July 20, 2017

Dressing up for a date can be absolutely nerve-racking. Whether it’s the first or 100th date, the mere thought of wanting to make a good impression always gives me flutters in my stomach. For most people, the perennial question of “What should I wear?” is always on their minds, but with some advance planning and well-chosen, occasion-appropriate outfits, you will never have to panic anymore.


Coffee or Tea

Meeting at a cafe is less pressurising than having dinner, because you can cut your date short if the connection isn’t there. Build up your coffee knowledge beforehand and impress your date with some humorous fun facts. Smart casual is the way to go.

Sheena: “Girls love it when guys have a sense of humour. I still remember catching Pokemon on my first date and looking silly running after ‘rare’ species. During another date, while we were on the way to the car, bird poop fell on my head. And my date jokingly made a comment that we should buy 4D! If I’m going to a cafe, you will probably spot me in a simple top and a pair of shorts with my Adidas sneakers.



A staycation is a great way to pamper yourself and your other half. Plus, you don’t have to travel far. A 2D1N weekend holiday in town or a 3D2N boat ride to the neighbouring island can be a great getaway. It’s time to bust out your summer looks.

Sheena: “I have always wanted to go scuba diving, as there’s so much to discover underwater. I do enjoy staycations because it’s a great way to recharge—nothing beats chilling by the pool or lounging on a hammock. A flowy off shoulder top with denim shorts is not only comfy but also Instagram-worthy.”


Going to the Museum

Going to museums can be fun and educational, and also a great way to avoid the sweltering heat. On a date like this, you would want to dress smart but not go overboard. A classic shirt and jeans as seen on Sheena will be a classy choice and don’t forget to bring a jacket if you get cold easily.

Sheena: “Visiting museums is one of the things I love to do on weekends! Usually, I will wear something playful like a graphic t-shirt with ripped jeans. To add a feminine touch, I will put on a sweet pink leather jacket to balance the outfit. I’m very big on staples simply because it goes with anything. You can pull off a statement jacket or a quirky pair of jeans with a basic tank top any day.”



Going to watch a musical or play can be entertaining. A good way to build rapport is to exchange opinions on various cast members or even the plot. Just because the theatre is a dark place does not mean that you do not have to dress up for it. One great tip is to keep it minimal, but make sure you have bold accessories like Sheena’s fur bag as seen above.

Sheena: “It’s important to be engaging. There was one time, I was texting on my phone so much that I accidentally followed my date into the male toilet. Luckily, there wasn’t anyone around! For a more elegant feel, I will go with darker tones like how this bold floral embroidery stands out against the black choker top. Pairing it with a pleated skirt or skinny jeans is typical but if I’m in a daring mood, I will wear it fishnet stockings and a mini skirt. Before heading out, I’ll spray a hint of my favourite scent, White Tea from Elizabeth Arden and I’m ready for the evening.


Theme Park

Let’s be honest, festivals and theme parks take the excitement to the next level. The rules of dressing are simple; just wear a comfortable pair of shoes.

Sheena: “I will highly recommend going to a trampoline park. I went to Bounce Singapore recently on a double date and had such an amazing experience. I really want to go to Disneyland. And I know what I’ll be wearing: my outfit has to last throughout the day, so comfort is key. Personally, I will wear a sports bra underneath my oversized denim jacket with a skirt.