What Men Should NOT Wear On A First Date

  1. WearTight Tee Shirts
  2. Wear a Suit
  3. men on first date

A lot of men are not interested in clothes to the same degree that women might be, and so a few tips are in order as to what you shouldn’t wear on a first date. The fact is that women do take notice of what their date is wearing, and this is especially true for a first date. You are probably aware of that fact and know that if you want a second date, you should take care when it comes to choosing what you intend to wear.

WearTight Tee Shirts
When Not to Wear Tight Tee-Shirts

A tight tee shirt may not be appropriate for a first date, it depends on where you intend to meet. If you have met a girl who is keen on sports and you’re going to see a ball game, then a tee shirt will be fine. Dinner dates and drinks however, may require something a little more formal, such as a shirt and slacks, wear a jacket if the evening is cool.

Don’t Overdress

Wearing something new and different will not only put you further out of your comfort zone, it will be obvious to her. As it’s a first date she might assume that it’s her company that’s making you appear uncomfortable, rather than the unaccustomed clothing. A good rule of thumb for a first date is comfortable, smart casual.

Don’t Wear a SuitWear a Suit

Nowadays, men only tend to wear suits to the office or if they are attending a function where formal dress is required. Most modern women wouldn’t expect you to wear a suit. If you want to feel comfortable with your date, then dress comfortably but not too casually.

Casual is as Casual Does

Most first dates involve meeting at a wine bar or grabbing some supper before you go to the cinema. Keep things casual as you normally would on outings like this, but not so casual that your clothes are more suited to a football match than a first date. Casual does not mean sloppy, make sure that you are clean and tidy.

Leave the Khakis at Home

You may feel comfortable in khakis but if you want your date to know that you are a cool guy, then perhaps casual slacks might win over khakis.

Not a Good Fit

A jacket that is too tight for you, a shirt collar that is obviously choking or pants that are a bit short, are out. Make sure that what you are wearing fits you well or she may decide she is dating a charity case.

Ditch the Polo

Unless you plan to take her for a game of golf (guaranteed to eliminate chances of a second date), don’t wear a polo shirt and formal trousers, they can be off putting. Wear a decent, (not skinny) pair of jeans and a shirt – if the weather is cool then wear a casual jacket. Keep it simple and enjoy yourself, that way you might be in with a chance for another date.

men on first date

Crispin had to learn it the harder way in fashion which is why he is very keen on helping men not make the mistakes he has made. He loves shopping from unique menswear retailers.


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