We men have it easy: a black tie dinner means just that, business dress is a lounge suit, and smart-casual is a nice shirt and a pair of chinos. Contrast this with my wife, who, for example, wants to know if ‘black tie’ means an evening or cocktail dress – and while she hates to see anyone else wearing the same dress I can grin wryly and cheerfully complement the other man on his good taste in clothes.
Nonetheless, simple or not, I think there are five staples in a man’s wardrobe that form the backbone of almost every outfit.
A good pair of boots
I prefer boots to shoes as I think they look a bit smarter while simultaneously adding a contemporary twist to your look, but if you’re a die-hard shoe wearer then I won’t argue too strongly that you’re wrong.
I wear Clark’s Desert Boots almost everywhere, but when the ground is wet and muddy I turn to my Timberland Icon Boots. They’re waterproof and the Vibram sole gives outstanding traction in even the deepest mud. They are as tough as, well, old boots, and mine still look as good as the day I bought them five years ago.
If I need to dress up a bit then R.M. Williams’ Comfort Craftsmen boots
fit the bill. They are another design classic and while they are fiercely expensive, everything R.M. Williams makes is beautifully crafted and worth every penny of the asking price. I expect my pair to see me out.
Tip: Try not to wear the same pair of shoes two days running. If you give them time to breathe and dry out they’ll last a lot longer – and smell sweeter.
A decent pair of jeans
I’ve bought jeans from R.M. Williams before and been very happy with them, but I keep returning to the classic Levi 501 for their fit and heritage. The button fly can be a bit of a faff, but given that the zip is the weakest point on any pair of trousers I’m happy to put up with it.
For those times when denim jeans don’t feel smart enough, I fall back on my Ralph Lauren khakis in thin cotton that are relaxed yet smart enough for the sort of business meetings I’m invited to. I would never pay full retail price for them, though; I just pick up two or three pairs at a time when I see them at my local Ralph Lauren outlet store for around £30.
Tip: Washing denim jeans inside out will help stop them fading.
Read our guide to the perfect men's jeans
A tailored shirt
A white, light-blue or discreet checked shirt will carry you seamlessly from a business meeting through to drinks and an evening meal but it will only work if it is made from top-quality cotton and tailored to suit your body-shape. If you’re as lithe and fit now as you were in your twenties then a slim-fit shirt will look fantastic, but the rest of us are probably better going for something with a more flattering cut around the waist.
The two things you need to take into account when assessing the quality of a shirt are the thread count and the ply. The thread count refers to the number of threads per square inch and the higher the number the thinner the cotton thread and the finer the weave. A good shirt will have a thread count of 100 or more.
The second thing to look at is the ply. A single-ply shirt is made with single threads woven together, while a two-ply shirt refers to material that is made by twisting two threads together before they’re woven. It follows that a two-ply shirt with a high thread count will be of higher quality than a single-ply with a lower thread count.
Tip: Try the military tuck to keep the front of your shirt flat and neatly tucked in.
A fine-knit jumper
A blue or grey jumper can be worn anywhere from the boardroom to the bar. I’ve got a lovely alpaca wool example that is wonderfully soft and light but very warm. Alternative materials include cashmere and even cotton, and the little details are what make such a simple piece of clothing stand out: mine has a half-roll neck and is flatteringly slim-fitting, even on me, so try plenty on to make sure you find one that suits you.
Tip: Don’t be tempted to buy a cheap cashmere jumper; with wool you very definitely get what you pay for.
A well-fitting sports jacket
I have two sports jackets: a loose-fitting Camel sports jacket in dark brown and a tailored tweed jacket from Aquascutum.
The Camel jacket is a bit slouchy and loose fitting, but that’s the way it’s meant to be and it looks terrific in a casual, slightly rumpled way.
My tweed jacket is made from bold, checked lightweight tweed. It fits me quite closely, so looks smart enough that if I’ve misjudged a meeting and everyone else is wearing a suit I just look like a mildly eccentric creative rather than a bum who couldn’t be bothered to dress properly.
Tip: eBay is a great source of vintage clothing. I bought my Aquascutum tweed jacket there and it is infinitely better made than the modern stuff. It cost me £20 and I paid about the same again to have it tailored to fit me, which is a fraction of what a new one would cost.
Our guide to finding the leather jacket that suits you