Itching to wear a hat? Wait another 50 years

STYLE CLINIC:I am a 20-something man and consider myself relatively stylish, and I'm thinking about starting to wear hats. I'm not sure what kind – maybe a 1920s style.

But I’m a bit worried it’ll look pretentious, when really I want to look like someone from the 1920s. I tend to wear slacks with shirts and waistcoats, so wouldn’t this be a natural progression?

Jasper, by email

Jasper (if ever there was a name designed for a man who wanted to wear hats, it is yours), wearing a hat as a casual fashion statement is a little pretentious, and there is not much that will change this, bar age. When you are in your 70s, Jasper, you may do as you wish and wear hats all week long.

Your combination of slacks, shirts and waistcoats with a hat bothers me a little; when worn with a certain insouciance and items from Topman, hats can look cool and ironic.

When worn with slacks, waistcoats and shirts, you may appear as if you take yourself horribly seriously or have just stepped off the stage at the Abbey.

Despite those significant misgivings, I am firmly of the opinion that fashion should be enjoyed.

And so, Jasper, if you want to wear a hat, well, do. Just don’t come crying to me when all of the other boys laugh at you behind your back.

Winter coats – the long and the short of it

Without wishing to inspire more talk of rules in fashion, I would like to know what is acceptable in the world of coat lengths. I tend to wear skirts and dresses that rest on or just above my knee. I would like a dark coloured winter coat but find knee-length coats to be a little mumsy. I’m tall and in need of something classic and stylish (colour not a concern) that can be worn with skirts and dresses. Don’t suggest a cape.

Louise, by email

This season has really brought home the idea that there are no rules in fashion, at least when coat lengths are concerned. Victoria Beckham’s A/W collection inspired myriad high-street copies: military coats that stopped mid-calf, and flattered no one except, one can imagine, La Beckham herself. So we shan’t be talking about rules on this day.

What you’re looking for is a coat that hits mid-thigh, or slightly above your hemline. Any lower and you run the risk of looking like a woman who is wearing nothing beneath her coat; any higher and you’ll break up your “line” too much, like a Lego character with separate top, bottom and head segments.

This coat by Asos.com(€138.90) is a great colour and shape. It's classic without being boring, and the length is perfect for what you're after. It also comes in a khaki-beige shade.

Tommy Hilfiger’s Hudson coat, at €335, may not be the most bargaintastic coat out there, but it is a really beautiful, classic piece that will take you from winter to spring and beyond. It’s cotton moleskin, which means it’s super soft and cosy, and it comes in navy and in a gorgeous green shade called darkest spruce, which is a great alternative to black or navy (but not as out-there as, say, emerald green). Cutting just below the thigh, it’s also a great length – it looks like a classic gentleman’s coat with a modern twist, and is really flattering. Wear with a chunky scarf, or over a buttoned-up collared shirt.

Another wool-blend option is this double-breasted overcoat from Zara (€129), which is a great shape and colour (navy). It’s got a slight flare below the hips, which is super flattering, and the wide neckline will add shape and draw attention to your décolletage.