I had a friend today ask me about what shoes are best for rainy days. I figured he wouldn’t be the only one who wanted to know so I might as well make a post of it. Most of the time you’ll be more worried about this in a dress situation. If you have on a pair of Chuck Taylors it really doesn’t matter if they get a little wet. Just throw them in the washer and then dry them out later and you’re as good as new.

You can’t do that with your dress shoes. So there are really three different approaches you can take. The first one I don’t really recommend from a sartorial perspective and that is to wear shoe covers. They look silly and they don’t really help prevent rain from getting in up over the tops of your shoes if you accidentally step in a puddle. That being said, if you do want to go this route, go for something bold like these orange covers.

It’s kind of an Agree and Amplify tactic. Essentially you’re acknowledging that yes you are wearing something a little dated and bad, so you might as well advertise it boldly instead of trying to sneak it past everyone without their knowing it.

The next tactic is to have a pair of boots that you wear while you commute and then swap out for your dress shoes when you get to your destination. This only works if you carry a bag to keep your other shoes in, or you have a pair stashed at wherever it is you’re heading so you can pull them on there. I know in larger cities both of these are good options. With something like this you can go the route of a pair of rain-specific boots. Again, I’d recommend the agree and amplify with these. Wear them boldly and don’t apologize.

A pair of rugged boots that are more geared towards the countryside, these guys from LL Bean would do the trick.

Or the option that I would choose if I wanted a specific pair of rain shoes.

These are called Duck Boots and they’re also from LL Bean. They’ve been around forever and they work great as a commuter/rain boot for both business and casual situations. You’re also going to be the only guy around wearing them.

The third and final option is my personal choice. If you live in a climate where rain or snow are fairly normal, I recommend getting a pair of dress boots. With something like this, you can wear them all day without worrying about changing anything. They fit in perfectly with a suit and tie but are also a great way to dress up your casual clothes for the High/Low look you want. If you want dress boots that are good in the rain, the leather you want is called Shell Cordovan. It’s a thick leather that’s naturally rain resistant. Also, go with a dark color. It looks better against the wet concrete and doesn’t show water spots as much.

Good dress boots will run you quite a bit of money but are worth the price. However, if you don’t want to shell out a ton of cash, you can sacrifice a bit in quality for something like these from Urban Outfitters. They won’t protect you if you’re ankle deep in a puddle, but should be fine for regular traipsing outside on a soggy day.