Shoes for sightseeing in May?

I am usually walking as well as touring so I usually have my water proof hiking boots plus a pair of nice leather shoes. I love Finn Comforts, but they are very pricy. I think that spraying your shoes with silicon prior to the trip and having a second pair helps. I know it's takes up space, but they can dry out if you get into one of those down pours and all day rains, but you still want to tour. In the summer I bring a pair of sandals as well with me.

I tend not to take an umbrella with me in the UK for touring as you should carry it every day. I prefer a rain jacket with a hood.

Pam

I have traveled in Scotland in May the past 2 years and worn boots all day every day. A pair of knee-high flat-heeled leather fashion boots (the kind you can tuck your jeans into and also wear with a dress and tights) worked great. Spray copiously with silicone waterproofing before leaving home.

It will rain, and an umbrella won't often help because of the wind. Temperatures in May are unlikely to hit anything above 60 to 65 F, especially in the more northerly highlands & isles, so you don't have to worry about being too warm.

Form follows function and style is in the eye of the beholder. With that said, if you want to try to keep your feet dry, use light hiking boots with a build in breathable waterproof (e.g. Gore-Tex) membrane liner treated with surface water repellent treatment (e.g. Nikwax) and wear merino wool socks (e.g. Smartwool) of the proper thickness.

My preference is a breathable waterproof rain jacket with hood. Umbrellas are a struggle and less than functional in high winds that accompany thunderstorms. That said, Brits seem to like their umbrellas. We encountered two Englishmen who topped Ben Nevis carrying umbrellas. (It was a blue sky day so they didn't deploy the umbrellas).

You're so wise to be figuring this out now. A few years ago, we hit quite a cold and rainy spell in Scotland (in July) and I found my trusty travel shoes to be woefully inadequate. Unfortunately, my search for warmer shoes wasted far too much of my time. The clerk in the first shoe store I went to took one look at my feet (size 10) and said, "Oh, dear."

Edgar has really good advice about rain gear. You need to accept that it will rain and that you WILL NOT let it spoil your holiday. The rain doesn't always come in down pours. It's quite different from midwest rain. It's coastal and so doesn't always last. It's all very changeable. I too recommend a good rain jacket with a hood. Umbrellas are a pain.

Pam

Listen to Edgar! The Hebrides and Orkney especially scream (goretex/eVent) hiking boots, or at least hiking shoes. And the Smartwool socks(or equivalent) are just that; Smart! And remember to break your boots in first! Warm, cosy, dry feet with good traction will take a big weight off your mind.

Waterproof hiking boots and waterproof jacket is the way to go.

Bring two pairs of sneakers..if one gets wet you have the other..

My preference is a breathable waterproof rain jacket with hood

I recommend adding a cap or a visor. This will keep the hood better arranged and prevent it from going over your eyes. It also protects the upper part of your face - especially convenient if you are wearing glasses.

Just back from Edinburgh where my well-sprayed New Balance walking shoes kept out the rain, but I would take a worn-in pair of real boots on the trip you have planned, for two reasons- waterproofness and foot protection. Scotland is one huge rock and you need to protect your toes and ankles when going to the outdoors you have in mind. Mud is also deeper than shoe-height if it rains. Just got a new pair of Goretex Lowa boots after my Keens wore out. The best boot is one that fits you and is warm and waterproof, You may want to pick up a small penknife (not in carry-on luggage) to clean the boots out. You can wear your hiking boots to the airport. Do pack some merino wool clothes/underwear/socks - May can be chilly that far north. Edinburgh in November was freezing!

Hah! One huge rock. Very true. :)

I tried a very simple and inexpensive thing. I bought a pair of the Skechers Go Walk shoes from Costco. (under $30). I then put several coats of the NikWax that is intended for leather and suede. (It was what we already had, so that cost nothing extra.) The NikWax didn't change the texture or appearance of the shoes even though they are a stretchy fabric instead of leather or suede.
Not only were those shoes extremely comfortable, they adapted well to all types of terrain in Scotland and kept me sure-footed. Best of all, they stayed dry even when immersed in puddles and constant rain. After all the miles I put on them, the soles are already pretty worn down. So my first regret is that I didn't snap up a couple more pairs when Costco had them. My second regret is that I bothered to pack more durable boot-genre shoes. Those were heavy, took up a lot of space and I only wore them once because they were hot and uncomfortable compared to the lightweight, spongy-soled Go Walks.