A reader asks - what shoes should I wear?

I received this recently -

'Just a quick hello to say I am enjoying your blog very much . As a man in my forties I am finding it harder to find clothing that I feel "is me". From reading your post it seems I am doing something right, but shoes, now that is a tough one; having spent my time wearing bike and baseball boots, shoes are proving to be a difficult choice. By the way, I am more often than not in a pair of selvedge Levi 511s and an oldish Belstaff Mojave; any advice as to footwear to complement these items?

Please keep up the good work .
Best Regards
David'

Belstaff Mojave

Grey Fox's reply -

Thank you for the comments, David. You're right that the correct decision should be made about shoes. How often do you see a well-dressed look ruined by bad footwear; too pointy brogues with a nice suit, trainers with anything except sports gear, scuffed and down-at-heel boat shoes with good casual clothes?

As you get older it's best to stick to classic footwear. Anything too radical will smack of trying too hard. Look out for traditional brogues, desert boots, boat shoes, loafers or boots. In hot weather, driving shoes, espadrilles or (in the right context) Converse look good - avoid Crocs and sandals with socks.

To answer your specific question, what to wear with a Belstaff jacket and jeans? This look has its roots in biker wear, so try a pair of boots, monks or more chunky brogues or oxfords. Avoid cowboy boots, unless you live in the US in cowboy country. I'm going to choose these stunningly elegant Cambridge derby boots, made by Alfred Sargent and Sons, from Tails and the Unexpected.