For those who travel often, finding the right footwear saves time. Go for a pair of shoes you can rely on, and it helps alleviate any pre-flight packing despair. Loafers are often thought of as good travel shoes. And they are, but they don’t work in all scenarios. Instead, opt for a chukka boot.

I have yet to find a place where they don’t work. From a dive bar in New York City to the Saudi Arabian desert, they just look right.

There is a certain ease about chukkas, which might be down to their simplicity. The design is essentially made up of three pieces of leather or suede, stitched onto a simple crepe or rubber sole. Built on last 336, Crockett & Jones’s Molton has a square toe shape, giving the otherwise casual chukka a slightly sharper silhouette. Made from the brand’s signature rough-out suede, it will take on a unique patina with wear, lightening in colour and developing a slightly rougher appearance.

Molton chukka boot, £505

My affinity for Crockett & Jones lies in the heritage, the craft and quintessential styles like the Pembroke. They represent the best of English manufacturing and aesthetics.

While many other things in my life have come and gone, the Pembroke has retained its place as a top performer in my footwear rotation. Like a trusted old friend, these brogues have been my companion in many different phases of my life.

I’m not exaggerating when I say these are the most essential piece of my wardrobe. If I’m heading out on a long international trip: Pembroke. Dinner with my wife: Pembroke. I wore them to Iceland and all over the hills of Augusta golf club during the Masters. They are comfortable for a long day of walking the bustling streets of Tokyo, or a messy day outdoors in Montana – a storm welt construction adds extra waterproof protection to the sole. There’s nothing I trust more for an adventure.

Pembroke brogue, £595

I’ve always loved loafers, but loafers haven’t always loved me. The first pair of shoes – actual shoes, not trainers – that I remember owning were a particularly snappy pair of kiltie tassel loafers. I was 11. As I recall, I paired them expertly with white towelling socks and a particularly vivid pair of check trousers for a school disco. I’ll just leave that with you.

Yet, decades later, none of my own loafers seemed to fit me particularly well. My beloved collection of pennies, tassels and slippers caused me to blister like a sunburnt sausage. I mentioned my predicament to Crockett & Jones’s marketing maverick, James Fox, during Pitti Uomo. A few weeks later, I’m in the Jermyn Street store, surrounded by shoeboxes under the tutelage of a very patient member of staff.

The longer-vamp models, including the Harcourt and Crawford, were like Cinderella’s slipper on me – elegant and secure – while the Antibe, a summer style from the Riviera collection, was also surprisingly comfortable. In the end, I went for a dark brown Crawford, quite a formal fellow, sleek and chic and consequently excellent with tailoring.

Harvard 2 penny loafer, £475

My love affair with boots started young, as witnessed by a small pair of red leather booties my mum kept from when I was tiny. Then, aside from the football variety, there weren’t many boots in my life until my teens, which is when I discovered the joys of what I have come to see as a solid sartorial full-stop to any outfit. A pair of maroon suede Chelsea boots were fun; as were the blue suede pirate boots I had for a while (the less said about them, the better).

Graduating from post-punk suede numbers to the types of boots I wear today is a process that mirrors a more general growing up. Crockett & Jones does the whole spectrum, naturally, but my current obsession is a pair of rough-out-suede Islays, which I wear with everything – pinstripe trousers, flannel trousers, jeans, chinos, suits, whatever. I like the idiosyncrasy of a high boot with eyelets and broguing in tough and weathered brown suede, and with a Vibram cleated sole, paired with a blue wool suit and dark roll neck. It’s a statement. But not a showy one.

Islay boot, £585

Penny loafers emerged as an American trend in the ’50s, but weren’t embraced by pinstriped yuppies this side of the pond until Thatcher set fire to financial regulations in the late ’80s. Today, Crockett & Jones has developed the Boston 2, its first loafer designed specifically for winter, in rough-out suede. In its most recent seasonal collection, the company has taken the robust, waterproof leather, married it to its bestselling Boston penny loafer, added a lightweight but, importantly, grippy rubber sole and come up with this new design – aka, the Winter Loafer.

The Boston, I have on good authority, already enjoys a hardcore following, accounting for a significant volume of Crockett & Jones sales around the world. Add a little dubbin now and again to maintain the suede’s water resistance and keep things looking fresh. Or allow the material to “rough-up” with wear, adding to its ruggedness.

Boston 2 penny loafer, £515

I’m here to admit that my days tottering to meetings in high heels might be behind me. My wardrobe is full of these beauties – many pointed, some strappy, most complicated to get into – which I have collected over 16 years of working for glossy magazines. From Manolo Blahnik to Dior, my collection has become a pride and joy, but how often do I actually wear them? Only if a chat with a cabbie and an evening of sitting down is involved.

Having recently worn loafers to a wedding in Amsterdam, I realised that now is the age of the flat shoe. And my favourite, the loafer, is having a moment.

Crockett & Jones’s Lilou loafer is like floating on a cloud. And, colour-wise, it has you covered. The heavenly dusty pistachio calf suede works beautifully with a white dress or even denim cut-offs. The other calf suede hue is tan – an essential for every wardrobe. These transition beautifully into autumn with country trousers or tailored jeans, making them a reliable year-round choice.

Lilou, £525

Suede shoes. Suede boots. Don’t be shy. Be fearless, be bold, work them into heavy rotation. Suede shoes communicate a well-rounded man. He is at home in the theatre, in a fine art gallery, next to the fireplace in the pub. Suede suggests a type of sartorial fearlessness, an honest acceptance that clothes get marked and scuffed and age over time.

When it comes to footwear, my pick is Crockett & Jones’s Westfield semi-brogue Oxford in tobacco calf leather. Some Englishmen are reluctant to wear brown shoes with blue suits, which is a rare oversight for a country that has given well-dressed men so much. If that frightens you then the easiest gateway for suede shoes is a grey flannel suit. This is a combination meant for each other. When I see a man wearing this divine combination, I know he and I have something to talk about.

Westfield, £575

Black is the colour of the Antwerp Six, German existentialists and Beat poets. It’s also the colour of London and Paris. Black shoes sing in the gloom of Northern European winters, where they seem to blend in with the colours and tones of the urban landscape. For me, it was a pair of Crockett & Jones black Chelsea boots that finally sealed the deal.

Rarely has a pair of shoes made me feel so… well, complete. They unlocked new and stylish combinations in my wardrobe. Including a Tom Ford-era black Gucci suit, which I wear with a black rollneck. One of the wonderful things about dressing head-to-toe in black, besides the louche, sleek sexiness, is that it’s so easy. No need to coordinate colour and pattern. It takes about 10 minutes to get dressed in an outfit that is about as glamorous as it is possible for a man to look, short of black tie.

Chelsea 8 boot, £630