You would think that dressing well is a skill that, once mastered, it’s retained for a lifetime. Dressing well is like any other skill set, which over time needs practice, revision and continuous relearning. The logo t-shirts you wore in your university years will not be making the same statement in the corridors of your university as they would do in the corridors of your employer. The skinny fit jeans you wore in your twenties with aplomb will scream mid-life crisis in your forties.

On the other hand, it’s important not to jump the gun and relegate yourself to a life of drab attire. At any age, the key is to strike a balance. Over the next few day’s I’m going to go through the decades and discuss what I think are key considerations for us men as we go through life

So let’s get’s started with the……

The Twenties

Now the twenties in by gone eras signified a coming of age in life. This is the decade our fathers bought a house, got a steady job and, if they were really serious about growing up, became a parent. Now, of course, it’s a confused, mystically extended adolescence, in which it’s never quite clear whether we’re supposed to be responsible or having fun? This leads to a sartorial limbo. What is clear is that we’re grown men in this decade, and the key to mastering how to dress in your 20s can be summed in two words: capsule wardrobe.

This is the time to invest in important go-to pieces that will form the foundation of your wardrobe for many years to come: hard-wearing chinos, jeans, smart shoes, a proper suit and a decent watch.

It’s also a good time to experiment with trends, and yes you’ll make mistakes with fits, colours, patterns but we’re young – now’s the time to do it and work out what looks good on you.

As you reach the end of the decade, it’s time to invest in your first designer pieces. I’d recommend starting with small bits which are nice finishing touch bits of detail: ties, cufflinks or wallets, and your work your way up as your budget expands with your age.

The rules of how to dress in your twenties:

1) Slim cuts

Not skinny fits! We’re in the best shape of our lives, your metabolism is that an all time high, you don’t need to spend hours in gym to maintain it. So make the most of it by searching out clothes with slimcut but don’t swamp you in acres of excess material.

2) Know your colour

As a general rule, like colours work best on dark skin (pale blue, yellow, pastel pink, white) and darker colours work best on light skin (maybe blue, dark green, dark red, brown). When you decided on which you feel most comfortable win, adopt it as the backbone of your accessories game. If you invest in stocks, pocket squares and toys that are both solid and have hints of the colour in a pattern, you have created a interchangeable selection.

3) Experiment 

Need to make the most of this decade by trying out different patterns and more tread-led items that can be added into your core wardrobe as the seasons change.

4) Your barber is your friend 

Never underestimate the power of a good haircut! Get to know your barber and they will keep you looking good for years to come.

5) Look after your shoes 

The 20s are a decade where making the right first impression counts, whether that be going on a job interview or getting out there on the dating scene. It’s often said that shoes are the first thing a person notices about your outfit, either consciously or subconsciously, are you all shoes – so they better be clean and shiny. Make sure to regularly polish your shoes and also look after your sneakers.

Essential items for the twenties

  • White shirts – stock up with a mixture of former collars preferably semi-cutaway with removable bones and button-downs and make sure there’s always a few hanging in your wardrobe.
  • First proper suit – select a suit that is going to cover you for weddings, interviews, work and any other occasions you might need it for. I would suggest always sticking with a plain deep navy which will allow for greater versatility in use. Always check the weight of the fabric preferably going for a walk cotton mix that will enable you to wear the suits in summer the shirt but can also be laid with a jumper or a coat in winter. I would highly recommend always having an extra £50 in your budget to have it tailored to your physique.
  • Watch – it’s worth getting a smart watch that goes with everything you own, ideally stick with a metallic strap.
  • Jeans – without a doubt you’ll wear your jeans more than any other item in your wardrobe, so it’s definitely worth investing a little more than we normally have done in a good pair of jeans. It’s certainly worth getting the fit right so identify a couple of brands and stick to them. In terms of washes for me you always need a dark or mid-indigo wash, a solid black wash and a stone wash.
  • Leather jacket – not just for gigs or concerts. The right leather jacket can be utilised crossed seasonal as a statement piece in spring/summer or as a added peace of layering in winter.
  • Formal shoes – every man needs a minimum of two pairs of formal shoes in their wardrobe, one black and one brown. If you have a bit of money left over it’s worth investing in a pair of Chelsea boots (refer to my post from a few weeks ago Chelsea (Re) Boot).

Throw away before you hit thirty:

  • Deep V-neck T-shirts
  • Novelty pants or socks
  • Flip-flops (for the beach only)


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