July 7, 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.

To save you from the pre-date jitters, we’ve enlisted the help of Vanessa Ho, 2017’s Face of Singapore Winner. Her Instagram is full of everyday fashion inspiration, and her fresh-faced look and girl-next-door charm make dressing up seem so effortless. Here are Vanessa’s picks on what to wear on a date.


Going to the movies

Movies are always a foolproof date idea. An escape from reality, and an opportunity to chat about the plot and characters can determine if it’s best to avoid scary movies in the future. You will never go wrong with a little black dress and remember to ward off the cold with a sleeved midi dress. Or you could cuddle up to your partner during the movie. Nothing better than sharing some body heat.

Vanessa: “Movie night definitely calls for a romantic comedy. It’s great for laughing and cuddling. I will describe my dating style as more of an independentist realist! I don’t want to spend time on someone who I can’t see myself with in the long run.”


Let’s play some games

Having a date that involves an activity like bowling or ice-skating allows you to see what your partner is like. When you are having fun, you need an outfit that is comfortable and flexible, so that you can break out into a celebratory dance whenever you win big. Trousers will always be a good choice and always remember to accessorise minimally, you don’t want restrictions getting in your way.

Vanessa: “I have been wanting to go on an adventurous date like hiking or to a theme park. There was once, I tried rollerblading with my date. But on that day, I did not put in enough effort to dress up because I thought it would be a casual affair—and my cheesy polo tee and below-the-knees pants would suffice. As it turned out, my date took it more seriously than me. From that incident, I learnt my lesson. It’s better to be overdressed than under.”


Sunday Picnic

Having a picnic is the ultimate summer date idea. The Singapore Botanic Gardens is a great place if you wanna relax and surround yourself with nature. There are even concerts by different orchestras during the weekends, so do check out the events page at NParks to find out more. For this occasion, wear something cool and relaxing. A simple silk blouse and a pair of shorts will do the trick. Match it with a stylish hat to fend off the heat.

Vanessa: “Idea of a perfect date? A simple dinner and then a heart-to-heart talk while walking on a beach.”


Cafe Hopping

It’s has been repeated one too many times that Singapore’s unofficial national pastime is eating. Why not kill two birds with one stone by combining dating with eating and cafe hopping? When you are on a coffee date, you do not want to risk over or under dressing. A simple pleated dress as seen on Vanessa will seal the deal. Remember to wear a comfy pair of shoes, because some cafes are quite secluded, so be prepared to walk.

Vanessa: “I don’t believe that a guy has to pay on dates. If he has the ability, go ahead. Otherwise, I am okay going Dutch. I am often mistaken for someone who is stuck up and unapproachable but if you know me, you will realise I am quite the opposite.”


Fancy a tipple

Going for drinks is the best way to break the ice and get to know someone new—alcohol does help to let your guard down. After a pint or two, head over for a walk along Marina at Keppel Bay or the Outdoor Gardens at Garden by the Bay (they close at 2am), and admire the dazzling Supertrees. Picking out an outfit for a drinks date can be challenging. You don’t want to appear too flirty nor unapproachable. It’s always great to accentuate your curves by matching solid colours with patterns. As shown on Vanessa, a simple dual coloured racerback top and bold patterned pencil skirt might capture your date’s attention.

Vanessa: “Sometimes wearing a jacket can add an additional oomph to any outfit. I will recommend going to Ce La Vie at Marina Bay Sands if you want to go for drinks. The fantastic skyline of Singapore just makes the whole experience much more enjoyable.”