There’s more to a good suit than a good fit. That sounds like sartorial sacrilege but it’s true (dig out your prom photos for shuddersome evidence). Yes, a tailored two-piece is the foundation every buttoned-up gent should aspire to, but that’s just the starting point of looking good in formalwear.
Where suiting goes from an art to a science is in the details. You need to know your elements, and they need to know each other. Your shirt must complement your suit. Your tie must complement your shirt. Your pocket square must complement everything. And we haven’t even got to footwear yet.
No matter how much tailoring has relaxed in recent years, there are rules that govern all the above.
First, The Basics
Before we get into the formulae of formalwear, let’s make sure the fundamentals are covered. Since most men rarely invest in a new suit, refresh your current look with a well-stocked rotation of everything else, says Ryan Haynes, a buyer at designer menswear store Coggles. “Buy a minimum of five shirts that’ll complement your suit. Classic white and pale blue go with most things, and it’s worth spending a little extra for the quality.”
Once you start adding accessories, there are two common mistakes men make, says Sarah Gilfillan, founder of personal styling service Sartoria Lab. “There’s either a reluctance to mix patterns, which creates a boring look with a plain suit, shirt and tie. Or, there are too many patterns that shout for attention, and the resulting look is confused.
“The easiest way to match your tailoring is to limit the statement to one piece, and keep the rest plain: a patterned suit with plain pieces elsewhere, or vice versa.”
That covers the basics. The next step requires a masters in menswear, including an understanding of complementary shades, finishing touches and shoe suitability – knowledge that we managed to glean from the experts below.
Suit + Shirt
This is the bedrock of your entire look: get the pairing right and you’re on course to build a suit of armour. Get it wrong and you’ll look like an Apprentice reject.
“A crisp, classic white shirt will never fail, and sits with all suit colours and tones,” says Alan Cook, menswear design lead at Marks & Spencer. “That said, lilac and purple are just two tones that work well with grey or navy suits, while soft greys and periwinkle are sound choices with black or charcoal tailoring.”
If you want to cast your dye a little wider with on-trend coloured tailoring, play it safe by keeping things neutral. If you’re experimenting with a deep green suit or burgundy suit, try a lighter version of the same shade on your suit. The tonal trick also works on more standard colours to give your outfit depth, says Cook. “A cornflower blue shirt with a microprint looks incredible within a wider indigo suit.”
Shirt + Tie
Air ties, roll necks and T-shirts are all fair game under a blazer these days, and with the menswear menagerie so crowded, it’s tempting to put the humble tie on the endangered species list. That would be a mistake. A shirt and tie may sit on the conservative end of the dress code spectrum, but it’s a classic combo for a reason. Do it right, and it’s about much more than looking good. This timeless pairing can make you appear trustworthy and employable.
“The search for a tie can be overwhelming,” admits Allyson Lewis, CEO of The Tie Bar. “There are so many colours, fabrications, patterns and textures, but it needn’t be this way. Once you’ve confirmed the general dress code, identify the overarching colour: your tie should, ultimately, complement the dominate shade with an overall colour or stripe, or opt for a pattern or colour that’s in contrast.”
Try matching a rich blue tie with a sky-blue shirt and dark navy suit for a tonal look, or a red tie for some colour-pop contrast. If you’re wearing grey, stick with muted tones such as brown or burgundy, or choose a black tie for a sharp salt-and-pepper effect. If you’re wearing a black suit, and you’re light skinned, use the tie to dial down the contrast between you and the suit by opting for a warm colour like burgundy.
Lewis also cautions that not all shirt and tie combinations work, and you should swerve ‘holiday cheer’ at all costs. “Avoid any pairings that invoke thoughts of a specific holiday: red and green, black and orange, red, white and blue and so on and so forth. While it is possible to pull off such combos, it’s a delicate balancing act that can come across costumey as opposed to polished.”
Pocket Square + Suit + Tie
From Pitti peacocks to corporate careerists, a pocket square has become an essential component of a suit. A finer detail for sure, but one that’s still subject to the rules.
“A strong match between a pocket square, shirt and tie is mainly based on the colour,” says Danny O’Neill, sales manager at Moss Bros. “It doesn’t necessarily have to be the same print or texture as long as the shades work together.” In fact, something too samey can look a bit too perfect – a bit wedding starter pack. And of course, some colour combinations work far better than others.
Feel free to experiment with material and print, too. “There isn’t an ideal fabric or one to be avoided – with pocket squares you can be as adventurous with the fabrics and prints as you like,” says O’Neill. “However, it is important that the colour should complement either the shirt or tie.”
The safest option is to pair a white shirt with a white pocket square. For a more advanced approach, look for a patterned pocket square where the secondary colour matches the tie, or go tonal with a subtle change of shade between the shirt, tie and square.
Socks + Suit
Justin Trudeau may bask in soaring approval rates, but, sock horror, he doesn’t always put his best foot forward when matching his hosiery with his tailoring. Canada’s leading man has punctured many a strong look with an ill-advised, novelty sock, and every guy should eschew the Chewbacca feet for something more appropriate.
A foolproof technique is to match the colour of your socks with the colour of your trousers. Black on black, navy on navy, fifty shades of grey.
For a slightly less safe (read: boring) approach, look out for subtle details within an outfit to highlight with your socks, says Ryan Palmer, co-founder of The London Sock Company. “Things like the lining of a suit jacket, a colour detail on the belt, or your pocket square or cufflinks.”
Know that some combinations are easier to pull off than others, too. “Classic dressers should opt for black, burgundy or dark greys socks – especially when you’re wearing a darker suit,” says Palmer. “Or, if you do decide to spin the colour wheel, mustard, turquoise and red sit especially well with navy tailoring thanks to the contrast.” If you do take this route though, ensure the vibrancy is limited to your ankles only.
Suit + Shoes
Now, nobody is saying you need a sneakerhead-style walk-in wardrobe, but every man should own at least a few colours and styles of work shoes. A single pair won’t sit with every suit hanging on your rail, but when it comes to matching your shoes and trousers, some are more versatile than others.
Always wear black shoes with a black suit and recycle them for deep navy business suits when you have a day in boardroom. Chocolate brown shoes will work with your staple navy and grey tailoring, and it’s also worth keep something a little less formal in your rotation for dress-down days.
“Deep, dark claret shoes work well across a range of suit colours, from black and navy to dark brown and grey,” says Phill Tarling, a stylist who counts Tom Hardy on his client list. “Tan brogues can be worn with blue and grey suits also, but they don’t work with darker tones.”
It’s not just the colour to consider, but the style of shoe too. “My advice is to keep your footwear simple – a classic brogue, Derby or loafer for a classic suit. It’s much easier to make a statement up-top with your accessories than it is your footwear.”
Cufflinks + Suit
Once you’ve got the main show sorted, it’s onto the support acts. Some well-deployed accessories, like cufflinks, can lift a look from standard to headliner – providing you pick the right ones.
“Wearing cufflinks can be a way to add personality to a formal outfit,” says Kate Regan, head designer at British tailoring outfit Hawes & Curtis. “While some abstract cufflinks are acceptable, they should be out of bounds with a dinner suit or on smarter occasions.” And if you’re wearing a shirt that requires cufflinks, chances are it’s such an event.
“When wearing a white shirt, you can experiment with any colour, pattern or shape cufflinks, unless you’re in a strict formal environment,” says Regan. “Gold designs really stand out against a light blue or navy shirt, while black onyx is better suited to black tie.” So that means having at least two sets in your arsenal, lest you go too Diddy at the office, or too muted at the top table.
If your 9-5 demands a suit, it’s worth investing in fine leather goods to match because you’ll get the wear out of them: the belt, the briefcase and the shoes. But such pieces should chime just as well as the threads on your back.
“The classic rule is well-known: leathers should always match leathers, so if your shoes are brown, your belt should be too,” says Mariya Dykalo, creative director at Aspinal of London. “The rule applies to briefcases too if you’re wearing all-black. However, other coloured suits don’t have to match.” Good news, especially since a good leather laptop case doesn’t come cheap.
“The colour of the leathers you choose can speak volumes about your personality. Opt for all-black accessories when you need to look sharp and corporate, but switch for tan on the weekend. Either way, they should be of complementary colours or varying neutrals. And you can never go wrong with navy – less formal but always classic.”