A jacket like this but, you know, well made

Suits don’t necessarily fit into everyone’s day-to-day life. For some, in an office full of corporate lawyers, a suit is a necessity and a uniform. It is almost harder to take an interest in clothing that is imposed on you in this way. For other men, the barrier to developing a sartorial interest is the lack of suits in the office. Dressing up when everyone else is dressed down will draw attention; not everyone wants that kind of attention. Trying to show off? Who do you think you are? You’re not impressing anyone you know.

My advice is, dressing well is a question of degrees. So take what your peers wear and up it a notch.
My brother works in advertising. The dress is extremely relaxed. When the Ashes are on TV, and music plays continuously when there isn’t a suitable sporting event, the attitude to attire is unlikely to be strict. I’m not sure it’s encouraged to wear shorts in the summer, but it isn’t forbidden. Mad Men it ain’t.

A suit, shirt and tie would certainly be out of place. But there remain many sartorial possibilities. The key items to dressing well (and, let’s face it, the routes to the most pleasure) are jackets and shoes. So let’s put our hypothetical advertising executive in a light grey, herringbone jacket and brown cap-toe Oxfords. He can wear a bespoke shirt if he wants – precisely ironed, windsor collar – or an old, beaten-up favourite from Brooks Brothers. It doesn’t matter really: as long as he wears the jacket most of the time, its sculpted, flattering lines will make him look good without showing off. He can also wear jeans, preferably in a straight or narrow cut, in order not to distract from the tailoring above the waist, but otherwise of a make and price tag of his choosing. The legs will be perfectly finished off by the cap-toes, which will be benchmade in England, perhaps even bespoke, and so suggest sophistication with the turn of their waist and angled heel. All without shouting.

Bespoke is best, but the bald fact is that any thought put into clothing today will stand out. If not bespoke, then made to measure. If not MTM, then at least a ready made suit with a handful of adjustments. To sculpt the waist and bring the sleeves up to the correct length. As to the shoes, start with something well-made and move up one step at a time. If you’re in the US, begin with a nice pair of cordovan Aldens. Then perhaps something English, an Edward Green. Finally, turn to the masters of bespoke when tastes and wallet have expanded to that point.

The point is, this man would appear casual, relaxed in any office short of an Australian surfing-tour company. You don’t need to wear a suit and tie to be well put-together. You just need an attachment to the classics of style and, most of all, to fit.

Oh, and one last suggestion: rather than wear something that shows off, like a flowery pocket handkerchief, add a cardigan underneath the jacket in a dark colour like navy. It flatters in just the same way as a waistcoat, but doesn’t look cheap (all waistcoats do unless they are tailored – it’s just impossible to make something fitting that close to the skin in a standard model).