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She Said Yes. What to wear on the First Date.

August 9, 2015

dateMy first date with my wife gave us some great memories, but none related to my fashion. I recently asked her about my attire at that lunch. She remembered that I wore my standard old pleated khakis and dark blue dress shirt. Not a terrible look by itself if the pants were newer than four years old and my shoes were not so scuffed. Since that day, I have had time to rethink how I would dress if I had that moment to relive.

Congrats, she said yes to a date with you. These kinds of encounters can generate plenty of nervousness; so, let’s dress you the right way to keep you from worrying about your fashion as well. First of all, make sure to let her know where you are going so that she can dress accordingly. The last thing you want is for her to feel uncomfortable about her own attire. A first date can take on many forms: nice restaurant and a movie, coffee at Starbucks, or a party. For the standard date scenario at a restaurant, try wearing dark straight leg jeans with a wild, fun and/or bright dress shirt and a khaki sport coat. No tie. This works for dinner at a nice but less intimidating restaurant. The exotic shirt says you enjoy life and the khaki sport coat tells her you have some sophistication.

I think we would agree that too formal a restaurant will scare her away – too much too soon. But, you never know when this scenario will present itself. Perhaps, your company decided to host a formal Christmas dinner and you need a date – a great excuse for asking a woman out. Or maybe, a bunch of your coupled-up friends press you to join them at the symphony and you don’t want to be the odd man out. If you do find yourself going to the symphony, wear a dark suit with a pocket square and a blue contrast-collar dress shirt with maybe a pink tie (Or you can reverse that: pink contrast-collar shirt and a dark tie).

Going to a ball game? Combine dark jeans with a grey v-neck sweater pulled over a white dress shirt and a good pair of leather loafers. It says cozy, yet refined. For the very casual date (maybe not even a date, but you are together) such as a game-filled picnic in the park with friends or the both of you helping a mutual friend move, try a good pair of jeans with a solid black crew-neck t-shirt and sneakers (give Converse Chuck Taylor’s a try in any color).

Assuming the date goes well; remember to ask her out for a second date. Have fun and make her laugh!

© Copyright Fashion for the average man 2015.

7 Comments leave one →
  1. Brian permalink
    August 9, 2015 10:13 am

    First date dress code in the UK is dictated by weather! There are plenty casual yet excellent restaurants to take any first date to so that is never a problem. I live in the centre of the city (although she rarely does!) so its usually walkable for me. In summer and if it is a lunch date, I would wear jeans or chinos with a formal shirt (ie collared) with the sleeves rolled up, depending on the temperature, Winter usually involves layers of course. I would wear a casual, unstructured jacket over a formal shirt…and in deepest winter a coat over that too! First dates need simple looks so she knows that you are a regular guy with no pretensions. Am suited at work but that is unimportant on a date. I don’t mind wearing a suit and tie – indeed I have many cool ties, but it looks a bit forced unless your date is straight from work. Then all I gotta work on is the 2nd date!

  2. Brian permalink
    August 9, 2015 10:14 am

    Feel free to comment or advise guys

  3. August 9, 2015 10:56 pm

    Sometimes one can never go wrong wearing a coat. Especially on a nice comfortable night out in the summer. Wearing a navy blazer could go a long way. No tie, unless the date permits. Wearing a blazer like such and a nice polo or button up would look quite sharp. I would most likely wear a polo that would pop under the navy.

  4. August 9, 2015 11:00 pm

    Wearing the polo would allow one to show off a stylish watch, matching with their belt and shoes of course. Wear a nice pair of brown pants for the classic combination with the navy blazer. Top it off with some attention grabbing cologne and the date should go wonderfully on your behalf. (Looks wise) It is always a shame when the male out dresses the lady. I get very disappointed when a lady fails to dress well for the occasion!

  5. December 13, 2015 8:35 am

    Cute post!


  6. February 27, 2016 9:54 am

    Haha great post!! xx

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