How to gain confidence in YOU and your style?

by Sylvia

How to get confidence in you and your style |

I talk about confidence a lot on this blog and how important this factor is to look stylish and comfortable.

But how can you gain that confidence and show it off to the world?

Let’s start with a personal story

When I came to Singapore about 9 years ago, my style was very casual.

Coming from The Netherlands, where the dressing sense is practical first and foremost and then 7 years in Australia, where casual absolutely rules, my wardrobe was filled with t-shirts and 3 quarter pants. I had no handbags apart from 2 or 3 practical backpacks and no heels.

I kind of got by with that until I moved to Singapore and started going out more and attend events.

I can still intensely remember this one event.

Me and my friend visited a fundraisor and I thought I was appropriately dressed in pants and a nice top.

my neighbor disagreed.

“Don’t you have another bag to bring?”? she asked.

“What’s wrong with this one”? I exclaimed. I had brought a fancy backback from a Dutch designer and thought that would do just fine.

In hindsight I realized I looked very out of place. Too casual, and a proper handbag would have been much more appropriate.

I realized I had my style slide a bit too much.

As a busy mum who was also working, shopping hadn’t been a priority.

I decided that it was time for a change, so I started looking at my friends and what they were wearing.

They dressed a lot in spaghetti type tops with embellishments. Soon I had quite a few of those as well.

However, it soon became apparent that I did not feel comfortable in those tops. They highlighted my bust and upper chest, which is an area I like to downplay.

The style was also much too revealing for my taste and I was cold half the time indoors (where there is too much air-conditioning).

I did not feel fabulous in those tops at all! I realized, I had copied someone else’s style and hadn’t really paid attention to what suited ME.

It took me a while to figure out what I liked and what suits me.

When I finally realized this, I started paying attention to what my style was and which clothes I felt comfortable in. Slowly but surely I discovered what made me look and feel fabulous.

I started to feel much more confident in how I represented myself. Going to events and meeting new people was no longer something I dreaded. I enjoyed shopping again and had fun with fashion and style!

Style quote from Iris Apfel |

Here are some of my tips on how to get confidence in your style and way of dressing and how to figure out what is right for you

Get to know what YOU like

Record how you feel when you wear certain items. If an outfit does not make you feel confident and fabulous, then it is not the right outfit for you and you should either think about wearing the components in a different way or donate them.

A lot of confidence comes from knowing who you are and what you like. For any clothes to work for you, it is important that they suit your style personality.

When the clothes suit you as a person, this will come through in your confidence levels. You could start by taking this quick and fun personality quiz.

Get to know your body

Another factor is knowing what suits your specific body. When you choose clothes that you know will fit you and make you look better, you will automatically have more confidence. You can start by figuring out which body type you have.

Then start thinking about those parts that you like about your body and want to highlight. Also know those parts that you want to downplay. Choose those clothes that make you feel good about yourself.

Notice what delights you

Start noticing and writing down what delights you in the clothes of others and then start adding those elements to your own wardrobe.

Take a few risks

It’s impossible to grow in terms of style if you never try something new or step a little bit out of your comfort zone. When you have noticed what you like in the style of others, apply some of those components to your own style.

Do it in small steps though. If you feel that you get happy from seeing more color on others, start adding a scarf or belt.

Then, when that feels good and makes you feel happier about your outfit and more confident, do some more of it.

Fake it!

If you don’t feel very upbeat or confident on a particular day, you can fake it!

I know that when I know I look good, I can pretend I have a lot of confidence. That is why it is especially important that I look good for important business meetings or when I need to do a presentation. Knowing that at least I look very presentable, is giving me a boost. 

If you feel like you have ‘nothing to wear’ on a day like that (which usually happens when you’re feeling down) choose an outfit which you have worn before and that you know you felt great in.

style quote Rebecca Sonit |

I’m now dressing like ME and it shows

I never wear those spaghetti straps tops anymore that show cleavage.

I have found my own signature style, like draped fabrics, asymmetry and cigarette pants.

I embrace color, silk, accessories and shoes. Backpacks are a thing of the past.

I feel I have come a long way in terms of style. I know and understand myself and my style so much better and as a result look and feel so much better.

Want some help feeling fabulous in 2019 too?

In 2011 I created 40+style as I realized there were more women like me who at one point in their lives had lost their style a bit. I had learned so much on this topic and was so successful with it that I wanted to share my knowledge.

Soon, I created a style course that has helped thousands of women find their style. Want to be sure not to mis the next course? Get more info here.


Find your style and get confidence |

Right now I’d love to hear from you? Do you have confidence in your style?


{ 33 comments… read them below or add one }

1 Tracey Jennings

A very important part of developing style is what makes our heart sing and is as individual as we are! When putting outfits together when I get that ‘Sassy” feeling that says Tracey, I know I’ve hit my stride. Color, patterns, skirts and shoes all play a big part of that. A fabulous topic of conversation, Sylvia!


2 Sylvia

Yes well described Tracey!


3 Lisa

Really my blog has increased my confidence, because I had to think everything through, and then I had to really examine the evidence:).


4 Sylvia

Yes a blog really helps. I know it has helped my confidence and style as well.


5 Violet Pastille

I like this post. The thing with the strappy, embellished tops resonated. (And the A/C. Team Penang in the house) the whole thing resonated, in ways that I will have to think about more deeply.

But mostly: I know I am a magpie. And I will grab what catches my eye. So I have to be intellectual about where I put my eye. I other words, “I will become what I look at”.
Some people have a more firm taste parameter. Lucky thems.

What gives me confidence, (or recklessness) is a feeling that “Whatever the mind can believe and concieve, you will achieve.” I know this is a Napoleon Hill quote, but I prefer it as sung by Salt n Pepa in “Body Beautiful”. The best getting dressed song ever! Talk about confidence!


6 Sylvia

Thanks for your feedback. Salt n Pepe brings back memories. I went on to listen to that song. Indeed very inspirational. If anyone else wants to listen it’s here:


7 Patti @ NotDeadYet Style

Great post, Sylvia. I will remember this tip especially: notice what delights you. xo


8 Sylvia

Yes, that’s a good one for everything in life!


9 Rebecca

It is really amazing what a confident attitude can achieve in terms of style as well as life!
Lots to think about in this post. In my past life in the corporate world, I would try to fit in by wearing what my best friend called the “Miss Pendleton look” instead of embracing the more dramatic/classic look that really reflects me.
I also wanted to mention how much I love the illustrations that the very talented Anja does on your website.


10 Sylvia

Yes, it is so important to do what resonates with YOU. That is why noone can really tell you what to wear. You will need to discover that for yourself.
I agree with you with regard to the illustrations. I think that this one espcially is just fabulous! (another one coming up this week!)


11 Lizzie

I agree, you have to be comfortable in your own skin, while almost at the same time take risks. Think outside the box. Like when I wore a yellow camo shirt from Old Navy or Gap, I forget, and yellow capris. I learned that day that too much color is too much color. It became evident when my daughter shook her head and said, “No, Mom. What were you thinking?” Regardless, I pushed the boundary, failed, but pushed the boundary. Sometimes it takes trial and error to know what works for you!


12 Sylvia

Well done Lizzie for pushing that boundary! You only learn through experimentation.


13 Ann

Yes it’s about feeling comfortable in your own skin. I’ve worn many different styles over the years. I guess my clothing has changed as my life has changed. The tops with small straps, I never wore them either even when I was young. They always felt naked to me. You make some good points in this post especially about taking risks. You always look comfortable in your outfits.

blue hue wonderland


14 Sylvia

Thanks Ann. Yes being comfortable is one of my style elements. More about that later this week.


15 Christy

Hi Sylvia, Confidence is like loving oneself with flaw and all. Clothes do help to boost ones emotion but not for long. One must start loving from within to start loving without. I watch on TV of a women being disfigure and yet she exudes so much confidence, her scared face shines with beauty i can only wish is mine : )


16 Sylvia

I totally agree Christy. This is a much larger topic than what I can discuss in one article. But clothing and style is one factor that can help with confidence which is what I have tried to address here. It can help accept yourself as you are, ‘flaws’ and all, because you learn to dress your body in a way that pleases you. Loving yourself just the way that you are is the ultimate goal.


17 Alice - Happiness at Mid Life

I totally agree that you should always wear what makes you comfortable and wear it with confidence. When you wear it with confidence, you can make a potato sack look great!



18 Lorraine

First of all can I just say what a lovely picture Anja has done for this article. My spirits lifted when I logged on this morning and saw it!
Secondly, everything you say is right. On Friday I went to a lunch with 11 other women and agonised about what to wear (too casual?/too dressy?/trying too hard? too young? too old? etc etc). In the end I plumped for my coated/waxed jeans that I bought after Christmas but hadn’t had the nerve to wear yet, plus my stripy tunic, shown here:
I arrived last and could feel all eyes on me but I feigned confidence, and you know what? I felt great!


19 Sylvia

Ah Lorraine, you must have looked wonderful. Pity you don’t have a picture of your outfit!


20 Greetje

Yes indeed… How about an upload to the Forum?


21 Greetje

I have always been a mix of extreem confidence and total insecurity. Funny how they can live next to eachother like that in my body. But by doing all the things you have mentioned, I came a long way. Especially the visit to a (good!) colour stylist and bodyshape stylist, helped me a lot. I suddenly knew why I always hung back that cute pink pastel jacket. Cause it made me look like death warmed up, that is why. And why I never liked that expensive, good quality coat. Because it made my shape funny as there was no waist in it. These things help. And the fact that I was taking photos of my outfits helped a lot as well. Apparently with photos you create a certain distance (more than a mirror reflection does) which you need to judge the outfit correctly.
I am in a good place now. And still making mistakes haha. Och well I am human.


22 Sylvia

Making mistakes is good. It’s often through mistakes that you learn. That goes for a lot of things in life. Don’t be afraid to fail or make mistakes. They move you forward!


23 Sonja

Some years ago I was given a dress (in fact it was a dress for dancing salsa), and I wore it on a New Year´s Eve party. On that evening I was complimented a lot on that dress by both – men and women (friends!). So I who had always thought that I looked awful in skirts and that there was no nice dress for my figure started to try on, buy and wear dresses at school, where I work. That was unusual (in Germany it´s often like in the Netherlands, esp. in the country: you wear comfortable, casual clothes, dresses maybe only on hot summer days). I realized that I got more attention,had a lot of fun, others paid compliments on me… this made me more and more confident!
Now I know a lot more about my body type, read (here!) a lot about style and fashion and now HAVE the confidence to try “new” (for me) colours, wear sometimes higher shoes… It´s fun and a new kind of …freedom …for me.


24 Petra

I just love this article and the feedback on having confidence. I struggle so much these days as I’ve put on weight from medication so my style has “evolved”. I used to be very classic with little straight skirts and simple tops, all colour-coded and generally black or navy 🙂 but now I seem to be liking more joyful colour and more flow’y cottons. I don’t like clothes clinging or even remotely close to my body (unless they’re leggings because my legs are my best feature!). I know what style tops suit me but it is awfully hard to find these shapes in the shops. However on a more positive note, I don’t mind as much as I used to what people think of what I’m wearing – I’m 46, I’m a mum, and I enjoy being a little bit quirky! Now – my challenge is how do I pass this on to my very unconfident 12 year old son?! 😀


25 Sylvia

Lovely to hear about your style challenges Petra. It seems that you’re right on top of them. As for your son, yes that can be a challenge. Mine has 0 interest in clothing!


26 theresa

It took me until I was in my late fifties to have confidence in myself and how I wore my outfits. Now I am seventy, and I think confidence comes from having the exactly right hi-heel shoe that is perfect under the exactly right leg length of a pair of perfect fit jeans.
I know I have found my style, when shopping with friends, they will say, Oh this is so you! or I can see you in this color. And they are spot on, its what I would wear, and the color is one I love. I usually wear one thing that totally delights me. maybe it a bracelet, or scarf, or a pair of perfect shoes. and that makes the rest of me shine….T.


27 Sylvia

Lovely to hear your feedback Theresa and great to hear you found lots of confidence with your style!


28 Anya

I’m so excited about building on my personal style that tells the world, “I’m here – and I’m happening!”


29 Sylvia

Sounds good Anya. Good luck and lots of fun with making it happen!


30 Ronna Russell

Insightful, as usual!


31 Audrey Meyer

I believe I got my love of style from my mother. Even though things were tight during the war years my mum always managed to look lovely. She was an expert knitter in those days and earned extra income producing beautiful garments which were sold through an agency. Recently after studying my family history I discovered that my grandmother and her sister, my mother’s auntie, were hat makers and dressmakers so perhaps it has come down through my genes! Whatever, I am now 80 yrs old and still fascinated with fashion in general. Over the years I have refined my own style but nowadays with an extensive wardrobe I tend to allow myself a seasonal outfit twice a year whilst at the same time donating or selling something I no longer wear.
I am a pear/hourglass shape, petite and enjoy wearing up to the minute garments. It is autumn in New Zealand where I live so I am looking at some new knee high boots and a fedora hat to take me through the autumn/winter period and I will add a new leather handbag to complement the look.
Sylvia I have been trawling the internet for years and have never come across a website like yours. What excellent advice you give. It is a pleasure to search through it. You have re-kindled my interest in all things fashionable and I applaud you for providing this wonderful service to women. Long may you continue to do so.


32 Sylvia

Thank you Audrey for your kind comments. Wonderful to read you are still having fun with fashion and that you enjoy the site!


33 Elaine

I always feel better when wearing my favourite things. Have some things I don’t like as much and can tell when I wear them. Fashion is just an inspiration, I love my style. Tend to boho, natural textures, much more colour nowadays and always jewellery, my weakness. Am 52.


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