I feel that I should start this article by stating for the record that this is merely a list of suggestions or guide for those in need of some inspiration or reassurance. As always, how you should dress should always be about comfort and confidence. My biggest advice when it comes to style is wearing what YOU feel comfortable in, don’t be afraid to express yourself. Style insecurity should be confined to your late teens and early twenties as you discover who you are and what you like. By the time you hit the half century mark, you have earnt the right to wear whatever you want and don’t let anyone tell you otherwise.

However, for those facing a midlife fashion crisis, I have concocted this simple guide designed to help ensure you tick all the right style boxes.

Essentially your wardrobe in your 50s should be pretty similar to your 40s with a focus on fit and colours rather than trends. Making sure your clothes fit right is key. Go through your existing arsenal and make sure all of it slips on easily. Anything that requires lubricant or an assistant to help you ‘get into’ or ‘zip up’ should be binned. You want to feel comfortable for whatever situation you are dressing for.

And whilst the more ‘extravagant’ elements of casual wear might be harder to get right, there is no reason to assume that the only way you’ll look good is in a suit. Yes, your wardrobe should lean far more on the side of classic, timeless style than fleeting fashion by now, but there is no need to dismiss the catwalk altogether - there are still plenty of items that are going to work for you. However, rather than going to the trend-heavy brands, make the great suit makers of London and New York your starting point. Tom Ford, Ralph Lauren, Richard James amongst others are always a great source of inspiration for those looking for a more classic style.

One word of advice: Casual shoes or trainer become increasingly difficult to pull off as you verge into the late 50s - especially the brightly coloured or heavily branded variety. Instead, invest in an enviable array of smarter shoes that are still comfortable. Loafers, monk straps and Chelsea boots in a selection of colours would be a great start. Driving shoes, deck shoes and smart suede espadrilles can also be the perfect alternative for a more casual look. If you do opt for a trainer, stick to sleek classic designs in block colours. A pair of Adidas Stan Smiths or Fred Perrys is a safe yet highly stylish option when it comes to your trainer collection.

5 golden rules of how to dress in your 50s

Brad - 53

George - 56

Colin - 56

1. Block colour

Now there is no need to remove colour altogether from your wardrobe. But, you will want to start removing anything too shiny, metallic or bright and instead look more towards earthy organic tones. Browns, forest greens, light grey and navy blues are a safe bet. It is also worth investing in a few pieces in complimentary colours that you can mix and match together.

2. Treat yourself

Up to now, you may have thought twice about splashing out on that Gucci jacket or Prada briefcase. You should use your 50s as a time to treat yourself, spend a bit more and invest in items that will last. Again keeping it classic will ensure it still looks great in years to come.

3. Update your suit collection.

Drainpipe suits with slim lapels are no longer the way forward. If you have any left in your wardrobe, now’s the time to filter them out and replace them with something to suit a more mature body shape. If in doubt, go for a trim, two-button jacket with wider lapels and well-tailored, flat-fronted trousers.

4. Accessories

Keep your details subtle by avoiding big logos and look for a more sophisticated style. Anything too brash will scream midlife crisis and you want accessories that will enhance and recognise your style, not your spending power.

5. Don’t panic

Some men panic when they hit this halfway birthday.

Stop. Whether you’re single or have been married for twenty years, that old adage about men getting better looking with age is true - and you should be taking advantage of it whenever you can. Positivity and confidence are attractive qualities in a man. Trust me - a confident you in your 50s is an improvement on that shy, ignorant twenty something you look back on with envy.


“God is in the details, so now invest in the best quality accessories that you can afford. They will literally last a lifetime. Also remember that feet don’t get fat and a watch will always speak volumes.” Robert Johnston, GQ Style Director