“God, you look like a …”

Insert the appropriate style paradigm here. Sailor, English huntsman, City banker, Italian lothario, geography teacher, preppy Ivy Leaguer. This is the reaction you normally get when an outfit has particular connotations for those around you.

But it is important to realise that everyone’s connotations are different. You can’t let your dress be driven by the subjective and very local associations of your peers. Instead, recognise the intrinsic qualities that have given these style paradigms longevity.

Let’s have some examples. If I wear a blue blazer with white trousers or chinos, I might be ridiculed in the UK for looking like a sailor. But in the US it is a staple of everyday dress, one step down from a suit and perfectly acceptable for business meetings.

It is also rather elegant – a smart, crisp combination that gives a lot of potential for great tan shoes, even spectators. Although it’s not to my personal taste, I would like to think I wouldn’t be put off by local connotations if I chose to wear it.

If I wear brightly-coloured driving shoes without socks, under narrow, short white trousers, someone might mock me for pretending I lived on the Italian Riviera. But in Genoa there would be no such remarks – everyone would be wearing it, at least in the summer.

It is also a rather chic option for casual wear. Both colourful and practical, it is a great way to remain stylish in the heat. On bright day in July, therefore, I wouldn’t worry about any associations of wearing it in Hyde Park.

Two quick caveats here. First, make sure you consider the practical background to a particular paradigm. Don’t wear white trousers and driving shoes on a wet, grey day; don’t wear a huntsman’s tweeds in the height of summer. An Italian wouldn’t do the former and an Englishman the latter. Second, make sure no paradigm ever slips into costume, as warned against in my posting here.

Red socks have connotations for some of arrogant City bankers, as do pinstriped suits, waistcoats, elegant umbrellas, braces, contrast collars and bowler hats. Don’t let that put you off – with the exception of the bowler hat I would recommend all of them, in moderation.

Brightly coloured trousers, checked suits, knitted ties, waxed jackets and tweed all have connotations of in-bred, grouse-stalking country folk. But that doesn’t mean they aren’t stylish, on their own or in occasional combination.

With each, consider what has made it a style paradigm. Think about why it is still worn and revered decades after it was first worn. Then take what you like and ignore your peers.