The top five pairs of shoes you should own

Thursday, January 17, 2013
In the style of previous posts, I thought I might share some views on a useful 'starting cupboard' of shoes. Of course, as ever, this is really just opinion and none of these are strictly required unless they happen to suit your particular style, lifestyle, and habit of dressing. I'm also not sure that I would say to anyone that five pairs of shoes is a 'starting' cupboard, so I've put these in roughly the order I would buy them if I were starting out now, and in this way they could easily be bought over a couple of years as funds allow.

Plain black oxfords
Sure, brogues are prettier, loafers are more comfortable, and brown more suitable for casual-wear, but a man with a pair of plain black oxfords can fulfil with confidence about 75% of all dress codes. Clearly, they're perfect with business suits of all shades, colours and cuts, and would only be inappropriate with very casual weekend suits. They can also, importantly, be worn with black tie (where brogues would not be suitable), white tie (patent leather is correct, but few would criticise black oxfords with a decent polish), morning dress, or just a reasonably smart blazer and flannels.

Brown Brogues
You'll need a casual pair of shoes to fill in the less frequent but more varied occasions where black shoes won't do. Weekend wear, wearing with chinos, wearing with tweed, wearing with jeans (if you must wear jeans), wearing with white cotton ducks to Henley, and so on. Of course, there are other casual shoes that could fill these gaps but few are quite so widely suitable. A pair of brown loafers are ideal with chinos, and nice with jeans, but hardly suitable to wear with a tweed suit. Polished oxblood monks might look cracking with a casual suit but are probably a bit much to wear with chinos and a blazer.


Of course, plain brown oxfords could do a similar job, but a) I love brogues (so you should too) and b) if you're going to have only one casual pair of shoes, it might as well be properly casual.

Deck Shoes
Ok, they might not be for everyone, but they do pick up the last straggling dress codes that wouldn't be covered by the two options above. Shorts, beachwear, that sort of thing. Only the most obsessive of iGent would insist on retaining suit and brogues on the beach or as he takes breakfast on his veranda on a sunny morning in August. For those of us with a pragmatic approach to dress, some kind of alternative is required. For me, at least, that alternative is deck shoes.

Loafers (black or brown)
Personally, I'd choose brown, but go for whichever you think you'll get more use from. If you wear suits Monday to Friday, then black loafers are probably more useful to break up the monotony and to give your Oxfords a rest. (Actually, if you really wear suits Monday to Friday then your second pair of shoes should probably be a second pair of black oxfords. Boring but true. Go for brogues if you want to liven them up.) If, on the other hand, your day-to-day wear is more of the chinos and jacket variety then brown loafers are more useful.


I favour a slim shape with rounded toes and the lowest-profile stitching around the toe possible and, for your first buy, a non-tasseled pair might be safest although I would be the last person to dissuade you from tassels if you're keen. For brown shoes, suede is an option, otherwise polished calf-leather is ideal.

Something fun, or practical
If you have all of the above then you're reasonably well covered, and it's time to pad out your collection. It might be that, for practical reasons, you just need another pair of plain black or brown shoes. If so, now's the time. If, on the other hand, you think you've more or less got what you need, then it might be time to stretch to something a bit different. Really love loafers? Perhaps time to get the tasseled pair. Always hankered after some monks? Buy some in black or brown, depending on your usual mode of dress. Live in a cold country and spend a lot of time wearing tweed? Perhaps go for a pair of brogued boots. Regardless, this fifth pair should give you something else to wear with many of your outfits but also something a bit special that suits your own style and that you'll take a particular pleasure in. For me, it's probably my tasseled loafers. And my brogued boots. And my patent leather evening shoes. I'm incorrigible.