There is no such thing as over dressing for a date. There is such as thing as dressing too casually. The biggest mistakes grown men make on dates is heeding the advice of girls when they tell you ‘just be yourself’.
My advice for dressing for a date is don’t be yourself, because ‘yourself’ is single and gives you horrible advice.
You might think fashion isn’t important. Even one of the greatest trailblazers of the 60’s peacock fashion era, Mr Fish, was quoted as saying, ‘people get hung up on fashion, it’s really not that important’.
Don’t be duped. Your style and what you wear on a date could be the deal breaker. I remember on a lousy date back in the day (before I really took much notice of fashion), I took a girl on a date on a bitterly cold winters night in South Putney. When it came time at the end of the night she rebuffed my advances.
Somewhat crestfallen I asked why? She said bluntly, “Well I’ve turned up in this,” highlighting her gorgeous figure hugging black sequin dress, “and you’ve turned up in that,” pointing at my generic black gilet.
The enormous golf between us immediately evident, and it wasn’t just disparate worlds of style, it was that she had gone to the effort of looking nice. So where are mature men going wrong with style? Not putting in the effort.
Women have uncanny knack of knowing whether you’ve just come from the office, or you’re wearing the same outfit you’d wear to your friends BBQ. You need to first and foremost, make the effort.
Women notice these before anything else. Well, they notice a man’s height first, then it’s the shoes. Then it’s the ass, your face is somewhere in the mix but believe me, your shoes usurp most boxes to be ticked.
I was in the room once when a girl gave a friend of mine an excoriating review of a friend’s style. I asked the girl in jest, ‘You would date Tom wouldn’t you?’ She fired immediately, NEVER!
Poor Tom, “WHY,” he asked broken hearted.
“Tom you wear shoes that looked like they were bought in the 80’s and last cleaned in the 90’s.” The next day Tom text me a picture of a pair of wingtip brogues he had just purchased from John Lobb on Jermyn Street. Tough love is some medicine.
Where guys go wrong on dates is not so much the style of the trouser, but the fit and the colour. Women tend to hate corduroy. In fact I’ve never met a woman that likes corduroy on a man so keep those tucked away until you have your feet under the table.
If you’re going Chinos, don’t gamble on what Steve Coogan refers to as “Those twat colours.” Personally I don’t mind “twat colours.” I wouldn’t wear them per say, but people can be overly sniffy about these kind of things. New & Lingwood do a quite exotic collection of multi-coloured chinos and they look fantastic.
My point is, don’t gamble on dates. Don’t run the gauntlet of trying to looking young, hippy, happy-go-lucky. Mature women don’t want chancers, they want virile men. They look for resourceful men. That’s why the whole Crocodile Dundee film is flawed.
Sue would never ditch money bags Richard for some penniless chain-smoking Aussie who had zero utility in the city.
It’s the fit gentleman. That’s all I want to say on the matter. Where a shirt on a date to prove you made an effort. That this isn’t just a stop gap on the way to see your mates at the boozer.
A fitted shirt you can find quite readily at Hawkins & Shepherd. I have an unbelievable amount of shirts, all varying styles and fits for all occasions.
Failing that, get a shirt from a shirtmaker that will be absolutely nailed on to your body shape. You will pay a premium, but see it as an investment for your future. If you want express some individualism why not try Turnbull & Asser and have some fun with the cuffs. Their signature cocktail cuffs are the best.
Nothing grey! No woman I’ve ever encountered has told me she finds a grey suit jacket on a man attractive. You might have some misgivings about putting on a jacket for a date. Seems a bit stiff right?
Wrong. Dead wrong fools! You’re a grown up now. No denim jackets, no biker jackets, no bomber jackets. You have to prove to the lady in question, that after this date, you can go on to any members club in London. In fact you’re dressed so well, it becomes like a scene from Goodfellas where they welcome you with open arms like and give you a table at the front by the band.Please Note: I’ll be one of the men’s coaches at the Dating Show Live in June if anyone would like some one-to-one advice or support.