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Men and fashion, it is sometimes said, go together like socks and sandals. We rub along, but not comfortably or happily or prettily. It's certainly true that some men feel excluded from and threatened by fashion. The word alone is enough to make them break out in an unsightly rash. But this needn't be the case. Indeed, it shouldn't be.

Style, in my experience, is a less loaded term. It's harder, though, to put your finger on what exactly style is. It can be taught, but it can't be bought. Happily, there are rules. Rules that can be broken, but only once they've been understood.

That's not to say I always get it right, even though, as editor of Esquire magazine, I've been studying the rules for years. These days I wear a business suit to work. That wasn't always the case. I spent years as a scruffy hack in jeans and jumpers. But as I inched my way up the moisturised pole of men's style journalism, it became apparent that suits and shirts and ties and proper shoes were going to be more appropriate and less bother. I wear suits even on days when I could just as well turn up in shorts and a T-shirt. The challenge for me is the reverse of what it used to be. I'm sorted in the week. Now I struggle over what to wear at the weekends.

I'm not a trendy. Haven't been for 20 years. There are plenty of men who are – the peacocks, the dandies, the proto-Bowies – who have their own distinctive and individual ideas about what looks good. But how about everyone else? Men who want to look good, hip even, but not silly. Who want to be admired from afar but not pointed at in the street. Who want to be stylish but don't know how to do it. Who want to know: are skinny jeans still hip? Should men's ankles be on show again this summer? How late is too late for a slogan T-shirt? (Briefly: no; if you really must; any time after 1985 is too late for a slogan T-shirt.) Here are the rules for those men.

Should I grow a beard?

It's OK to grow a beard if you're Jeremy Paxman or a Shoreditch barista

Are you a barista in an east London coffee shop? Do you play in a folk band? Ride a fixed-wheel bicycle? Curate a Tumblr feed devoted to naked girls in 1970s Scandinavian cars? Are you Jeremy Paxman? Answer yes to more than one of these and you have my permission – even encouragement – to bin your Gillette. Otherwise, for goodness sake man, have a shave.

Should I get a size M or size L?

There is nothing less stylish than a man terrorised by his own trousers, nothing less attractive than a gut spilling over a too-tight waistband. Fit and comfort are crucial. That's why skinny jeans and deep-V T-shirts look ridiculous on anyone over 24 and 10 stone. But comfort comes not only from the right size but the right fabric. Basic guideline: in spring and summer, nearly everything you wear should be primarily cotton; in autumn and winter, it should be primarily wool. But even cashmere will feel uncomfortable if it's two sizes too small.

How much should I spend on a suit?

An inconvenient truth: you get what you pay for. By no means is high-end always better than high street, especially if you're under 30, but aesthetic and ethical considerations often go hand in (bespoke) glove, and for important purchases such as suit, shoes, winter coat – investments, you might call them – it's worth splashing out (N122000 minimum for a suit, around the same for a coat). As a rule of (lambskin-clad) thumb, if it's handmade in England, France or Italy, chances are the people who made it were paid and treated better than if it was mass-produced in the developing world. It'll look better for longer, too.

Which sunglasses will make me look cool?

Sunglasses that suit your face. There's no one-size-fits-all in men's style. If you look as if you're trying to be cool, you're not. And just because they suited Steve McQueen (the dead one) or Bob Dylan or Marcello Mastroianni, doesn't mean they're going to suit you. So try before you buy.

Can I wear colour?

The stylish man's colour palette, at least when it comes to major purchases, tends to be limited. Blue, grey and sometimes brown are correct. Lilac, lemon, mint, fuchsia, tangerine, not so much. Navy is the safest colour of all. I have navy suits, navy blazers, a navy overcoat, a navy waxed jacket for colder weekends, a navy blouson for warmer weekends. Formalwear is black or white, midnight blue at a push. Shirts are white, pale blue, perhaps pale pink. Leather shoes are black or brown. Injections of colour into smart outfits tend to come from accessories: red socks, yellow tie, patterned scarf. Red jacket, yellow shirt, patterned trousers? Not so good. At weekends or on holiday, of course, all bets are off – knitwear, polo shirts, swimming trunks can be any colour of the rainbow. I still tend to stick to navy.

What about patterned shirts?

Pattern is essential – the world would be a boring place without it – but it demands expertise. Generally, the rule is not to clash. If you are wearing a check jacket, make sure your shirt is a block colour, and vice versa. Leave the competing checks, the deliberately clashing colours and the oppositional prints (striped shirt with spotted tie) to the professionals. Better to mix pattern with texture. If you are wearing a patterned shirt, match it with a plain knitted silk tie.

How do I dress for the office?

A really good suit makes you stand up straighter, walk taller. Rightly or wrongly, it makes the world take you more seriously. And if it is cut right and fits properly (snug but not tight), and the cloth is soft and light, it is the most flattering thing a man can possibly wear. You don't have to go full bespoke to get a good one. Plenty of excellent off‑the-peg suits are available, and you can – and should – take them to an independent tailor after purchase so they can be fitted to you. As far as trends go, double‑breasted is fashionable again, after decades of obsolescence, and a very slightly more relaxed cut – a softer shoulder, a fractionally longer jacket, trousers fitted but not cut quite so close – has arrived to liberate us all from the excessively buttoned-up, Mad Men-inspired 60s-style suits of the past decade.

Must I wear a tie?

Don't follow our leaders in wearing a suit but no tie.

Business shirts need not draw attention to themselves. That's what ties are for: shocks of colour and personality in otherwise conservative outfits. Just know this: if you take your fashion tips from Cameron, Clegg, Miliband et al (in case you hadn't noticed, style-wise our political leaders are a bunch of middle-management dorks), you will find yourself going about in a suit and shirt with no tie, and you, too, will be unkissably uncool.

What does 'smart casual' actually mean?

Nobody really knows. It was invented by a corporate torturer to make men feel apprehensive when packing for office away-days. In these situations, it is always better to be over- rather than under-dressed. I take smart casual to mean soft, lightweight blazer (in navy!), business shirt, chinos (also navy!), loafers or brogues: all readily available from your local department store or mall, or, indeed, online from the comfort of your wingback armchair. Equally, you could wear a cotton bomber jacket over a lightweight sweater and polo shirt, or a weekend jacket in tweed or corduroy. Unless there's golf involved – please, dear God, no golf – I'd leave the cardigan at home. Too Tarbuck even for the 19th hole.

Denim might appear the most humble and democratic of fabrics, but jeans are fiendishly difficult to get right, as Simon Cowell so helpfully (and regularly) demonstrates. Many of us spend years trying to find the perfect pair of jeans – at which point that style is invariably discontinued by the manufacturer. I generally refrain from recommending specific designers or items, but fashion is full of exceptions and here's one: APC, a rather esoteric French brand, makes a product named New Standard Regular-Fit Selvedge Denim Jeans. I have numerous pairs, in various stages of disintegration. They obey every rule of good jeans: medium-rise waist; straight leg; slim-ish but not skinny; raw, indigo denim (it'll fade); absolutely no branding, or unnecessary stitching, or rips, or diamanté. By the way, that whole thing of wearing your jeans with a suit jacket, canvas trainers and an open-necked shirt? It doesn't make you look like a Lower East Side art rocker. It makes you look like an oily Euro sex pest.

Should I wear trainers to work?

This brings us to the question of kit. Kit is anything with a practical application beyond keeping you warm – or at least covered – and presentable. Walking boots, motorcycle jacket, tracksuit, these are all examples of kit. They should all be worn for the purposes for which they were designed. So: walking, riding a motorcycle, playing Nintendo Wii while eating crisps. Some very uncharitable style snobs include trainers – or sneakers, as fashion people, irritatingly, have taken to calling them – under the "kit" banner, insisting tennis shoes should be worn only to play that sport, running shoes for running, and so on. I'm of a younger vintage; I grew up fetishising sports shoes and am secretly thrilled that after years when technical trainers played runner-up to scruffy Converse plimsolls, colourful, mass-produced blobjects are back on fashionable feet. Word to the wise: unless you are a twentysomething creative at a bleeding-edge east London start-up, save your trainer-wearing for the weekend.

How much attention should I pay to accessories?

If you can afford it, a good Swiss-made watch is a handsome thing to own – watches being, for most men, the only way to ornament themselves these days, eyebrow rings being so passé. A decent diver's watch goes up from high price to infinity. (Start saving now.) As for handmade English leather shoes, the really well-heeled man will own at least one pair of the following for work: leather oxfords, leather brogues, leather loafers. I would add to that: weekend brogues, desert boots or chukkas, suede loafers. Admittedly, none of these is cheap. But they are built to last. My Tricker's brogues were bought in the late 1990s (in the January sales, for less than £200) and I wear them at least once a week. I have them resoled occasionally, polish them regularly and see no reason they won't outlive me. My Panerai watch, also acquired before the turn of the century, has been worn every day since, except for two brief periods when I've sent it to be serviced. Equally, you could wear Crocs and a plastic digital watch.

What should I wear in bed?

I have reached a certain age. I wear pyjamas (Derek Rose, if anyone's really interested). But there are no rules in the bedroom, or at least none I want to lay down. Wear a silk dressing gown over a terrycloth pantsuit if that's what'll get you through the night. Wear a vintage West Brom football strip, wear a leather catsuit, wear nothing at all, let it all hang out, see if I care. Sometimes, a man should do and wear whatever the hell he pleases, and the rest of the world can go hang. Fashion's about that, too.

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