How to accessorise like a boss

The finer details are what catch the eye in any executive ensemble and separate the contenders from the pretenders, whether it’s the stately timepiece on the wrist, a pair of exotic leather cufflinks, or a colour-coordinated pocket square.

Whichever accessories you decide to wear, remember that less is more. A good rule of thumb is choosing up to three accessories and ensuring that they’re noticeable but also subtle enough that they don’t dominate your entire outfit.

Go in strong

One of the first rules of accessorising like a boss is having a good foundation—and I don’t mean the type that goes on your face. Accessories will demonstrate your good taste and accentuate your outfit, but if your clothing fits poorly or is of inferior quality, then no-one will even notice the extra yards you’ve gone to with your accessory selection.

First and foremost, invest in a good-quality 100-per-cent wool suit. Wool is renowned for its fineness and breathability, which is ideal for the Australian climate. Wool also drapes nicely against the body due to its elasticity. Second, make sure that the suit actually fits you. Your money is better invested in a custom-tailored suit over a name brand, as the latter won’t matter if it hangs off your frame or it’s too tight.

Choose quality over quantity

It’s far better to invest in a handful of high-quality pieces than a larger selection of mediocre ones. This applies to everything from your socks and wallet through to your tie and watch. Not only will your items last longer if you spend a little extra on them, but you’ll also make a statement whenever you wear them. Don’t underestimate the power of higher-priced items—they can make you feel like a million bucks and translate into that extra bit of confidence you need to land a new client or deal with a difficult colleague.

Watch out

Invest in a watch that’s good enough to pass down as a family heirloom. A watch is more than just a way to tell time, which, after all, you can now do on your phone anyway. Think of it as a status symbol that tells the world you’ve reached a certain level of success. Even if you haven’t reached Rolex levels of financial security, you can lead people to assume you have by wearing the right timepiece.

Choosing the right watch can be a complex, time-consuming, and highly personal endeavour. However, there are a few general rules of thumb you can follow. For corporate occasions, conservative dress watches are best—leave the gaudy sports watches for your nights out on the town. The watch face should be simple and understated, belying the complex Swiss-made mechanics lurking below the surface. Quartz movement watches offer the best balance between precision and ease of use, although Swiss watch purists will insist on the mechanical movement of an automatic or manual timepiece.

Tie yourself down

Chosen well, a tie pulls the rest of your outfit together, but it’s easy to go wrong. Stay away from anything made with polyester; silk ties are the way to go as they feel and hang better, but also last longer than the cheaper equivalent.

You should put some serious thought into the colour and pattern of the ties you wear as this says a lot about your personality. It’s no coincidence that politicians favour red ties as this colour is indicative of power and strength. Patterned ties (think herringbone and houndstooth, rather than some of the more garish designs) suggests the wearer is complex and multilayered, while a purple tie demonstrates self-confidence. For conservative workplaces and occasions, it’s hard to go wrong with a navy silk knitted tie.

Put your money on show

A good-quality leather wallet says much about your station in life, so the higher-quality hide that’s used, the better. A bit of wear adds character to the leather, but if it’s scuffing at the corners and losing its shape, it’s wise to invest in a new one.
Money clips are a versatile wallet alternative that says the holder has mastered the art of gentlemanly accoutrement. There’s something quite powerful about a man who carries a stack of crisp, neatly folded bills in a money clip.

Choose your socks wisely

You may not give a second thought to your sock selection as they’re barely visible when worn with a suit. However, they tell a great deal about you. A man reveals his socks while sitting down, and when he shows colours that are perfectly matched to his shoes or other accessories (such as ties or pocket squares), this speaks volumes about his level of sophistication. It should go without saying that both socks should match in type and colour.

Think outside the (pocket) square

Try to choose accessories that are unique as a way to stand out. You could look for ones that are made out of natural material that’s different to what is conventionally used. A good example is cufflinks. While the vast majority of them are made out of sterling silver, you can make a statement with cufflinks constructed from wood or leather.

Antiques can also be repurposed as vintage fashion pieces, giving you a sense of style that no-one else can imitate. This could be an old pocket watch or tie clip, or even a hand-me-down suitcase. Not everything in your grandfather’s war chest can be resurrected for modern fashion, however. Garish paisley ties and retro bowler hats are best left in the past.

Bring down the bling

Tempted as you may be to wear your wealth in the form of thick gold chains and bracelets, the rule of less being more once again applies. Simple wedding rings are always acceptable, but you don’t want to adorn your hands with too much gold or silver. It’s crass, and gives the sense that you’re trying way too hard to impress other people.