I would have a look, and do some more research, try and find boots and styles that your like and want to make your own. Look online to see the boots in the wild, worn with what outfits. I would say that a good pair of boots would be a sound investment, and with quality leather they will look better with age.
Again if you can afford it, go for some boots that are goodyear welted so that you can get them resoled in the future.
Also on the smart-casual spectrum I would go for a classic style, toe cap or elegant brouging. Going for a grain leather makes it more casual, and lighter shades such as tan.
Moreover, if you want something that is in-between stylish and has the heritage have a look at End's collaboration with Trickers.
END. x Tricker’s Spring ’14 Collection « End Clothing Blog
Die, Workwear! - Shoe Options for Rainy Days