Enclothed - Delivering Your Style

What to Wear on Your First 3 Dates

What to wear on your first 3 dates! Generally, the first 3 dates a guy goes on will set the tone for a long-term relationship – or an early exit. Therefore what you wear during these 3 initial meetings could be more crucial than what you wear for the rest of the relationship.

We already gave you tips on how to get your foot in the door with good shoes.

Now that your foot is in said door, you need to turn things up a notch.




The first date is usually pretty chilled. Perhaps after-work drinks on a Thursday evening at a convenient location for both of you. If you’re a corporate guy that does the whole suit and tie shebang then your work is cut out for you. But you may still want to switch things up a little bit by carrying a different coloured button-less blazer in your bag when you leave for work in the morning. Besides, God forbid you spill any coffee on your work blazer during the day. Alternatively, you can carry a crewneck jumper (that doesn’t match your tie) and lose the suit blazer come 5pm. If nothing else, this will at least show her that you’ve been thinking about the date the whole day. Cool points for you.




You can get a little more adventurous style-wise on date number 2. This one would most likely be on a Saturday for brunch or lunch, perhaps somewhere outdoors-y or with good lighting. A denim jacket is always a good bet. You can pair that with either a striped t-shirt or a solid coloured polo shirt. Throw on some tapered trousers or chinos with white trainers to show her your casual but sophisticated side. Besides, you may want to take her on a nice stroll after.




Things are serious at this point. The third date would probably be a 3-course dinner and drinks somewhere on a Saturday night. You’ll need to bring out the big guns. The most important items for this look would be your shirt, watch and shoes. Everything else should fall into place when you have got it right with these 3. Get a solid white or black dress shirt with no pocket. No need to wear a tie so go for something with a small collar. The type of watch you wear depends on your personal preference but make sure it’s nothing too flashy that will distract her from the conversation. Cuff links are important – make sure they compliment your watch.  We prefer brown leather oxford shoes over black ones, only because it’s an intimate date and not a formal event.




You have won her over mate. Congratulations. You can now let your inner peacock out with all its glory. At this point you can pretty much wear whatever the hell you want. Show her a little of your wild and cheeky side. Surprise her with a few hats, perhaps even silk shirts and velvet blazers.


If you’re looking for your first date, download the Social Concierge app and they’ll have you covered!

Visit the website here: www.socialconcierge.co.uk

Download the app here: http://apple.co/2jZjvYi

Written by Andrew Mahiga from Social Concierge.