Fashion is – at heart – about the tension between rules and creativity. The blossoming of ideas on a handful of catwalks which quickly coalesce into a diktat.

It’s a cycle accelerated by the high street – Zara can turn product from design to store in about a month – which means rules cement faster, but are also more quickly knocked down. And it can be an exhausting thing to keep abreast of.

Which is why it’s useful to mark the distinction between fashion and style. The former is the effervescent trends that rise, burst and dissipate season-to-season: florals in, florals out; navy everything – no, azure – now cyan (do keep up). Things you can take a punt on and, if you miss, the only discernible damage is a few embarrassing Facebook photos.

But toying with trends is for nothing if you’re making more fundamental errors. As the lauded late French designer Yves Saint Laurent put it: “Fashion fades, style is eternal”. Which is true, although ascertaining how to attain that timelessness is trickier. Quiz designers on their definition and they’ll each spout something nebulous about dressing to be the essence of yourself which, while an attractive idea, is little help facing down a bulging wardrobe.

So, we tracked down some of the most stylish men in the industry for the mistakes they see men make on a daily basis, and wish that they could fix. Because if you’re guilty of these sartorial faux pas, wearing camo a season too late is the least of your worries. Learn how to nail these and your style is sussed. Fashion, you can take or leave.

Daniel Todd, Buyer At Mr Porter

“Skinny jeans are a trend I thought might die out naturally, but unlike the indie explosion that brought it back, this one refuses to go away. I don’t hate all skinny jeans – and I’m not suggesting everyone switches to a grey marl jogger – but it’s about dressing for your body shape.

“Sadly, skinny jeans aren’t the male equivalent of Spanx. If you catch yourself thinking ‘I’ll just undo a couple of buttons when I sit at my desk’, they’re too tight.

“With a looser pant being presented at a lot of spring/summer 2016 shows, the general move to a more relaxed skate-style trouser was strong so hopefully this time the ‘death of the skinny jean’ isn’t a false dawn. For everyone’s sake.”

Fix It

If your legs are more tree trunk than twig-like, chances are skinny jeans won’t do you much justice. Instead, try a tapered slim cut or straight leg jeans for a roomier alternative that won’t cut off your circulation.

The same goes for your chinos and trouser collections.

gucci resort ss15j crew aw14reiss 2012bally ss15burton aw15tommy hilfiger summer 2014club monaco summer 2014burton aw15farah ss14selected homme aw14debenhams ss15jigsaw ss14

Key Styles

  • Acne Studios Town Slim-fit Stretch-denim JeansAcne Studios Town Slim-fit Stretch-denim Jeans
  • Nudie Jeans Steady Eddie Regular-fit Organic Dry-denim JeansNudie Jeans Steady Eddie Regular-fit Organic Dry-denim Jeans
  • A.p.c. New Standard Regular-fit Dry Selvedge Denim JeansA.p.c. New Standard Regular-fit Dry Selvedge Denim Jeans
  • Hackett Newburg Slim-fit Washed-denim JeansHackett Newburg Slim-fit Washed-denim Jeans
  • Levis 501 Ct Jeans 501 Ct Slim-fit JeansLevis 501 Ct Jeans 501 Ct Slim-fit Jeans
  • Officine Generale Slim-fit Washed-denim JeansOfficine Generale Slim-fit Washed-denim Jeans
  • Reiss Falls Slim-fit Raw Jeans IndigoReiss Falls Slim-fit Raw Jeans Indigo
  • Ted Baker T For Tall Dayton Regular Straight Jeans Rinse DenimTed Baker T For Tall Dayton Regular Straight Jeans Rinse Denim
  • Uniqlo Men Slim Fit Straight Stretch Selvedge JeansUniqlo Men Slim Fit Straight Stretch Selvedge Jeans

Damien Paul, Head Of Menswear At

“I’m always incredulous at the number of guys I see who have clearly invested in a really great suit, only to let it down with scuffed up shoes – invariably with a pointed toe. Bin them immediately, and invest in a pair of lace-up brogues or Derby shoes in quality leather. Tod’s, Church’s or Campanile should be your first ports of call.

“Just as bad is bringing your beach shoes home. On holiday, I’m a committed flip-flop wearer. But they have no place in a busy city – they’ll constantly be kicked off your feet by other commuters and you’ll end up with dirty soles and bruised toes. Not to mention the incessant flapping noise they make as you walk.

“For off-duty summer footwear, I’d recommend an espadrille – they look much more grown-up and are more robust. British brand Mulo is one to look out for – especially their pleasingly coloured suede styles.”

Fix It

As Paul notes, there’s little sense in investing in top-notch tailoring if your shoes are subpar. A pair of quality leather brogues, Derbies or Oxfords is a must for men serious about style.

When it comes to summer footwear, espadrilles are not only breathable, lightweight and practical in the heat, but also infinitely more sophisticated that a pair of flip-flops, whether you’re on the beach or pounding the city streets.

Men's Smart Leather Brogues, Oxfords and Derbies with Suits / Plus Espadrilles In Summer Outfits

house of fraser aw15boss hugo boss ss15sarar ss15m&s aw15tommy hilfiger tailored ss14thom sweeney ss15gant rugger ss15massimo dutti 2015mango man summer 2015lbm 1911 ss13pull & bear heritage ss13gieves & hawkes ss14

Key Styles

  • Tods Lace-up Derby ShoesTods Lace-up Derby Shoes
  • Campanile Lace-up Leather Oxford ShoesCampanile Lace-up Leather Oxford Shoes
  • Tods Lace-up Derby ShoesTods Lace-up Derby Shoes
  • Mulo Suede Slip-on EspadrillesMulo Suede Slip-on Espadrilles
  • Mulo Suede Slip-on EspadrillesMulo Suede Slip-on Espadrilles
  • Mulo Suede Slip-on EspadrillesMulo Suede Slip-on Espadrilles
  • George Cleverley Reuben Burnished-leather Oxford BroguesGeorge Cleverley Reuben Burnished-leather Oxford Brogues
  • Churchs New York Leather BroguesChurchs New York Leather Brogues
  • Edward Green Chelsea Burnished-leather Oxford ShoesEdward Green Chelsea Burnished-leather Oxford Shoes
  • Rivieras Cotton Mesh Slip-on ShoesRivieras Cotton Mesh Slip-on Shoes
  • Kin By John Lewis Contrast Trim Espadrilles NaturalKin By John Lewis Contrast Trim Espadrilles Natural
  • Castaner Pablo Perforated-leather EspadrillesCastaner Pablo Perforated-leather Espadrilles

Simon Crompton, Tailoring Expert And Founder Of Permanent Style

“Suit jackets just don’t work with jeans. It’s about the cloth (which is too smooth) and the styling (which is too formal) but it all adds up to a mess. Suit jackets need to remain – 99 per cent of the time – suit jackets.

“Equally bad is doing up the bottom button on a jacket. On a two-button jacket, do up the top one only. On a three-button, the middle and perhaps the top. If you can’t figure out a one-button jacket, then there’s something wrong with you.

“Also frustrating is when men don’t remove the basting thread on jacket vents. You know the little cross of thread that keeps your vents together on the back of your jacket? You’re meant to take them off. Otherwise it’s not a vent – it’s some sort of bizarre, fragile slit.”

Fix Tt

Want to pair a blazer with your jeans? The key is to pick the right style: steer clear of traditional suit jackets, which are often far too formal, and instead of opt for an unstructured sports coat, rugged tweed blazer, or equally relaxed design.

Then, combine with slim, plain denim to produce a perfectly balanced smart-casual look.

Men's Blazers with Jeans Outfit Inspiration Lookbook

austin reed ss15m&s ss14lbm 1911 ss15mac denim ss14j crew 2015banana republic pre aw14avva aw14Brunello Cucinelli ss16Beyene 2014

Tommy Cunliffe, Barber At Ruffians Barbers

“You need to be realistic about what haircut is going to work. Not everyone can achieve their desired look, unfortunately. A slick-back style doesn’t look great with curly hair and if you’re receding or thinning, don’t try a quiff or long hair.

“Speak to your barber about what’s a good look for your hair type and face shape. Then they can suggest something that takes into account what you like, what looks good for your angles and hair type, and what can be styled well bearing in mind your style and lifestyle.”

Fix It

Consultation is key to bettering your chances of getting an on-point haircut. Your barber or stylist should take adequate time to listen to your tastes and needs before getting to work – if they don’t, then don’t hang around.

Ruffians BarbershopImage: Ruffians

Dan Rookwood, US Editor At Mr Porter

“When some men first get into style, they really go for the whole ‘Pitti Peacock’ look and it’s all a bit much. You don’t need the bracelets, pocket square, tie clip and brightly coloured socks all in one look, it’s overkill.

“I am a firm believer in ‘less is more’ and the Coco Chanel maxim: ‘Before you leave the house, look in the mirror and take one thing off.'”

Fix It

There’s a lot to be said for staying understated. Although accessorising is essential in developing standout style, take care not to overdo it so as not to stand out for all the wrong reasons.

It's time to leave the Pitti peacock look behindIt’s time to leave the Pitti peacock look behind

Adam Brady, Marketing & PR At Ruffians Barbers

“Avoid bad skincare products. They can make you look shiny, or can give you strange reactions. A lot of big brand products use parabens and sulfates which are not only harmful to the environment, but can also irritate skin. Chemical preservatives may also contain alcohol-based molecules which can dry out the skin and cause flaking.

“Instead, you need alcohol-free products with natural ingredients. They’re better for your face, which is sensitive as it’s always open to the elements. And presumably gets shaved every now and then.”

Fix It

Much like hair, your skin is one aspect of your appearance you don’t want to skimp on. Try swapping big-name brands that spend heavily on marketing but are slack in the quality stakes for those who use naturally derived ingredients, like Aveda, Bulldog and, of course, Ruffians.

  • Ruffians Daily Facial MoisturiserDaily Facial Moisturiser
  • Ruffians Daily Facial ScrubDaily Facial Scrub
  • Ruffians Sandalwood Shaving GelSandalwood Shaving Gel
  • Bulldog Original Moisturiser 100mlBulldog Original Moisturiser 100ml
  • Bulldog Original Face Scrub 100mlBulldog Original Face Scrub 100ml
  • Bulldog Sensitive Face Wash 150mlBulldog Sensitive Face Wash 150ml
  • Kiehls Facial Fuel Energising Scrub 100mlKiehls Facial Fuel Energising Scrub 100ml
  • Kiehls Facial Fuel Energising Face Wash 250mlKiehls Facial Fuel Energising Face Wash 250ml
  • Kiehls Facial Fuel Moisturiser 125mlKiehls Facial Fuel Moisturiser 125ml

Karlmond Tang, Photographer & Founder Of

“Light wash straight-fit jeans, or jeans that are too long with cut-up cuffs, draping over smart black lace-up shoes such as Oxfords. It just seems like someone told you to wear smart shoes for the club on a Friday night or you won’t get in, so you put on whatever you were wearing and slipped on your old school shoes.

“Instead, go for a darker wash and wear jeans that fit properly if you really want to wear them with smart shoes. Ideally, avoid Oxfords – they tend to work best with suits.”

Fix It

Teaming jeans with smart shoes can be tricky. As Tang points out, darker colours of denim like indigo and black work better for dressed up looks.

They should also be cut slim or have a slight taper with a leg opening that’s narrow enough not to spill sloppily over your shoes. Speaking of which, Derbies, loafers, brogues or Chelsea boots work best in this instance.

Men's Jeans With Shoes Outfit Inspiration Lookbook

massimo dutti 2015suitsupply ss15sarar ss14massimo dutti equestrian ss15j crew pre aw13banana republic pre aw14selected homme aw14MASSIMO DUTTI NYC 5th avenue aw14river island christmas 2013

Dan May, Style Director At Mr Porter

“Manscaping is something I have never understood. There is no need for men to groom every inch of themselves. The designer stubble trend is there to look natural, so don’t try and sculpt your facial hair with too much precision. A perfect line under the chin is not what we are aiming for here.

“The same goes for plucked eyebrows and skinny sideburns. Adopt a more rugged approach and maintain, instead of changing dramatically.”

Fix It

Preening excessively is for footballers and wannabe R&B artists. Instead of extreme primping, take a more relaxed approach to grooming instead, which will give you a naturally kempt, rather than Photoshopped, appearance.

Naturally Groomed BeardImage: Todd Snyder White Label SS15

Final Word

Fashion is about making mistakes. From these mistakes, we decipher what works for us until – hopefully – the missteps become less frequent.

Which have you made, or see too regularly? Is fashion too beholden to its rules? And where is the line between experimentation and major error?

Let us know in the comments section.