How to dress in your 20s

Because those first steps into adulthood should be made in impeccable style

Oliver Cheshire shot by Adam Fussell for Gentleman's Journal black and white
Photo by Adam Fussell for Gentleman's Journal

It’s safe to say that your twenties can be, at times, a difficult decade. From student loans to starting a career, you’re not alone – and will probably find that the questions just keep coming. From the classic ‘what do I want my career to be?‘, and ‘who should I vote for?’, to the more leisurely ‘where should I travel next?‘ and ‘when should I start dressing properly?’

But the fact is, whatever style you settle for now will probably influence and come to typify your everyday image well into your 30s and beyond. So, for those of you who simply reach for a hoody and pair of jeans every morning, shame on you. As twenty-somethings, we are the next generation – and we must set an example in everything from our attitude to politics to sartorial style. So be responsible, fashionable, invest wisely and be resourceful with what you buy.

Douglas Booth, John Boyega, Aaron Taylor Johnson, Ollie Cheshire and Tinie Tempah
From left: Douglas Booth 24, John Boyega 25, Aaron Taylor Johnson 26, Ollie Cheshire 28 and Tinie Tempah 28

These are the qualities that will not only determine consistent style, but also help you become a more interesting man. So begin asking yourself; ‘what are the major problems in this world today, and how do I tackle them?’ – and then proceed to apply this same outlook to the small matter of your style.

Not investing for the future is one of the biggest bad habits of 20-somethings, and we’re not just talking about draining your savings account. When it comes to your wardrobe, try planning ahead realistically (no more than a year, because things do change) and be sensible about the purchases you make today – so your future self will thank you dearly.

It's more acceptable to hop around in your 20s, than in your 30s - to learn the lessons along the way

But, at the same time, don’t be afraid of taking the trial-and-error route – it’s the only decade in your life where you can get away with being changeable with your career choice (and relationships). It’s more acceptable to hop around in your 20s and learn the lessons along the way, but not in your 30s. Your aim for your 20s should be assessing what skills are worth honing, and then fine-tuning them.

So, gentlemen, by all means experiment with trends and clothing while you still can, but be cautious with the style foundations you build now, as this crucial decade will make or break your many decades of adulthood to come…

Keep things fresh - and personal

You’re in your 20s, so make the most of it. Dauntingly, there’s plenty of time to dress like your father, so there’s really no excuse to be fuddy-duddy with your style – unless you really do come from a cardiganned and corduroy land that time forgot.

Tinie Tempah by Gary Houlder for Gentleman's Journal

It does pay to be aware of what’s trending on the streets, because whilst the classic suit and pair of Oxfords will forever be wardrobe staples (and essential to your post-grad job), switching up your shoe game with trendy trainers will gain the approval of your fellow millennial group. Still not convinced with street style? You should be, because it’s what constantly defines the style of today.

The Bomber Jacket: There’s no doubting that the bomber jacket has seen a recent revival, risen from the ashes of the 1980s and 90s. And, with the 20-somethings of today, such as Tinie Tempah, 28, now paying homage to their birth decade, there are bombers hanging in wardrobes the length and breadth of Britain. A super-versatile jacket, this icon pairs well with a t-shirt or jumper, and its cropped length is a welcomed feature for those who may not be blessed with the tall gene, since it makes your legs appear longer.

J Crew Bomber

The Denim Shirt: It’s a no brainer why this happens to be Tinie Tempah’s favourite go-to shirt. It’s a wardrobe classic that sits perfectly alongside your Oxford button-downs and white t-shirts. And, since they’ve now become immune to trends, we advise to invest now, and wear for many years to come.

How to dress in your 20s

The Backpack: Who remembers back in the day, when your school bag determined your level of cool? Now, in your 20s, we’d like to think our social sensibilities have matured somewhat – but they probably haven’t. Investing in a cool backpack will make you aware of the design’s convenience and make your look cool – you’re handsfree and can carry a lot more weight on your shoulders than say, a tote.

Herschel black backpack

The Trainer: Okay, these may be worn by people of almost any age, but if you haven’t invested in a quality pair of trainers, what are you waiting for? Since you were born in the late 20th century, you should also know that some of the most iconic gentlemen of that century had seriously strong shoe game – Steve McQueen and James Dean for instance. Start with a white pair that’re clean on the lines, and preferably crafted from either leather or suede. What’s more, the humble white trainer can be worn all year round.

Saint Laurent trainers
Adidas Stan Smith men's triple white

Learn the sartorial lingo

Do you know your pinpoints from your poplins? Perhaps your Prince of Wales check to the Prince Albert knot? No? Well, this is the decade where you’ll learn more than ever before – from academia to sartoria. And all of this education will prove crucial in transforming yourself from a man to a gentleman. Take inspiration from Ollie Cheshire, 28, who pulls off just the right amount of sartorial sophistication, without dressing beyond his age.

Ollie Cheshire by Adam Fussell for GJ
Photo by Adam Fussell for Gentleman's Journal

Granted, not everyone will speak the language of Savile Row, and Jermyn Street, but knowing how to invest in quality formalwear is a surefire way to help you secure that promotion, or land a job to kick-start your career.

Steer clear of poly-blend, ill-fitting, poorly-constructed suits - at all costs

Our advice? Invest in a quality Jermyn Street shirt where detail and craftsmanship will ensure each layer looks the part, and lasts. What’s more, a select number of shirt makers now include non-iron options (which make that morning rush a little easier). Wearing a Jermyn Street shirt is another way of you saying; “I’m to be taken seriously, I know what good taste is, and I’m well-mannered enough to interview with you in appropriate style.”

When it comes to suits, going bespoke is not your priority at this stage in life – that luxury will come in good time. But steer clear of poly-blend, ill-fitting, poorly-constructed suits – at all costs. You’re not a teen anymore. You’re an adult; so dress like it.

The Suit: There’s no denying that you’ll have interviews lined up, wedding invitations trickling in and suave networking events to attend, so it really pays to invest in a proper suit. Whether it’s a two-buttoned classic, or a double-breasted power suit, make sure you steer clear from single-vented jackets when possible, and instead opt for a double-vented jacket as your wardrobe mainstay.

How to dress in your 20s

The White Shirt: On many occasions, the difference between a man and a gentleman can be whittled down to his shirt. One will sport a flimsy-collared cotton-blend shirt with no split yoke, whilst the other will be wearing a well-constructed Jermyn Street offering, with collar stiffeners, a split yolk and mitred cuffs.

If you’re perplexed with the above terms, it’s worth visiting an established Jermyn Street shirtmaker, after which you’ll appreciate why such impeccable shirts are priced so highly. The cost reflects the craftsmanship and, in turn, reflects the man you want to be. Your first quality shirt should be a white button-cuff option, with a semi-cutaway collar, as worn by Aaron Taylor Johnson, 26.

How to dress in your 20s

The Oxford ShoeUltimately, classic Oxfords are the simplest, smartest pair of shoes you’ll ever need. Purchasing a first quality pair in black will guarantee many wears with any suit, and any formal occasion. Don’t fall victim of standing out like a sore thumb with rubber-soled alternatives. You can talk the talk, so walk the walk, too.

Oliver Sweeney Leadenhall Oxford shoes

If in doubt, accessorise wisely

Given that your 20s involve a lot of learning, ups and downs and everything in between, there is an easy way to sartorially survive this decade. Invest in one single accessory that you’ll wear with everything – yes, everything.

How to dress in your 20s

Whether it’s a watch or cuff, you’ll be greatly admired, and remembered, for wearing one signature accessory that shows consistency in your style, and – more importantly – your personality.

The Cuff: Whilst the question as to whether men should wear jewellery other than their wedding ring will forever be debated, a timeless cuff bracelet is not only stylish and masculine, but you’ll have a hard time finding a reason to take it off.

How to dress in your 20s

The WatchThis will forever be every gentleman’s favourite accessory, so it only makes sense to wear a classic watch that stays refined no matter what you wear. A quality watch needn’t cost you thousands (unless it was gifted to you, or you happen to have a taste for high-end Swiss movements), but should certainly be expensive enough to see you through any outfit, day and night.

Tag Heur Aqua Racer

Further Reading