Joseph Cheaney, whilst expensive, will save you £££ in the long run (and theyre a classy shoe)

I like Cheaney and Crocket & Jones. Church's is popular but a little overpriced compared to the others. The classic Chelsea boot has a leather sole but both Cheaney and Crocket & Jones make them with rubber soles which are much more hard wearing. Crocket & Jones make them with Dainite soles which last years and cope with all weathers.

Expect to pay £400-450 for a new pair (more in London) and remember to get some conditioning cream like Saphir Crème which is to be used regularly. You can wax them if you like but not necessary for caring purposes. When the soles finally go you can get them resoled at the factory they were made in for around £100 (less than a pair of trainers). My Dainite soles have lasted over 3 years of daily use.

If you are close to the area you can go to their factory shops and often find shoes with slight imperfections for half the price.