To be considered well-dressed, you always need to put your best foot forward. I wrote before that it’s a way of life you need to commit to: from trips to the tailors to looking at different pieces and outfits for inspiration, it’s more than a case of throwing some clothes on in the morning. If you haven’t already, check out my previous post about how to start building a stylish wardrobe. You can find it here.

There are several pitfalls men make when dressing. I know because I've made some of them myself when I was younger, particularly cheap shoes. I once bought a pair of very nice suede loafers from Zara for around £65. They never fully broke in. The leather was so cheap and stiff that even after a dozen-or-so wears, they still gave me blisters. I donated them to charity and purchased a pair of Magnanni loafers. Aside from being several classes above, after one or two wears they felt like carpet slippers.

The following are what I think are 5 common style mistakes that should be avoided.

• Wearing ill-fitting clothing

A man with baggy trousers or sleeves that are too long will never be considered well-dressed, it just looks untidy. Find yourself a good tailor. I use two, one for simple alterations like shirtsleeve shortening, trouser hemming/tapering and another for shortening my blazers sleeves from the shoulder crown. To have shirtsleeves shortened should cost around £12 and trouser hemming around £6. For a relatively small outlay, it will transform your appearance.

• Wearing bad or cheap shoes

I’ve seen many a man that have got the fundamentals of an outfit correct: jacket fits well, trousers are a good length, their tie compliments their suit only to completely let themselves down when it comes to their choice in footwear. Opt for a classic derby or oxford with an almond toe from a good shoe-maker: Crockett and Jones and Joseph Cheaney make very good shoes although they’re not cheap. For decent shoes at a lower price point, Meermin and Loake are two good options. Remember to clean and polish them too. Apart from elongating their lifespan, scuffed and battered shoes can ruin an otherwise good outfit, making you appear careless.

• Trying too hard

Overcoats worn with cargo trousers, wearing a cape, matching ties exactly to their pocket squares, 22 competing accessories- some men try far too hard to dress stylishly or to stand out. It should only be visible how well you are dressed on the second glance. If people are turning to look at your outfit, you’ve got it wrong. Keep it simple and keep it classic. If you’ve nailed the fit, the compliments will come.

• Putting too much in your pockets

So, you’ve been to the tailors and your trousers have been hemmed, tapered and they’re sitting on your tasteful, well-polished shoes beautifully. There is however the problem that you’ve jammed your wallet, phone, keys, cigarettes etc., into your pockets, leaving unsightly bumps at the top of your thighs. Invest in a slim-line card holder for some cash and necessary cards, then pick up a nice leather portfolio for keeping your keys and any other necessities in i.e., books, tablets etc. The bumps have gone and you’ll find your ease of movement has improved tenfold. Not to mention how much more comfortable you’ll be when seated.

• Forgetting about style in the heat

It seems that when the temperature creeps up above 20° men lose all sense of style and propriety. Shorts outside of the beach or poolside are rarely a good look. I’ve even seen a man wear shorts to the theatre. In January. As Tom Ford said “A man should never wear shorts in the city. Flip-flops and shorts in the city are never appropriate. Shorts should only be worn on the tennis court or on the beach”.

Likewise, sleeveless tops are best reserved for the gym. Instead, opt for trousers and shirts in lightweight fabrics like linen and cotton/silk/wool-linen blends. Linen allows the garment to breathe, is excellent at wicking sweat and will lend you an air of rakishness. Don’t forget to iron it though: linen may crease naturally but there’s a big difference between artfully dishevelled and creased to death.

If you can manage to avoid these styling pitfalls, you’ll be on your way to being better dressed in no time. These are common style mistakes that I frequently see and the ones that annoy me the most but there are certainly many more. What are your styling pet peeves? Let me know below. Finally, for bonus points, why have I chosen the header image to illustrate style mistakes? Answers below please.

Thanks for reading,
Terry