Wining and Dining with Style


There’s nothing quite like dining out. Though the unenviable tasks of meal preparation, wine pouring and washing up have been passed on to capable, professional hands, venturing out for a bite to eat poses a problem not necessarily associated with the comfort of home feasting: what to wear.

When I have been fortunate enough to dine at restaurants of exquisite taste and marvellous cuisine I am often shocked to see a couple of roguish customers, crouching over their glasses of Margaux in skin-tight t-shirts from the likes of DSquared or Dolce & Gabbana. These martyrs of the dining world, who are very likely to believe that the more they spend on a t-shirt, the more acceptable it is, are in fact the laughing stock of the entire restaurant. And, what’s worse, they are so conceited in the appeal of their self-indulgent materialism that they actually deign to attend conspicuously formal restaurants in this most crude and inappropriate clothing.

One does not have to swan around in Savile Row suits to be acceptable for such places and nor do you have to spend, contrary to common ‘wisdom’, vast amounts of greenbacks on designer goods and accessories. Dressing appropriately and elegantly can be relatively inexpensive and sets you apart as a citizen capable of respect: respect for the surroundings and for the other diners.

In order to dress appropriately, and not merely exceptionally, it is important to consider certain factors. Firstly, where will you be dining and secondly, what is the occasion. Some chaps might take very little time to consider these options; a brief enquiry as to the destination, a ‘wear-something-nice’ return comment and hey presto – this particular chap is ready.

I believe that, for other men, it is rather more complex. A Michelin starred Roux establishment calls for a different sartorial approach than a funky and crowded sushi destination. This is not an argument for ‘blending in’: I would never encourage a gentleman to disappear into the fabric of the place. A man of style should be discreetly noticeable, but he should also be capable of chameleonic modification.
Having a personal style is important, but adapting to surroundings should also be of interest.

How much to add, or indeed take away from your personal style is a question of taste and occasion. Those with a very relaxed and minimalist style may wish to ‘add’ significantly on special occasions. Likewise, those with a rather foppish dress sense may find they will benefit from ‘tailoring down’ on their way to a simple trattoria. I do not encourage such harmony from any desire for picture-postcard symmetry but for the personal comfort and enjoyment of the gentleman in particular; adjusting your threads in reverence to the surroundings can help you to relax and feel comfortable.

In the richly wooded and velvet-trimmed surroundings of a very traditional restaurant, it would be appropriate to dress complementarily; a nut brown suit, light blue shirt, chestnut Oxfords and perhaps a silk or cashmere navy blue heraldic tie would be perfect but if this sort of attire does not appeal, ‘going neutral’ is acceptable; a dark blue or grey suit with a crisp white shirt and chocolate brown shoes. The advantage of the ‘neutral’ look is that it can, in the parlance of modish fashion writers, ‘take you anywhere’; from pre-dinner drinks at a contemporary bar to post-dinner clubbing in low-lit Soho dens, the ‘neutral’ has an advantage when it comes to flexibility.

When it comes to a casual meal with friends; no build up, late notice, inexpensive, contemporary and informal, your ‘neutral’ uniform will still be effective but in some circumstances it might look a little contrived; making-an-effort-to-not-make-an-effort can be rather obvious at times, so removing the trousers and replacing them with smart denim, or conversely, removing the jacket and replacing it with a cardigan or a good v-neck jumper is a good idea for establishments that have a noisier and more youthful edge.

A female friend once told me that dressing empirically well is impressive but that dressing appropriately is even more so. Living this advice can be challenging but it’s an awful lot of fun. Need something for a smart seafood restaurant in Maine? Perhaps a double-breasted navy blazer with contrasting white buttons, light blue slim chinos and a high collar white shirt. Or something for a stylish, contemporary tapas joint in Barcelona? Maybe some white denim, some white loafers, a cream shirt and a sky blue two-button linen jacket. There is certainly pleasure in choice and there is an even greater pleasure in looking the part.


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at