"What to Wear on a First Date"

03rd January, 2013

There are few rules on how to dress for a first date.


Few rules that are equal and should be respected in any case, no matter if you are straight or gay.


Indeed, these are the key guidelines that should be followed when you want to maintain a high masculine and manly profile with your date.


Keep always in mind that the preparation for a first date always depends on WHO you are meeting. So some due diligence on your “hot date” before the meeting is always good to be performed.


Two fundamental things are always worth to be known in advance:


1. whether she or he is vegetarian (so that you may avoid to inviting her or him to a brasserie for dinner);

2. in which industry he or she works (so that you know also exactly what to wear in that first occasion and whether to go very expensive or relatively economic safe...)


To make it easier, we have divided the RULES into three main sections: the Clothing, the Accessories and the Grooming.






But not too much...


Meaning: please opt for a clean and simple look. Try not to look uptight or somehow constrained, but relaxed and comfortable in everything you wear.


Avoid everything sweaty and too warm: it is a first date... There will be many occasions to get excited and it is better to avoid easy heating.






Generally, try to wear clothes that fit you.


Don’t forget: the ultimate goal of this exercise is to see each other naked.


So fitted clothes might give her (or him) a reasonable approximation of your dimensions underneath.



An impression, like a good outfit, is difficult to make, but when your behaviour is in concert with your wardrobe, well, good things happen.


The first thing you need to realize is that the presentation of yourself shows your level of respect for her (or for him).

So dress properly for the date. Don't sweat the tie (unless your destination requires one), otherwise you will feel too dressy. Still, a jacket would be an excellent idea.


If you go to a fancy restaurant or cocktail bar, opt for some dark blue denim (without holes here and there) or other dark trousers.


Ideally, a look that is ALWAYS right is the following: white shirt, black or dark grey jacket, blue indigo denim. Eventually, you can swap the shirt with a black round-neck collar T-shirt.


Your goal on date night is to be at leisure, or at least maintain the illusion of it. And separates, or a nice sweater, will convey just that.


Also, don't wear a suit. This might seem counterintuitive, but easy to understand why: if you are going to the opera, fine. The theatre, maybe. Otherwise, you will seem uptight.


Sure, the nicest things you own are probably tailored suits, but those suits are better for proper working office hours — so, please, leave them in the dry-cleaning bag until Monday.




Don't wear anything to which the words "zany" or "interesting" might apply.


T-shirts with sayings on them (not even "Sexy Beast" or "I am a Lesbian"), your "Mr. Burns for Mayor" pin, dad's old hunting cap — they're not going to show her how clever you are. So don’t wear ANYTHING with a LOGO.


Sporting attire should be avoided at all costs, unless your date involves watching or participating in sport events. In which case, there probably won’t be a second date. So no GYM suits, please.





Because you never know how the night could end... J





Pick an appropriate pair of shoes— lace-ups or loafers for the evening; driving shoes, moccasins, or simple sneakers for the afternoon; flip-flops for nothing, ever — and you’ve scored points before the handshake.


Shoes are so important to get the right impression...


Don’t underestimate their importance with any female (or male) date: they will tell everything about you and especially the level of care of yourself too...


Good-quality leather lace-ups or loafers are the safest bets.


Socks are scarcely less important and should be fine wool or cashmere.


Seriously, we really can't emphasise this enough.

There is a say out there as such: never trust a man with unpolished shoes.

But also: don’t trust a man whose shoes are TOO polished.


And we add another one: don’t trust a man with flip-flops (or mandals), especially if combined with a suit (and trust us... we heard this happening different times, with regards to opposite and same sex dates!!)




Because all the points you earn by paying for dinner will evaporate in an instant if your billfold says "Bad Motherfucker" on it.


Put your money into brown or black leather.


A clip can be a stylish alternative as long as it isn't in the shape of a dollar sign.




1. Clip your fingernails. Wash your hair.


Women (and gay men) check the details.


They look at a man's hands more often than a man looks at his own.


Make sure yours are presentable. So clean and trimmed fingernails are very important.


Also, they will see those little flakes on your shoulder, too, so don't be too shy to break out the dandruff shampoo.


If this is a problem for you, avoid wearing a dark shirt.




But not too much.


If you smell like a tart's boudoir, than she may suspect that you frequent one.


If in doubt, go classic and unassailably masculine: Terre d’Hermes, Aqua di Parma, pretty much anything by Tom Ford or Armani.


Spray on your chest under your shirt and on your hair to give her an incentive to get closer - wrists and neck wear off too quickly - and never down your trousers.


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