What To Wear On A First Date

Many grown men do not know what to wear on a first date.  Plus, first dates can be tricky.  Many daters do not want to agree to have a lengthy dinner with someone they do not know well in fear that they will be held hostage at the restaurant until the bill shows up.  Coffee dates and getting drinks after work are increasingly popular ways to meet someone new without making a big commitment.  Whether you are going to the coffee shop or meeting for a weekend lunch, there are a few things men should wear on first dates, and there are a few items that men should never wear on first dates.  On a first date, you want to dress like you care.  This means:

  • No workout clothes
  • No ripped or stained clothing
  • No flip flops
  • No board shirts

Dress for the venue, but also realize that you can find men’s luxury apparel that does not look ostentatious to the neighborhood park.

What to wear on after work dates

Learn to love the concept of dressing up work clothes and dressing them down.  One of the easiest ways to look ready for a night out instead of a long day at the office is to invest in a classy sports coat.  A full wardrobe change between the office and the place you are going to meet immediately after work is not always realistic.  Instead, make your khakis and dress shirt look classier with the right sports jacket.  The right sports jacket can take your everyday work attire from boring work clothes to eye-catching first date attire.

All about shirts for men and first dates

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Depending on where the date is, you can have a few different options for shirts.  An evening date will often call for mens dress shirts, but you can wear a nice t-shirt on a weekend coffee date.  Polo shirts and sweaters are also good first date ideas.  When in doubt, think about wearing a shirt that shows you care about the date.  Hooded sweatshirts are generally a poor idea as are sleeveless shirts.

Shoes, shoes, and more shoes

Some men like to think that wearing the right shoes only applies to women.  Again, you want your entire dating ensemble to show that you care about the date and the woman you are going out with.  Workout shoes, work boots, hiking boots, sandals, and beat-up tennis shoes are all not good first date shoe ideas.  Find a few pairs of casual shoes that you like.  Make sure that your shoes go with your overall outfit.

The Takeaway

Know that you wore an outfit that was respectful and showed that you were excited about the date and meeting your potential match.  You can find someone that loves you for you, crazy wardrobe and all.  In order for her to see your great personality, you need to wear the right clothes first.

  • Do not wear anything that could be seen as goofy
  • When in doubt, overdress instead of underdress
  • Always dress to impress

Remember, you never know when the blind date you are set to meet at a local coffee shop might be your future wife.

Benny White is a writer and blogger and likes to report on subjects where life meets business.