Personally, I'm a fan of Doc Martens, they are my favourite shoes, they look great, they are ridiculously comfortable once broken in (this is quite painful though) and they are waterproof! There is nothing worse than having having your feet soaked at the beginning of a long day. Tan leather has been quite trendy this season so I have my eye on these:
They have a comfy faux-fur lining too for extra warmth :)
Other possible candidates are the Docs with heels. I own a pair of black shiny ones and they are the most comfortable heels I have ever worn. The heel is thick thus stable and the platform at the front reduces the impact of the sole of your foot. I've been looking at these brown ones too:
These look amazing, I love buckles!
Hopefully I'll have some cute sketches for you soon :)
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