It’s hard to take someone seriously in a lousy or slightly adventurous pair of shoes (apart from Steve Jobs, no-one really seemed to care about his Merrells for some reason).
The shoes you wear and the condition they're in say a lot about you. Especially the shoes you wear to work. Not necessarily the mark of a man but a good starting point if you're of a judgemental persuasion.
I'd therefore always err on the side of caution and keep to classic styles when picking shoes to wear with a suit for the office.
Here are five pairs very much at home in the city. None of them are cheap, granted, but they'll last you a good few years and in some cases a lifetime with a bit of care and the help of a good cobbler.
1. Russell and Bromley- Keeble 3 Tassel College Loafer £175 (pictured above)
2. Church’s- Chetwynd Brogue Polished Leather £390
3. Bass Weejuns- Larson Loafer Shoe £95
4. Loake Dorchester Oxford Shoe £199
5. John Lobb Monk Strap Shoe £675