Looking stylish does not have to be so complicated. You might read guides on how many suits you need, what shirts, what jackets, this brand, that brand, etc. While fashion comes and goes, trends change so quickly it's hard to keep up! But style is eternal. So here are the 10 items you need to look good now, in 5 years from now, and 20 years from now.
Item #1 - The Bespoke Suit
You might not wear suits all that often and might think, "is a bespoke suit worth the investment?". The answer is a resounding yes. Having a bespoke suit is an experience in itself, but the result is a garment made for your body that can be re-altered as your body changes over the years. And since it is not made in an overseas factory but handmade by tailors, the quality will be second to none and will look good for years to come.
Item #2 - White Oxford Button-down Shirt
The most versatile shirt you can own and also the most timeless. You can wear it with jeans and a leather coat, or with that bespoke suit of yours. And it only looks better over time as the more you wash it, the softer the cloth becomes. It looked good back in the day on Paul Newman (photo below); it looks good today and will look good in 10 years.
Item #3 - Raw Denim Jeans
Why specifically raw denim jeans? Aren't they extraordinarily stiff and rigid at first? That's the point. They age with you, fading gracefully in all the right places according to your movements. Whether you rock them with a t-shirt, polo shirt, or even with your white button-down shirt and a sport coat, you'll always be in style with a sturdy pair of these.
Item #4 - White T-Shirt
From James Dean in "Rebel Without A Cause" to the stylish gents on Instagram who wear them under sportscoats, the iconic white t-shirt can be worn with everything from jeans and bomber jackets to a fine-cut suit to shorts. Simply put, it's never gone out of style and never will.
Item #5 - Leather Oxford Shoes
If you only needed to own one pair of dress shoes, these are it. Either in black or brown (matter of preference), you won't hear much about them being a hot trendy item. Instead, they are a dependable staple. If you buy the best you can afford, you can keep them for a long, long time by having them resoled every few years and they will always look good. Wear them with your suits, dress pants, and sportscoat, or even with blue jeans (make sure you're wearing at least a button-down shirt up top).
Item #6 - Silk Necktie
Specifically, a silk necktie 3" in width in either a plain navy blue or a repp stripe design. Why 3"? Because trends in neckties have varied over time from extra wide to skinny. 3" is an excellent sweet spot that will always look good. Any why navy or repp striped? Because navy can match any color suit or shirt color (especially that white oxford shirt mentioned above!). And a repp stripe can likewise match any suit or shirt. Please look at how I've worn the same navy tie with a gingham check shirt and a mannequin with a repp tie and white shirt.
Item #7 - Leather Jacket
From Brando to McQueen to Travolta. The leather jacket has been immortalized as a style staple through film and with good reason. You can get a variety that suits your style, a biker jacket, bomber jacket, or trench coat. A leather jacket is just a timeless item that ages like a fine wine. All the creases, wrinkles, and fading over the years tell the story of your style over time. It can look fantastic with jeans and tees, chino and sweater, or if you're bold, with tailored clothing.
Item #8 - Wool or Cashmere Overcoat
Nothing looks better with a suit or sportscoat in the winter than a gorgeous camel, navy, or grey overcoat. Look at photos of well-dressed men throughout the years, and they all sported overcoats in cold weather. You can choose many details: single or double-breasted, patch pockets, belted or not, etc. And depending on the quality, you can own the same one for decades. I wear a navy Brooks Brothers coat I purchased on eBay, and it dates from at least the 1960s. And don't be fooled into thinking it only needs to be worn with tailored clothing. Dress it down with jeans and a sweater or hoodie, and you'll look great.
Item #9 - Roll-Neck Sweater
Also known as the turtleneck sweater, it is a versatile friend in the wardrobe. Whether in cotton, merino wool, lambswool, or cashmere, you can wear them in almost any way. With a pair of flannel trousers? Sure. Under a suit? Absolutely! Just with a pair of jeans? Yup!. And it is a garment that has stood the test of time. From Clark Gable to Kirk Douglas to the stylish men of Italy today, it looked great then, and it does now and will continue to.
Item# 10 - Watch
Admittedly, I am not a big watch fanatic. However, I do own 1 good watch and believe that it is one of the keys to timeless style. Brands with history such as Omega, Rolex, Patek Philippe, or more affordable yet stylish brands like Movado or Daniel Wellington. It is an accessory that has adorned men's wrists throughout the 20th and into the 21st century and shows no signs of disappearing anytime soon.