole point, right?

-Rob Hays