Dressing well is an art. From your clothes to accessories, there are many ways you can elevate your overall appearance. Not only does a well-curated wardrobe help you look fantastic, but it can also boost your confidence. If you’re trying to upgrade your attire, but you’re not sure where to start, don’t stress. Here are some tips on how to dress well to help you update your outfits, and feel amazing all at once!
1. Wear A Suit Well
The key to a suit looking good is fit. If you’re buying off-the-peg, focus on the fit across the shoulders because getting the chest and waist altered is a relatively easy job according to Davide Taub, head of bespoke suits at Savile Row tailor Gieves & Hawkes. “Be cautious about wearing a period suit unless you’re pursuing a total period look because in isolation the suit starts to look like a novelty,” he adds. Classic is the best and most useful – dark, two-button, single-breasted, moderate in detail. “It’s not boring. A suit is a uniform. The idea is to think of this suit as a canvas to build different ideas of individuality around. It’s the way you wear it, not the label inside, that impresses.”
2. Invest Wisely In A Watch
“A watch is like a piece of art,” argues Don Cochrane, managing director of British watch brand Vertex. “Choose it because you love it, not because you think it might make money. Watches are personal, it marks your passage through time. But you also have to be practical.” Aesthetic, functional, rugged sports models go with anything and can take the hard knocks of everyday wear. Yet, a watch still has to fit you. It should feel comfortable and be right in terms of size and depth relative to your wrist as well – 40mm is considered the ‘Goldilocks’ size.
3. Don’t Shy Away From Colour
Whether it’s on casualwear or formalwear, indulge in a bit of colour. “Most men are unjustly scared of it – they’re intimidated by anything that isn’t navy or grey,” says menswear designer Oliver Spencer. “But the colour can be timeless too.” A green suit, for example, can look particularly rakish, while Spencer also recommends pinks, greens, mustard and brighter shades of blue as especially versatile year-round shades that will lift your entire outfit. But he adds that, when it comes to colour, less is still more: “You just need a bit of it, in one garment.”
4. Wear In Your Jeans Until They Are Yours
The all-time most useful cut of the world’s most popular garment, according to Alex Mir, co-owner of Sheffield-based label Forge Denim, is ‘slim-tapered’. “It’s wider in the thigh, so it’s comfortable, but narrows, so it works with either smart shoes or sneakers,” he advises. “It’s the best year-round, wear-with-anything, dress up or down style.” The wise will wear dark, raw denim too and give the pre-distressed a wide berth. “The whole pleasure of denim is that it ages with the way you wear it. Why miss out on that?”
5. Spend Money On Shoes
“Timelessness is about simple design and all the more so with shoes,” argues Tim Little, owner of heritage shoe brand Grenson. “The colour, the pattern, the sole – you don’t want it fussy. Anything fussy may look good now but will look strange very quickly.” Quality shoes — the gold standard being re-soleable Goodyear welted examples — are the kind of investment that should last 15 years or more. Opt for classic styles such as brogues, loafers, or a plain, dark, five-eyelet Derby on a round-toe last. “It’s the shape of the toe that really counts – and round never goes out of fashion,” says Little. “It’s pointy toes or square toes that look obviously impractical. Nobody has feet shaped like that.”
6. Keep Accessorising To A Minimum
Accessories like ties and pocket squares bring individuality to classic clothing, but be careful how you use them. “It’s best to harmonise them with what you’re wearing by picking out a colour or two. Or even to juxtapose them entirely,” says Michael Hill, creative director of men’s accessories brand Drake’s. “What you don’t want is to match them up.” When it comes to curating shirt and tie combinations, wear your tie or pocket square in a darker shade than your jacket. And don’t overdo the accessories either – if in doubt, think less is more and take one element away. “You’re aiming for an air of nonchalance,” adds Hill. “You just need one point of interest.”
7. Dress For The Setting
Style is not merely about self-expression; it’s also about being dressed appropriately for your environment. Think of clothes as being codes: you need the right combination to work with the setting you’re in – and that’s whether it’s a formal dinner or a lazy Sunday in the pub. The worst style is one which is out of place. Is this a kind of conformity? No, as one of Tom Ford’s oft trotted out fashion quotes explains, it’s a mark of respect for others. And about feeling comfortable in yourself. When in doubt, overdress.
8. Don’t Skimp On Glasses
Invest time in finding the right spectacles for you. “People spend an average of seven minutes picking a pair that will define them for the next three or more years,” notes eyewear designer Tom Davies. “Poor choice and poor fit are why so many people learn to hate their glasses.” Buy what you feel good in, taking into account your face shape but considering the top line of the frames’ relation to your eyebrow shape – team straight with straight, curved with curved – and your hairstyle. Buy wisely too, says Davies: there’s no point buying cheap frames and being up-sold on expensive lenses because the frames will look tatty soon enough anyway.
9. Choose Versatile Outerwear
The temptation may be to wear a classic style, but modern technical fabrics in darker shades and easy cuts are making coats what they should be – lightweight and breathable but also properly protective. “Changes in seasonality, the climate and buying habits are making heavy wool coats seem out of keeping now,” suggests Adam Cameron, owner of outerwear specialist The Workers’ Club. “Think of a coat instead as being your final layer – one you can wear as much or as little under as required.” A field or bomber jacket is a good all-rounder but if you need to dress up, go for a short mac.
10. With Shirts, Stick To The Classics
“It sounds silly,” says James Cook, head of bespoke shirtmaking for Turnbull & Asser, “but any men’s shirt can be made to look expensive if it’s well-pressed.” All the same, Cook is particular about the details. Strike a middle line, he recommends: avoid bold styles unless you think you can carry it off, and, for a collar that works with or without a tie, and that always sits properly under a jacket, opt for a semi-cutaway.