Waterproof overshoes: am I using them right?

I've got a couple of pairs, and have had similar experiences.

The best I can do is with my better pair (with a reasonably tight but comfortable ankle strap) underneath my splash - resistant leg warmers. That keeps out a short heavy shower, or light drizzle for a few hours, but persistent rain always gets in (and anyway feet get sweaty in overshoes). Short socks (well below the ankle band) help as they don't provide a part for water to wick.

They'll never seal well enough if your feet dip in a puddle, even if, like me in winter, you tape up any vents in your soles. Even splashing from underneath can get in eventually.

The overshoes are still very beneficial in cold wet weather, as the water in there is much warmer than the rain, and wind chill is reduced. In warm weather I often don't use them (e.g. Saturday I was riding all day, mostly in rain, but would have been too hot with overshoes).

I only cycle in waterproof trousers well below freezing, as a third windproof layer over bike tights and running leggings. Even breathable ones are too hot and get very sweaty. In fact, in summer rain I'm reluctant to wear any form of jacket. Breathable ones are too warm and aren't breathable enough, so I carry something thin and light, but end up just as wet from sweat.

Overshoes over the top of normal bicycling shoes with cleats are not "waterproof". Water gets in through the cleat holes. And, as you've discovered, through the ankle holes.

All you can do is minimize the amount of water that gets into your shoes and delay how long it takes before you're soaked.

First, if you're going to use shoes with cleats, you need shoes that are specially designed to have waterproof cleat holes. These are usually sold as "winter cycling boots" or similar. Otherwise, water works its way in through the cleat holes.

Second, as you've already discovered, you need to put your tights/rain pants over the tops of the shoes. If you don't water will run down your legs right into your shoes and rapidly fill your shoes so that every pedal stroke squirts water out.

Third, you need a good front fender with a spray flap. Your front tire throws up a lot of spray - much of which goes right onto your feet and lower legs along with right into your cleat holes. It WILL work its way into your shoes and soak your feet quite rapidly. So stop as much of it as you can with a fender that has a good spray flap.

And after all that, if you ride in a solid rain you'll be lucky to get an hour into your ride before your feet are soaked anyway.

Also, truly waterproof pants don't breathe at all. So any sweat from your legs won't evaporate. If you're riding hard and/or long enough you'll wind up soaked anyway. And pants or tights that do breathe will let some water through.

Been there, done that.

As other answers have said, water will always get into your shoes. If this is a problem for you, then the best answer is to not care about it!

In warm weather, you might simply not wear socks, and your bare feet will sort themselves out. The biggest problem for wet feet is socks holding cold water next to your skin. In the extreme case, sandals with cleats exist - of course you would need to be sure your toes weren't going to contact the ground, so not ideal for trails, but you get the idea.

If bare feet aren't acceptable, waterproof socks are the best alternative. The best known brand is probably Sealskinz, at least in the UK, but others are available. The downside here, of course, is that they keep the sweat in as well as the rain out, so you need to be pretty scrupulous about your foot hygiene and about keeping the inside of the socks clean.