Tinder-Pro And Living Dandy Winston Chesterfield's Guide To Creating The Perfect Dating Profile

12 February 2014

Tinder is a minefield. It’s also terrifyingly successful and popular, racking up 600m swipes every day. 600m!

None of this explains the varying sartorial and pictoral quality of some of its users – bearing in mind this is a looks-only app, you know, like Hot or Not, some of the looks beggar belief. So, we asked Tinder-pro and living dandy (aka research consultant for luxury and prestige brands) Winston Chesterfield, below, to talk us through what worked and indeed works for him.

My normal style is fairly formal. I wear suits everyday, and love accessorising with pocket squares and tie-clips.  

However, my view on attraction is that it is all about balance. Presenting only my ‘working best’ side isn’t exactly truly representative - I don’t wear three-piece suits on a boat in Greece - nor is it very appealing to women. Stiffness in attire is not attractive, it seems.  

I have been on Tinder a couple of months. I chose a selection of photographs that provided a balanced picture of my lifestyle, providing the ladies with a suite of situations in which she can visualize being with you. It also serves to add interest and depth to your character; a man of evening functions, of important business, of travel and one who enjoys his leisure. In other words: a knight in non-shiny wool.      


Different variations of black tie were very popular with the ladies. These formal pictures attracted commentary of admiration and intrigue, with women approaching the conversation from the point of view that I was something of an international cad who wore evening dress regularly. It was clearly very important that I was seen to be comfortable wearing it, having fun and not trussed up in a black wool strait jacket. Holding a drink and chewing a cigar may make me seem like a bit of a playboy, but it sparked something in the matches.        



Also highly appealing were pictures of me in suits (particularly three-piece) wearing ties, tie-clips and pocket squares. This kind of formality prompted the ladies to ask about my job, wondering exactly what kind of profession required such sartorial maturity. Some of them even mentioned that it was hard to find men who liked dressing properly and a notable number of these matches were very well-dressed women who had similar interests in art, music and fashion.  


The casual outfits that worked best had either a continental coolness to them, or were distinctly British with a contemporary edge. Simplicity seems to be equivalent to sexiness in this context, although getting too casual didn’t work. This ‘weekend’ look worked best with the non-English ladies who saw the corduroy jacket, open shirt and V-neck as quintessentially ‘Brit boy’ – surprisingly less appealing to girls from the UK, who seemed to prefer a swarthy, international look.


Relaxed holiday pictures really help to balance out the formality of the rest of the collection. Some girls were relieved to see that I didn’t wear a jacket and pocket square all-day everyday - particularly in searing heat - and that I could kick back in a linen shirt, sunglasses and espadrilles. Though sunglasses were unpopular when used in isolation, if they can see your eyes in the other pictures, it didn’t seem to matter. Crucial to this picture is not to pout; it’s OK to look moody in other pictures, but if you can’t have a good time on holiday, where can you? 

Note to the reader: should any of these take your fancy, Winston is on Tinder


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