Expensive, ultra-expensive, and exceptionally pricey are the categories of items I'm about to delve into in this article. These pieces represent the gold standard in men's fashion, standing the test of time and remaining stylish year after year.
Before you wince at these sky-high prices, remember that there are plenty of similar options out there that won’t break the bank. It’s not too hard to find alternatives that are equally stylish and classic 🙂 (though, if you're eyeing that Rolex at the end of the list, perhaps it's best to save for the real deal rather than settle for a fake).
Baracuta Harrington Jacket
Few jackets have endured the passage of time quite like the Baracuta Harrington, also known as the G9. Since its debut in 1937, this jacket has been a favorite among golfers due to its water-resistant fabric and distinctive umbrella-shaped back flap. It quickly captured the hearts of style icons and everyday wearers alike.
The legend Steve McQueen in a Baracuta G9.
Each Baracuta Harrington remains handcrafted in the UK, showcasing a design that has remained remarkably consistent since its inception. With a tartan lining that strikes the perfect balance between smart and casual, this jacket is versatile enough to pair with everything from button-ups and ties to simple tees.
Burberry Trench Coat
The trench coat is the pièce de résistance of Thomas Burberry, and it continues to dominate the brand's collections to this day.
What sets Burberry's trench coats apart is their signature water-resistant cotton fabric (typically gabardine or poplin), which is lightweight yet incredibly durable - thanks to its invention by Burberry in 1879.
With a double-breasted design featuring 10 buttons, a large collar, and a waist belt for a tailored fit, these trench coats flatter tall figures and exude style. Whether worn over a shirt, tee, or suit, they are a chic alternative to standard raincoats during light showers.
Schott Perfecto Biker Jacket
The leather biker jacket burst onto the Hollywood scene in 1953 with Marlon Brando in The Wild One. Since then, it has epitomized the rebellious yet charming bad boy aesthetic.
Launched in 1937, the Perfecto boasts a storied history alongside its premium quality. Named after Irving Schott's favorite cigar, the Perfecto features thick leather, large lapels, and sturdy zippers, originally designed to protect motorcyclists. Its iconic status was further cemented through collaborations with renowned motorcycle brands like Harley Davidson.
Today, the Perfecto has diversified in style, detail, and color while maintaining its hallmark leather construction - an enduring symbol of Schott's craftsmanship.
G.H. Bass Weejuns Penny Loafers
The classic penny loafer that many modern gentlemen wear with suits originated in Norway. The original loafers traveled across Europe in the early 20th century before finding fame in America.
In 1936, American shoemaker G.H. Bass introduced Weejuns, a refined version of the original design featuring a strap across the instep. Thus, the term "penny" was born.
Still meticulously handcrafted today, penny loafers remain a go-to choice due to their versatility, effortlessly pairing with cuffed jeans, chinos, or a sharp suit.
Converse Chuck Taylor Sneakers
Do I even need to explain the legendary status of Converse? Their most famous sneaker line boasts nearly a century of history, and the classic rubber sole and canvas material of Chuck Taylors continue to be the top choice for millions around the globe.
One secret sneaker aficionados should know: you don’t have to keep them pristine. A little dirt adds character to your Chuck Taylors.
Ray-Ban Aviators
Initially designed for pilots in the 1930s, the first Ray-Ban Aviators featured large lenses essential for shielding eyes from intense sunlight.
It's hard to pinpoint the exact reason for the massive popularity of these shades, but seeing icons like Tom Cruise in Top Gun or Don Draper in Mad Men rocking Ray-Ban Aviators speaks volumes.
Their simple design complements most face shapes, making them a fantastic accessory for both casual and formal occasions.
Levi’s 501
Since their debut in 1873, Levi’s has consistently evolved the 501 line to meet contemporary styles and needs. As a true icon spanning generations, the 501's enduring popularity speaks for itself.
Regular updates keep the 501 in sync with modern trends, ensuring its status as a wardrobe staple.
Are Levi’s 501 jeans beautiful? Absolutely, though the influx of counterfeits has perhaps caused some to overlook their legendary status.
Fred Perry Polo Shirt
The iconic striped polo shirt from Fred Perry transcends mere fashion; it’s a staple in countless wardrobes.
Featuring a modern slim-fit design, Fred Perry’s polos are both stylish and comfortable, suitable for a variety of body types. Those who own one can attest to its superior quality compared to standard polo shirts.
Louis Vuitton Keepall Bag
What makes this luxury bag special is its perfect balance - not too small, yet not overly bulky. Regardless of the size you select, it always provides ample space for essentials on short trips or business ventures.
Since its introduction in 1930, the Louis Vuitton Keepall has inspired countless designs worldwide. If your budget permits, this timeless bag is an investment that could last a lifetime with proper care.
Rolex Submariner Watch
In 1953, the Submariner made waves as the first watch able to withstand depths of up to 100 meters. Rolex touts it as the ultimate accessory for men, claiming, “a diving watch that pairs perfectly with a sophisticated tuxedo.” Sean Connery as Agent 007 proved this, looking impeccable whether submerged in water or attending a glamorous event.
By Fashionbeans
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