Whether you like it or not, chances are you’re going to have to shoehorn yourself into a tuxedo at least a couple of times over the course of your existence. But don’t worry, contrary to what many men would have you believe, getting dressed up to the nines doesn’t have to be a painful battle between man and mirror. Well, not if you know what you’re doing.

First off, you’re never going to fully channel your inner covert MI6 agent if you don’t have a Bond-like confidence in your outfit. So, if you know that underneath your immaculate dinner jacket, you’re concealing a shirt so ill-fitting it could give Jeremy Clarkson’s favourite pair of jeans a run for their money, it’s going to have an impact on the way you hold yourself during your next black tie soirée.

A quality dress shirt will provide a solid foundation on which to build the rest of your eveningwear and so it’s not a purchase to be taken lightly. “It’s just a white shirt,” you might think. “How difficult can it be?” However, picking the right one out can take a masters in menswear because there’s a surprising amount to bear in mind if you want to elevate your black-tie attire from Dr No Idea to Double-0-Heaven.

To school you in the minutiae of this most troublesome formalwear component, we’ve prepared an in-depth guide, covering everything you ever wanted to know about dress shirts but were too afraid to ask. Starting with the basics…

What Is A Dress Shirt?

Just to make matters that little bit more confusing for you, definitions of the term ‘dress shirt’ will vary based on who you ask. Query an American, and he’ll tell you a dress shirt is anything with a collar and cuffs, that’s smart enough to be worn to the office. However, here in the UK, our definition is a little more specific than a work shirt, and for the purpose of this guide, that’s what we’re going to be talking about. Sorry, America.

First off, you certainly wouldn’t want to rock up to work sporting a dress shirt. Not unless you’re the Queen’s butler or one of those gents who holds the doors open at posh department stores. No, a dress shirt is to be worn exclusively as part of a black-tie outfit, most commonly a tuxedo.

“An evening shirt will ideally have a slight cutaway collar to make a space for the bow tie,” explains Jermyn Street master shirtmaker, Emma Willis. “[It should also feature] a super-imposed rounded or squared bib front either in a stiffer ‘marcella’ pique fabric or pleated for a more decorative look, holes for suds on the front rather than buttons …and a double cuff for cufflinks, which can match your studs.

“The ideal fabric for an evening shirt would be as light as possible for evening cool especially if you are dancing, [always in] white or ivory cotton or silk. The collar and cuffs look very sharp in the white marcella too if you are having this bib front.”

Man Wearing A Tuxedo And Cumberband

The Key Dress Shirt Components

Still with us? We never said it was going to be easy, but if you really want to wow the shop assistant with your shirting knowledge, it’s important to understand the three key elements that set dress shirts apart and how they can vary across the board.

Collar

One of the first things a newcomer is likely to notice about a dress shirt is the collar. Most often it will be a turndown collar. However, classic pointed collars and cutaway collars are also common. Save winged for white tie occasions.

Textured Tuxed With Shawl Collar

Cuffs

While casual and formal shirts tend to come with barrel cuffs fastened by a button, dress shirts do away with this in favour of a dressier French cuff, which doubles back on itself and is held in place with cufflinks.

Another more modern option is the cocktail cuff, which was invented by Turnbull and Asser for use in the James Bond classic Dr No. It features a turnback with a cutaway, allowing for buttons rather than cufflinks. All the good looks of a French cuff, without the fuss.

Turnback Cuffs And Cufflinks On A Dress Shirt

Bib

While we know it best as a tool to prevent babies from getting revolting-looking paste and vomit all over themselves, in the world of eveningwear, an altogether different type of bib is at work.

The dress bib is an additional layer of material commonly stitched into the front of a dress shirt. It tends to be either plain or pleated and gives a thicker appearance when worn under a jacket while allowing the body of the shirt to remain light and breathable.

Man Wearing A Dress Shirt And Bow Tie

How Should A Dress Shirt Fit?

Selecting a quality garment is half the battle, but if trying it on leaves you looking like either the a kid wearing his dad’s clothes, or the Hulk when he gets all green and angry and bursts out of his clothes, it will all have been for nothing. Ideally, you want to be aiming for somewhere directly in between those two extremes.

“A well-fitted, well-made shirt is always a must, but even more so when it comes to eveningwear,” says Dean Gomilsek-Cole, head of design at Jermyn Street master shirtmaker Turnbull & Asser.

“A loose fitting shirt will become uncomfortable with excess fabric folding, rucking and rubbing against the skin.

“While a shirt that is too tight can look good standing, but will also become uncomfortable when seated, and can lead to button strain, which is not a good look.”

In short, a good dress shirt should fit much the same as any other type of shirt – the main difference being the length. Dress shirts tend to be made significantly longer in the back and tails for tucking in, so don’t worry if you try one on and it looks like you’re wearing a nighty.

Aside from that, the shoulder seams should rest nicely on, well, your shoulders, the cuffs should be comfortable and shouldn’t extend onto your palm, while you should be able to fit two fingers between your neck and the collar when the front is done up.

What Material Should A Dress Shirt Be?

If you’re lucky enough never to have spent a sweaty afternoon at a black-tie summer wedding, you might think that shirt material is of little importance. However, once you’ve experienced the hell that is a dinner jacket/heavy twill combo in 30-degree heat, you’ll immediately get a sense of its significance.

“One tip from me for formal occasions is to get a bespoke dress shirt made from a voile cloth,” says Gomilsek-Cole. “This cloth is very lightweight and perfect for wearing under formal dress when you have to keep your jacket on for long periods of time.

“The fabric is quite transparent. But the trick is to have the front panel, collars and cuffs and front ‘bib’ made with a heavier cloth and no one will ever know how you managed to stay so cool and composed.”

Aside from voile, pique – sometimes referred to as ‘marcella’ – is the shirting material most commonly associated with the black tie dress code. It was initially created for use with white tie attire, as the way the fibres are woven makes it capable of holding more starch than other cotton fabrics.

Being nice and light, poplin is another good option in the warmer months, plus the smooth, silky appearance lends itself perfectly to a dressed-up look.

When To Wear A Dress Shirt

Easy. If the dress code says anything other than black or white tie, you should leave your dress shirt well alone. No one’s going to look good wearing a starched shirt with a pleated bib with a pair of jeans. While we’re all for individual style, there is a line and wearing a dress shirt with anything other than a tux crosses it by a country mile.

How To Wear A Dress Shirt With A Tuxedo

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The Best Brands For Dress Shirts

Now that you could give the experts on Jermyn Street a run for their money in a dress shirt-themed episode of Mastermind, let’s take a look at what you should be spending your money on.

Turnbull And Asser

If your end goal is to look like Bond then who better to buy your kit from than the people who dress him? Not only has the luxury London-based outfitter dressed 007, but it has also created shirts and accessories specifically for him, including the famous cocktail cuff.

Turnbull And Asser is steeped in history and has been held in esteem by some of the most important men in Britain and beyond. When it comes to quality and prestige, this Jermyn Street heavyweight is second to none.

Buy Now: £255.00

Turnbull And Asser Dress Shirt

Hawes & Curtis

Originally founded by London tailors Ralph Hawes and George Frederic “Freddie” Curtis in 1913, Hawes & Curtis quickly became known as one of the most respected gentleman’s outfitters in the capital.

The heritage label is the original Jermyn Street shirtmaker and has outfitted everyone from Hollywood stars to royalty during its time in the city.

Expect high quality, heaps of sophistication and price tags that won’t leave your wallet empty.

Buy Now: £79.00

Hawes & Curtis Dress Shirt

Next

Next is one of the most reliable names on the British high street and is well known for making slick suits at affordable prices. The brand’s sartorial output doesn’t end there but carries over nicely into the eveningwear arena.

You won’t get handcrafted, made-in-England garments, woven from the most beautiful silk cloth, but what you will get is a solid, stylish dress shirt and change from £50. Can’t argue with that in this stormy financial climate.

Buy Now: £24.00

Next Dress Shirt

Emma Willis

The first and only female shirtmaker to boast a shopfront on Jermyn Street, Emma Willis is widely regarded as one of the best in the game. The celebrated tailor counts the likes of Daniel Craig and David Gandy among her returning customers, and when you take a look at her masterfully crafted shirts, it’s not difficult to see why.

For stunning bespoke and ready-to-wear shirts, handmade with premium materials in London, you need look no further.

Buy Now: £350.00

Emma Willis Dress Shirt

Zara

Thanks in no small part to a highly responsive supply chain, Spanish high-street heavyweight Zara is always at the cutting edge of what’s fashionable. However, that’s not to say its timeless classics aren’t up to scratch, as exemplified perfectly in its range of sharp, crisp dress shirts.

Expect contemporary cuts, modern styling and prices so cheap you’ll feel like stocking up your entire evening wardrobe.

Buy Now: £19.99

Zara Dress Shirt

Marks And Spencer

A shirt bought from historic British retailer Marks And Spencer is a shirt bought with confidence. Renowned for its reliable quality, huge variety and timeless designs, it’s no wonder M&S has become a firm favourite in the UK.

If you’re looking for a sturdy, reliable dress shirt that you won’t need to sell a kidney to buy, you will find it right here. An ideal choice if you’re only pulling your tux on once or twice a year.

Buy Now: £45.00

Marks And Spencer Dress Shirt

T.M. Lewin

Established in 1898, T.M. Lewin is one of the most historic shirtmakers on Jermyn Street and unlike many of its neighbours, the prices are well within most budgets.

These modest price points aren’t indicative of subpar quality either, which goes a long way towards explaining why this heritage outfitter is one of the most popular in the country.

Buy Now: £49.95

T.M. Lewin Dress Shirt

Thomas Pink

Founded by Irish brothers James, Peter and John Mullen in 1984, Thomas Pink set out on a mission to challenge the traditional shirt making for which Jermyn Street had become famous. Named after the 18th-century tailor who designed the famous red hunting coat, the label carries on the name and tradition of exquisite attention to detail which was a hallmark of Pink’s work.

Choose a shirt from Thomas Pink and you’re buying into a focus on the more delicate details and a perfect blend of tradition-meets-modernity.

Buy Now: £100.00

Thomas Pink Dress Shirt

Charles Tyrwhitt

Nicholas Charles Tyrwhitt Wheeler founded his eponymous label in 1986 after deciding he could make a better shirt than anyone else. What’s more, he believed he could do it with no compromise on quality, a dash of British charm and at absolute knock-out prices.

Did he succeed? Well, judging by the fact that his business now boasts 27 successful stores worldwide, including a flagship on Jermyn Street, we’d say so, yeah.

Buy Now: £49.95

Charles Tyrwhitt Dress Shirt

John Lewis

Having opened the doors of its first store on Oxford Street in 1864, luxury department store chain John Lewis has gone on to become one of the most established names on the high street. The brand has a reputation for its unfaltering solidity, making it the first port of call for many a shopping Brit.

Regarding men’s eveningwear, it’s more of the same. Timeless, quality garments that offer a touch of luxury at not unreasonable prices.

Buy Now: £40.00

John Lewis Dress Shirt

For The Menswear Geeks: The History Of The Dress Shirt

Having first appeared on the shoulders of European men in the early sixteenth century, the shirt quickly went on to become the undergarment of choice. Just the ticket for keeping all that sweat away from expensive clothes at a time when personal hygiene was still a pretty abstract concept.

As the years rolled on, a crisp white shirt became a status symbol, as only very wealthy men could afford to keep them pristine. Then, during the Victorian era, and with the rise of the dinner jacket, the dress shirt, as we know it today, was born.

Unlike in the thicker, more substantial shirts of years gone by, shirtmakers began to manufacture shirts with a bib panel stitched onto the chest. This panel could be starched, giving the front of the garment a whiter, crisper appearance, while reducing the thickness of the shirt overall and maximising comfort.

After World War II, the tuxedo became de facto eveningwear, cementing the modern dress shirt as one of the essential components in today’s black-tie attire.