Speaking of trying too hard I thought this was an interesting video. Not because of the shoes, they're interesting on their own, but look at the two men, how they're dressed and how they're conducting themselves.
On the one hand you've got the host. He's trying to teach men the proper rules of dress, and picking out the 'best' things money can buy. He's obviously making money from YouTube and I think he's got a business selling coathangers or something. Look at him though, stiff, uncomfortable, out of place, really looks like he's trying too hard. I don't think he looks good at all.
Now check out the other bloke, the fancy cobbler. He's dressed smart, jacket but no tie, but see how relaxed he is. He's in his element, doing what's natural to him and he just looks so much better and more stylish than the host. It's all the difference between trying too hard and relaxing into yourself, being comfortable in your environment.
Admittedly not many of us have 'luxury Mayfair shoe shop' as our environment but you get my point.
View: https://youtu.be/Z89RdEuCqSA