Your most pressing style questions answered
What do I wear when the dress code is smart casual?
Pretty much anything smarter than a tracksuit, but less formal than a suit. An ideal answer is a blazer, white shirt, neat jeans, and brown loafers. The key is not to worry about being over dressed; few people who matter will worry that you looked too good.
At what age does it become embarrassing to wear jeans? I don't want to look as though I'm trying too hard.
It's not about age; it's about attitude and abdomen. Jeans, like all flat-front trousers, are unforgiving and uncomfortable if you're not relatively slim. If you're in shape and you pick the right pair there's no reason not to wear them until you pop off.
My weekends are spent in the park with the kids. What can I wear that will look good, but go into the washing machine at the end of the day?
Start with solid brown-leather brogues or boots with moulded rubber soles, then add jeans or narrow-cut moleskin trousers, a cotton shirt, a wool sweater and a waxed-cotton jacket (with a quilted lining). What's intentionally missing from this list is sportswear in manmade fabrics; set your children an example by holding out against fleeces and tracksuit tops.
I divide my time between country and town. Please suggest clothes that will be appropriate in both.
There isn't much that works as well in Hoxton as it does in Herefordshire, but the key is to find clothes you like that are irreproachable in both environments. Let the city decide the cut, rather than buying baggy country clothes, but choose colours and fabrics that work in the country - think tweeds, moleskins and cottons in gold, brown, red, green, and blue.
Can I wear a T-shirt under a jacket in the summer?
Of course, especially if your name is Sonny Crockett. Actually, it's a great bohemian look. London dandy and stylist William Gilchrist frequently wears a T-shirt under a soft double-breasted jacket and the effect is admirable.
My friends dress very casually and it would be odd to wear a jacket and tie when I see them, but I cannot bring myself to go out for dinner in a T-shirt and hooded sweater. Is there a halfway house?
Yes: slim chinos, desert boots, a colourful belt (either woven or in canvas), a button-down shirt, a fitted cotton jacket, and perhaps a knitted tie. It will be smart enough to set you apart, but casual enough for you not to feel odd.
I am newly single and I want to update my wardrobe. What should I be looking for and what should I avoid, with a female audience in mind?
Do not try to reinvent yourself, because it will probably be unconvincing. Instead concentrate on updating the classics for a fresh and contemporary look. Jeans, shoes, shirts and suits mustn't look outdated or worn out. Few girls notice the intricacies of how a man dresses, but they are likely to notice your watch and your shoes; either can be taken as an indication of your income bracket, so make sure you're happy to be judged on them. And it's obvious, but make sure you reload your underwear drawer.
Why do people wear really garish tweeds?
Because when men step out of the sartorial comfort zone (blue jeans, white shirt, navy blazer) they can easily mistake eye-catching for elegant; there's a big difference between being notably well dressed and merely notable. Compared to sober city colours, tweeds are already imposing, so there's little need to turn up the volume.
I can't work out what it is about Italian men that makes them look both stylish and relaxed. How can I steal a bit of their elegance?
First, let's remember that many Italian men want to dress like an idealised Englishman. Second, you're not alone - it was precisely this question that inspired The Sartorialist to start his blog. Extreme conservatism plays a major role: the men you admire have been dressing the same way for years or even decades, so you'll need a high boredom threshold. As a function of this, clothes are bought for the long haul, and are more likely to be better made to start with and then altered for the perfect fit. Beyond that it's about subtle colour combinations, which frequently involve brown, grey and navy, and immaculate presentation. As Charles Eames once said: 'The details are not the details. They make the design.'
Does it really matter what I wear? It is surely reasonable to expect the people I meet socially to judge me on my behaviour, and the people I meet professionally to judge me on my results, not my ability to buy the right shirt.
Mark Twain said: 'Clothes make the man. Naked people have little or no influence on society.' We can't improve on that.