Well congratulations! You have convinced someone that you are interesting, attractive and worth spending more time with. Breaking this down into simpler terms, you have a date! This is the exciting part, because you have made that first impression, and it turned out to work in your favor. But the hard part has yet to come fellas! You now have to convince this person that you are indeed a gentleman and worthy of a second date. Part of this presentation is in your outfit. This is key, because different venues requires different styles. Therefore, I shall provide simple, yet effective outfit ideas for different dates.

The Dinner Date:

  • This is a popular first date choice. Dinner dates are more personal; a chance to get to know one another face to face, and that means she will definitely notice what you are wearing.
  • This typically calls for the semi-formal attire. Not completely suited and booted, but close.
  • A great option would be a button down shirt, paired with trousers and a casual jacket. (I prefer the bomber jacket. But for the more fancy restaurant, opt for a casual blazer).
  • Alternatively, a pair of clean jeans or chinos, paired with a t-shirt and an optional blue blazer looks smart. The jeans or chino option provides the hint of casual that is definitely a necessity.
  • You have a few options for footwear, ranging from traditional dress shoes (i.e. Oxfords), to Chelsea boots for the classy alternative look, or desert boots for a more casual aspect to your outfit.
  • Hint: Go for the Chelsea boots; always a good conversation topic. Yes guys, they will focus on what shoes you wear.

The Activity Date:

  • This is my personal go-to for the first date. It’s fun and usually brightens up the mood and atmosphere, and typically leading to that second date approval.
  • Keep the blazer in the closet, chill out, and rock the street-wear style.
  • For example, try fitted blue jeans, a comfy jumper or a casual plaid shirt as an alternative top.
  • Dress shoes or Chelsea boots are perfect for activities that aren’t “sporty”.
  • Alternatively, you can finish the look with a clean pair of shoes, such as white or black Converse. Remember, this type of date requires some fun activities, so you want to look fresh, as well as comfortable.

Credit: @orein2727


  • This is a very relaxed setting, so your outfit should match the atmosphere.
  • Your style falls in between the dinner date and the activity date. This means you want to look smart, but at the same time be slightly more casual and comfortable.
  • For example, joggers paired with a jumper or a plaid casual button down shirt, and white converse shoes.
  • Alternatively, slim fit blue or black jeans, a fresh white t-shirt and a bomber for a more casual look. Pair this with black suede Chelsea boots to add some flare to your outfit.

Whatever the choice of date may be, your outfit says a lot about who you are. This is a great opportunity to present yourself as a gentleman who cares about his appearance. Essentially, this will give you brownie points. Just remember, you want to look fresh, which means your outfit is on point with no rips or stains, your shoes are as clean as possible, and your style matches the date setting. If you do these three things, you are setting yourself up for a great first date!

For more style tips and ideas, head over to my Instagram page @dysfunctionalwardrobe.



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