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What to Wear on a First Date, According to the Experts


Finding someone to go on a first date on can be tough with our hectic lifestyles. Why not take the hassle out of first dates by letting the experts set you up on one here?

When it comes to first dates, many singles are unsure about what to wear. In fact, it’s common for many people to ask themselves:

“What do I wear for the first date?”

We understand that meeting a total stranger or a brief acquaintance on a 1-1 date is stressful enough on its own. Let us help you ace that first date with an image coaching session by our lovely Image Coach, Celeste Bo!

what to wear on a first date

An Image Coaching Session with Jean, a Marketing Executive in her 20s:

Celeste: “There are many elements to consider when it comes to picking out an outfit that suits you. For example, is your skin tone warm or cool? This will affect what colours and makeup suit you.”

Jean (before)

what to wear on a first date

what to wear on a first date

Work Look: Jean (after)

what to wear on a first date

what to wear on a first date

Celeste: “Jean has a lovely smile – her smile would look even brighter if she wears brighter colours, and so I encouraged her to change from her dark blue top to a pale pink one to brighten her face. Also, it’s good to tuck in your top loosely, especially if your top is long. This will make your legs look longer!”

Date Look: Jean (after)

what to wear on a first date

what to wear on a first date

Celeste: “For a night time restaurant date with a bit more preparation time, a sultrier look can get you more attention from your date. Showing off your décolletage in a tasteful way is a simple way to look appealing with overdoing it.”

The Image Coaching Session Experience, in Jean’s words:

1. How was your Image Coaching experience with Celeste?

Insightful and useful, with lots of practical information. It helped me understand myself better in terms of what’s suitable for me, and that it’s okay to experiment with colours and clothes, rather than sticking to my usual dark-coloured clothes.

2. Do you think what you learned during the session is easy to pick up on your own?

As I am not trained to pick up little details and to apply them on myself, I would have to say no. While image is a subjective topic, there is a certain standard to adhere to when it comes to looking your best in the eye of the public.

As a trained image coach, Celeste let me know what suited me without being biased about my preferred fashion sense, which I appreciated.

3. Out of the 2 looks that you tried out, which one is your favorite look?

The work outfit version. It is something very different to what I normally wear, but I am quite taken with it. also think it looks very elegant, and would be a great look to go out on a first date that takes place after work!

4. On a scale of 1 – 10, how would you rate the overall experience for this session?

9 – Celeste is very thorough; she even trimmed my eyebrows and put a lot of care into the littlest details. It felt motivating, too!

5. Was your coaching session fun?

Yes, I thoroughly recommend everyone to try it out – they may be surprised but they learn about themselves!

Celeste’s Biography

what to wear on a first date

Here’s a little more about Celeste, and why she’s qualified to help you find an image presentation that suits you:

With nearly 15 years of experience with Singapore Airlines, Celeste has the expertise and experience to help you create an image that is aligned with your personality and stylish at the same time.

She is a trainer who possesses the Advanced Training and Assessment (ACTA) certificate. She has also undergone rigorous training at the renowned Style Coaching Institute.

With her professionalism and enthusiasm, a session with Celeste will guarantee you an interactive, fun, and impactful makeover session that brings out the best in you.

Celeste’s role is to guide you from start to finish, by designing simple and highly personalized image strategies for you to create a favourable first impression.


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