A Gentleman's Guide to Whisky

Every gentleman should know his whisky. Whether you choose to drink it is another story. You don't need a whisky collection that rivals a Scottish distillery. You simply need to know your way around the menu.

Like a well-tailored blazer or a quality pair of leather loafers, whisky has long been associated with timeless style. Understanding the basics isn't about becoming a connoisseur.

It's about being versed enough to appreciate the craftsmanship, recognise different styles and feel confident whether you're hosting friends, entertaining clients or ordering a drink after work.

The beauty of whisky is that no two expressions are quite the same. Some are bold and smoky, others smooth and approachable.
Much like great footwear, every whisky has its own personality.

The Foundations Every Gentleman Should Know

Knowing some basics surrounding this age-old classic will put you in good stead for multiple settings. Let’s begin with what, actually, is whisky?

At its core, whisky is surprisingly simple. Grain, water, yeast and time. Different grains, climates, and traditions produce remarkably different spirits, which is why a smoky Scotch bears little resemblance to a sweet Kentucky bourbon.

Much like handcrafted leather shoes, great whisky rewards patience. Time, quality ingredients and meticulous craftsmanship all play their part. The production of whisky takes several years, hence why it is so valued worldwide for the patience and skill that goes into it.

Whisky vs Whiskey

Now you may be thinking, why do some bottles say 'whisky' while others say 'whiskey'? Good question.

The answer is geography.

Scotland, Canada and Japan drop the "e". Ireland and the United States keep it, because it’s in their names. Same spirit, different traditions.

Scotch vs Irish vs Bourbon

Which brings us to our next point. Is there really such a big difference between the three, and does it matter? The answer is, yes. What makes these spirits distinct is their geography, distillation methods, and ingredients.

While you would’ve seen bourbon referenced in many movies, we aren’t as familiar with it here in South Africa, and that’s because bourbon is unmistakably American. Corn-heavy, sweet and aged in new oak, it’s easily identifiable from the other two.

Smoky. Rich. Deeply layered. Scotch earns its reputation through patience, spending a minimum of three years maturing in oak before it ever reaches the glass.

Irish whisky is smooth and light and is crafted from malted and unmalted barley, often combined with other grains.

So, the type of whisky people prefer is often tied back to region and craft method, which in turn affects the taste experience.

Despite the common perception, age alone isn’t everything when it comes to whisky. What’s often more important is how a whisky matures, which is dependent on how the spirit interacts with the wood of the barrel and the environment around it.

All of these factors lead whisky to its characteristic flavour notes of vanilla, spice, oak, smoke or caramel.

The Gentleman’s Cocktail Wardrobe

Knowing your whisky is one thing. Knowing what it says about your style is something else entirely.

Every classic cocktail has its own personality. Just like every pair of G.H. Bass shoes.

And not all cocktails are created equally. That’s why we’ve selected the most classic whisky-based drinks rich in history and character, just like our footwear.

The Old Fashioned

For the Traditionalist

Few cocktails have achieved the iconic status of the Old Fashioned. Built on little more than whisky, bitters, sugar and citrus, it's proof that simplicity done well never goes out of fashion.

A staple of Old Hollywood, you will have seen this drink in The Great Gatsby and Mad Men, amongst others.

Think smoky jazz bars, leather armchairs and quiet confidence. For the Old Money look, pair an Old Fashioned with the Weejuns Ornament with slacks, a collared shirt and fitted jacket. Like the Old Fashioned itself, the Weejuns Ornament never chases trends. Its clean silhouette and polished leather have been turning heads for generations, making it the natural companion to a cocktail that has stood the test of time.

Whisky Highball

For the Effortless Charmer

A simple, refreshing blend of soda water or ginger ale with whisky and ice served in a tall glass, this drink appears simple, sophisticated and unassuming.

The Highball is a lesson in restraint. With so few ingredients, quality has nowhere to hide.

It’s a perfect match for the kind of man who prefers understated luxury and quality over status. He orders a highball because it’s refreshing and balanced, not because it’s fashionable.

He isn’t trying to impress anyone. That's precisely why he does.

For the relaxed yet put-together aesthetic, wear a crisp linen shirt with rolled-up sleeves and chinos with the Jetty II Boater 2 Eye to complete the look.

The Manhattan

For the refined socialite

Sophisticated without trying too hard, the Manhattan has been a favourite among New York's well-dressed since the late nineteenth century. Served in a martini glass, strained over ice with whisky, sweet vermouth and bitters, and garnished with a maraschino cherry, this cocktail is made for the discerning type.

The Manhattan deserves an outfit that complements its standards, so think collared shirts with a thin tie and a tailored jacket. The shoe that ties this look together is the Weejuns Larson Moc Penny. Its elegant silhouette and leather shine exude that feel of classic style.

The Boulevardier

For the Cosmopolitan Gentleman

Think of the Boulevardier as the Old Fashioned's more worldly cousin. Rich, bittersweet and quietly confident, it's the cocktail for evenings that stretch well beyond dinner.

A variation of a classic negroni, crafted with whisky, sweet vermouth and Campari, this drink is enjoyed for its balance of sweet, rich and bitter flavours.

Loosely translated, a boulevardier is a man-about-town, crafted for those who are polished, cultured, and enjoy the energy of the city after dark. In terms of aesthetic, think double-breasted blazer over a fine-knit polo with a vintage mechanical watch and tassel loafers such as the Weejuns Larkin Moc Tassel.

The Hallmarks of a Gentleman

Style has always been about more than what you wear. It's reflected in the way you carry yourself, the conversations you have, the traditions you appreciate and the details you choose to notice.

Learning about whisky isn't about becoming an expert. It's about understanding the stories behind the glass, recognising the craftsmanship in every pour and developing an appreciation for things made with patience and purpose.

Much like a great pair of leather shoes, the best whiskies are shaped by time, refined through tradition and admired for their character.

Whether you're ordering a Manhattan after work, sharing an Old Fashioned with friends or stepping into a room wearing your favourite pair of G.H. Bass loafers, confidence comes naturally when it's built on genuine appreciation rather than passing fashion.

Because true style isn't about having more, it's about choosing better.

Shop your next pair of timeless classics online, or find your nearest stockist to buy in store.