Before you start worrying about what to wear, you need to work out what you like, what suits you and begin to develop that all-elusive personal style.
Comfort is the key to confidence in what you wear. So, before you start thinking about what to wear or purchasing something new, you need to work out what you like and what works for you and your lifestyle.
In fact, according to Theo Poulakis, co-founder of men's luxury department store Harrolds, comfort trumps following a dress code blindly.
"Yes, it's important to dress for the situation, but it's more crucial that you understand who you are and can carry off what you wear. There's nothing worse than someone dressing in a style he doesn't feel comfortable in – he stands out," he says.
"A man should develop his own personal style through travel – either physical or over the internet. Then he can address each and every situation and dress in a way that suits his style, his sense of panache and confidence."
When you have your own sense of style, you can basically break any fashion rules, as long as your outfit fits well, compliments your body shape and colouring and is respectful to your host or guests.
However, that doesn't mean you have to be daring, follow trends or splurge on designer clothes, says Patrick Johnson, a designer and owner of tailor P. Johnson in Sydney.
There's nothing wrong with living in a t-shirt and jeans, as long as you're not hiding in them, he say – a man with style should be comfortable mixing an old pair of jeans with a designer jacket.
"I think one of the worst things is people not dressing for themselves, people who copy other people's styles rather than having something a bit more natural that suits them," says Johnson.
Just like decorating an apartment, finding out what suits you is an ongoing process. To help you begin your journey we've broken down the style of several noteworthy fashion icons throughout the past century.
Icons: Mark Ronson, Bob Dylan, Serge Gainsbourg, David Bowie
Style: Mod eclectic - these trendsetters made slim cut suits their own with bright colours, sharp cuts, attitude and interesting accessory choices.
Essential pieces: A bright suit, an attitude of extravagance, a skinny tie, a pair of Ray Ban Wayfarers, high tops.
Shop: Arthur Galan, Saba, Lanvin, Dior Homme, Harrolds 'The French' suit, Ray Bans, Marcs, Jack London, Pierre Hardy, P. Johnson, Alexander McQueen, Zara, Yves Saint Laurent, PS by Paul Smith, Givenchy
Icons: Ryan Gosling (formal), Nick Wooster, Errol Flynn, Tommy Nutter, Michael Caine
Style: Forward tailoring – classic, masculine suits with a twist. These men boldly mix up colours and fabrics and experiment with new cuts.
Essential pieces: A good tailor, a well-cut grey suit, a double-breasted sports jacket, chinos and an assortment of pocket squares.
Shop: Thom Browne, Topman, Brioni, M. J. Bale, P. Johnson, Paul Smith London, Harrolds British suit, Brent Wilson, Oxford, Comme des Garçons Hommes, Zara
Icons: Adrien Brody, Brad Pitt, Bradley Cooper
Style: Elegantly dishevelled – these guys are confident and comfortable in their own skin (rugged good looks don't hurt) and wear clothes that are relaxed yet still stylish.
Essential pieces: A scarf, a great pair of jeans, a white linen suit, an open-collared shirt.
Shop: Hugo Boss, Zegna, Levis, Ralph Lauren, Country Road, Jil Sander, J Brand, Arthur Galan, R. M. Williams, Oxford, Gucci, Zara, Burberry Prorsum, Richard James, Canali
Icons: Johnny Depp, Lenny Kravitz, David Beckham
Style: Daring casual – these men don't shy away from accessories. The look is part rock 'n' roll and part relaxed, but always confident.
Essential pieces: An excess of jewellery and accessories, a leather jacket, biker boots, a good white t-shirt, a blazer and jeans.
Shop: Rick Owens, A.P.C, Balmain, Hugo Boss, Ksubi, John Varvatos, Maison Martin Margiela, markets, vintage shops, Levis, Bassike, Diesel, Brent Wilson, Antoine+Stanley, Zara, Gucci
Icons: George Clooney, Cary Grant, James Bond
Style: Gentlemen with expensive taste – this look is all classic. Perfectly cut tuxedos, bow ties and sharp tailoring.
Essential pieces: A black tuxedo, black suit, patent lace-ups, white shirt, tan chinos and a white polo shirt.
Shop: Giorgio Armani, Dior Homme, Brioni, Tom Ford, Dolce and Gabbana, Polo Ralph Lauren, Eremenegildo Zegna, Kiton, Farage, Herringbone, Yves Saint Laurent
Icons: Steve McQueen, Paul Newman, Tom Brady, Ryan Gosling (casual)
Style: Boy next-door meets mother's worst nightmare – this All American look mixes wholesome values with a bad boy attitude.
Essential pieces: A shawl cardigan, jeans, a leather or letterman jacket, chinos, converse shoes and a white t-shirt.
Shop: Ralph Lauren, M. J. Bale, Levis, The Acadmey Brand, Scotch & Soda, Thom Browne, Persol, Converse, Paul Smith, J. Crew, Richard James, Oxford
Icons: Duke of Windsor, Prince Charles, Tom Ford, Barry Humphries
Style: The Noblemen – it's not surprising that most of these icons are royalty. The look is all about tradition, beautiful tailoring and expensive fabrics. Tom Ford brings the nobel style into the 21st century.
Essential pieces: A selection of perfectly tailored suits for all occasions (including a morning suit), a top hat, hand-stitched Italian silk ties and pocket squares, bespoke shoes.
Shop: Brioni, Tom Ford, P. Johnson, Anderson & Sheppard, Gieves & Hawkes, Barbour, Church's, Artioli
Once you know what you like, you can take inspiration from different styles and use accessories to make a look your own.
And by accessories we don't mean novelty ties and socks – remember that everything you wear, from your pocket square to your stubble, says something about your personality, according to Melbourne stylist and fashion writer Philip Boon. What message do you want to deliver?
"I think attention to detail has been lost – it marks a gentleman," says Boon.
Here are some of the most useful accessories for stamping an outfit, and how to wear them properly:
Watch: As simple as it might be, you need to invest in a beautiful watch that can carry you through day and night. For many men, this will be the one accessory they wear everyday, and as such it sets the tone for everything else you wear. Still checking the time on the scratched Tag Heuer your uncle gave you for your 21st? That's fine, but it doesn't set the bar high for the rest of your outfit. A simple, silver watch that's neither too sporty nor too dressy serves well, says Donny Galella, a stylist with Westfield and fashion writer.
If you wear a ring everyday, don't forget to wear your watch on the other hand in order to balance the look out. You don't want to go over the top with accessories.
Ties: A hand-stitched, silk-lined tie is the way to go, according to Poulakis, as a good quality tie can last you a lifetime. Your tie or bow tie should usually complement the rest of your outfit, not stand out on its own. Classic patterns and colours will always work, whether on a bow tie or necktie. A four-in-hand knot is the most versatile way to wear your tie and looks slightly more relaxed than a half-windsor.
Socks: Coloured socks can add personality to an outfit, but stick to block colours in muted shades such as olive, navy, burgundy, mustard or grey. Avoid patterns as they can be difficult to match. Many men choose to go without socks and wear their trousers a little shorter. This is a great, fresh look, but make sure you either wear bare ankles or socks that cover the whole region – having a gap of skin above a sock isn't a good look, says Poulakis.
Cufflinks, tiepin, jewellery, buttonhole pin, collar pin: These are all great ways to add personality to an outfit, but just remember that less is more. You don't need to wear all of these in order to make an outfit work. In fact, just one or two will suffice, says Galella. You'll get further relying on the cut or your suit and how it sits on your body than by flashing accessories.
Pocket square: The pocket square is one of the easiest ways for a man to dress up an outfit, says Galella. One rule to bear in mind is that the pocket square should always compliment but never match your tie completely, otherwise you'll look like you're at your high school formal. Also, you want to only have an inch or so of your pocket square showing, unless you have a really bold personality. Anything too loud or voluminous is likely to outshine the rest of your outfit (and can look unsophisticated).
Lighter, wallet: You want to look for sleek design and good quality here. It's never flattering to have a bulky wallet in your pocket – not only does it ruin the line of your pants, it also makes you look like a hoarder, says Galella. A leather billfold will suffice for a night out, and a sleek, metal lighter will look far better than a $2 number you picked up at the convenience store.