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As part of my "in case it rains" gear, I have waterproof jacket, waterproof trousers and waterproof overshoes.

The first time I used them I had the "brilliant" idea to tuck the trousers into the overshoes, with the result of pouring all the rainwater directly into my shoes. What a miserable day it was.

Last time, remembering the previous experience, I have fastened the trousers Velcro straps around the overshoes making sure that the overshoes were under the trousers. At the end of the rainy day my socks, shoes and feet were nevertheless drenched in water.

Am I missing something in the way I should use overshoes, or is it simply unrealistic to have really waterproof overshoes?

I use cleats, leather mountain-bike shoes and when the above happened I rode about 6 hours, the first 4 under the rain, on mostly paved roads and some white roads.

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    I’ve only ever heard of overshoes being unable to keep water out. I’ve never heard of anyone who managed a 100% waterproof seal. Just accept that you’ll get wet when it rains (I’d even discard the waterproof trousers). I’ve discovered that watertight socks are great (because they are light and compact) but they have the same problem with water coming in from the top (maybe not an issue if you have waterproof trousers). – Michael Aug 19 '20 at 10:08
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    Are you riding hard and putting in effort? I find anything above a casual dawdle leaves my sweat inside the pants/jacket. IE are you wet from rain or wet from sweat ? – Criggie Aug 19 '20 at 10:57
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    Also - do your overshoes have holes in the sole for the cleats to connect with the pedal ? – Criggie Aug 19 '20 at 10:58
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    @Criggie may be a case of 100% waterproof won't let a drop of sweat out ! – mikes Aug 19 '20 at 11:56
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    I think it's unrealistic to expect your feet to stay dry while cycling with overshoes on when it rains, because you sweat. The overshoes are designed to keep your feet warmer when it rains, by reducing the amount of water pouring through your shoes, and by protecting your feet from the wind to reduce wind chill. – rclocher3 Aug 19 '20 at 14:01
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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.

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    It sounds like you're a member of the special club mentioned in Rule #9! – rclocher3 Aug 19 '20 at 14:12
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    @rclocher3 I'd like to think that's true, but it's more that I live in the UK, and like to get the distance in. The law of averages says I'm getting wet. Though perhaps earning a badge for a 200km ride in each of 12 consecutive calendar months is worthy of rule 9 – Chris H Aug 19 '20 at 14:20
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    Surely the proportion of riders that are in the special club is higher in the UK, but I think the rule should be taken literally: if you ride in weather like that on purpose, then you're a member. After all, surely many people in the UK don't ride voluntarily when the weather turns foul. – rclocher3 Aug 19 '20 at 14:28
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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.

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    "Truely Waterproof pants don't breath" is incorrect. Breathable allow water vapour to pass though, water proof fabics blocking water in its liquid state. There are many example of breathable water proof fabrics. What does stop breathable fabrics working is then the DWR get saturated and there is a layer of water on the outside of the barrier membrane, or the outside humidity is 100% and water vapour cannot pass though the barrier. That said - products that remain water proof and breathable after hours of heavy rain are not cheap, and even the most expensive have limitations. – mattnz Aug 20 '20 at 2:02
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    @mattnz : True! Vapour passing through breathable is a nice marketing stunt and works in low sweat producing activity, such as moderate walking. I've had several of these rain jackets and even with those from reputable brands are unable to leave you dry underneath. Which is understandable because with the outside air saturated with humidity, the humidity inside the jacket will also reach 100%. Physics! – Carel Aug 20 '20 at 9:54
  • If you've only got summer (or unspecified) cycling shoes, it's often possible to take out the footbed and put duct tape over the cleat holes and any sole vents, on the inside. This may completely stop water getting in from underneath, but it will certainly reduce ingress that way to far less than you get from above. – Chris H Aug 20 '20 at 11:10
  • A mudflap that reaches almost to the ground can be made from a length of old inner tube. Slit open and fold over 1-2 cm at one end, gluing with contact adhesive (or patch cement if that's all you've got). That's the bottom, trim the top to whatever shape you like and pop-rivet it to the mudguard. – Chris H Aug 20 '20 at 12:30
  • @mattnz you're theoretically correct - but in practice Andrew's statements about breathibility are more realistic. There are a few options to provide some protection without completely enclosing the legs, such as capes or rainlegs (like shorter varieties of horse-riders' chaps), but no real equivalent of the vents on jackets that help the breathable membrane (and help keep the wearer cooler in the first place). – Chris H Aug 20 '20 at 12:37
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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.

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    Traditional wool makes an excellent winter sock, still warmish when wet. If a thinner sock is needed, wools like Merino and Angora work well. – Criggie Aug 19 '20 at 22:31
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    Overshoes are best to keep the cold off. By adding an extra layer of air they can provide protection against wind chill even when wet. In the way the thin layer of warmer water inside a wet-suit protects the diver against the cold water he's in. – Carel Aug 20 '20 at 10:02
  • Water running down the legs will end up in the shoes and on the socks. – Carel Aug 20 '20 at 10:07
  • @Carel That's not a major problem if you've got waterproof trousers. And the idea with the socks is that they get wet on the outside and you stay dry on the inside. – Graham Aug 20 '20 at 19:58

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