If you’re planning on a fancy dinner at a nice restaurant, this is a given. A long sleeved button up shirt is a must. However, if the plan is a casual brunch and movie after, we recommend a short sleeved collared shirt. Wearing a t-shirt on a first date might make you look sloppy, which is why a short sleeved button-up shirt is perfect for a casual date in our tropical weather.
By comfortable, we do not mean flip flops. You might end up walking alot, so it’s best not to break into your brand new pair of brogues which might turn out to be uncomfortable.
Quirky printed socks and suspenders are great ways to accessorize an otherwise plain outfit. It’ll show that you have a good sense of style and you’re not afraid to explore fashion-wise. A sleek watch is also an essential accessory that can smarten up your ensemble.
Make sure you’ve had a clean shave (if you have a beard, at least ensure you’ve trimmed it) and a good haircut. Dirty and long nails are a huge no-no as well. Nothing is more off-putting than a sloppy looking man.
Yes, we know you’re supposed to “dress to impress”. But is it really necessary to wear a three-piece suit if you’re only going for dinner and drinks at a roof top bar? Dress appropriately for the location and activity you’ve planned for your date. A good option for a semi-casual date would be to throw a denim jacket over a printed t-shirt.