Being a fashion writer and a style consultant, the biggest gripe I hear from men has always been some version of: Sure, I understand what to wear to work, but how about dressing elegantly outside it?

That dreaded term: smart-casual. It’s enough to rouse wardrobe-related anxiety for almost anyone. Is a suit too smart? Are jeans too informal? Can I still wear trainers? Whilst we’re not going to ...

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