Haha yeah that's always been my problem. What I like isn't trendy, which makes it hard to find. Fortunately my current shoes are only maybe a year old so I've got a good couple years before it becomes a problem.
I recently bought motorbike shoes. They're high-tops (to prevent my ankle being crushed in an accident), look good, and are incredibly comfortable. I'm toying with the idea of just switching to motorbike shoes for day-to-day use when my current shoes need replacing lol
Thanks for the recommendation. I took a look but didn't see anything I liked. To me, they give off a middle aged divorced dad look that I'm not quite old enough or divorced enough to pull off