This would be my boot collection if I had free reign to buy anything I wanted. Starting from shortest:
I would have to have a pair or two of the classic Converse all-star hi-tops. They are great to wear in the summer.
I would also get a couple of pairs of other ankle boots, probably skate hi-tops or basketball boots. From the age of 16 until my early 20s, I wore basketball boots pretty much all the time.
As an alternative to skate or basketball boots, I might get a pair of low-cut boxing boots. These should be ok to wear with shorts.
Next in height, the tall Converse and mid-cut boxing boots. When I was in my late teens, I had a couple of pairs of converse-style tall boots which I wore as much as possible. I was quite disappointed when they finally fell apart and I couldn't find any more in the shops.
While I'd love a pair of genuine Converse x-hi, they are quite expensive and not easy to find in my size. These boots from Demonia would be a great alternative - and they have zips up the side so they would only take seconds to put on.
I would have to have a pair of mid-cut Adidas boxing boots. I love my old pair of Tygun boxing boots. Since they aren't available any more, I would probably get a pair of the Tygun II boots.
Getting all sensible and practical next, I would get myself a pair of rigger boots. These would be my gardening boots when the weather is too warm to wear wellies. Since these boots are designed to be worn with the trousers tucked inside, I'd be able to wear them like that all the time.
I would have to have some sort of mid-length leather boot, possibly Doc Martens.
Or possibly a Demonia boot.
Next, high-cut boxing boots. I am actually getting a pair of these Lonsdale boots soon.
When I was at university, I had a pair of these Adidas Box Champ. Back then I didn't have the confidence to tuck my trousers into them and wear them in public, but I often wore them like that when I was on my own.
Getting closer to knee-length, there are the ultra-tall Converse-style boots. These boots usually have zips up the side so they will be easy to wear. Demonia have a wide range.
Alternatively, there are these boots from 'Refuse to be usual', on ebay. They come in a wide range of styles:
I would have to get a pair of knee-length or almost knee-length leather lace-up boots. I already have a pair of 20 eyelet Doc Martens, which are as tall as many wellies.
Or there are many different boots available from Demonia.
I would have to get several pairs of wellies. One pair would stay near the back door so I could wear them in the garden. Another pair might live by the front door if I needed to wear a pair when I left the house. A third pair would be kept in the car in case I needed to wear some while I was out. I would probably also keep a 'clean' pair for wearing indoors if I felt like it.
I wouldn't just get traditional rubber wellies. I would also get a few pairs of leather 'country boots'. They would be great to wear inside or outside trousers. I could walk around wearing them and nobody would know I was wearing knee length boots.
Moving higher than knee length, there are some available from 'rtbu'. I wish these were available in my size - they look perfect to me.
Otherwise there are these 'thigh length' boots, which would be fun to wear, and are available in larger sizes.
I have never worn fishing waders but I'd be tempted to get a pair to try. I think I would have to get an 'all in one' pair like the Le Chameau at the bottom of the page. They look like an actual thigh length boot rather than a normal pair of wellies with 'leg extensions'.