Where Does Confidence in Appearance Come From?


Rosina wrote me this question:

My style question is one of confidence.. I think I alluded to it once before. I really think I have a style: Jeans, boots, long tops, my own jewellery designs, huge purses, arm warmers or opera gloves, and lots of texture. However, I never, ever, EVER feel confident. If someone looks at me, I think it’s because I look like a wreck, or I have a smut on my nose or something. Once, I was sitting in a shoe shop and I saw a lady from behind in the mirror opposite, and thought, “Wow! I wished I looked like that…” and then I realized it was me.

I tell you that story to illustrate how hugely UNconfident I am in my appearance. I told my husband, who was there with me, and he just shook his head in bewilderment. When I have a business appointment, which is blissfully rare, I feel really fearful. Being tall (almost 6′ in heels), I walk really tall and strut my stuff, so I look as if I am the world’s most confident person but inside I’m dying in case they are thinking how ridiculous I look. What’s with that? Part of me says it’s insane but the other part caters to it.
Do you think that confidence in one’s outer appearance is a learned thing?
Wow – I have to tell you this made me feel so sad, and I wish I had some sort of magic wand that instantly gives confidence (and I’d use it on myself as well!).


I do see a lot of women who lack confidence in their appearance, they often don’t feel like they own any ‘style’ in particular – though this doesn’t seem to be Rosina’s problem unless the style she has adopted is not really her from the inside out (and you may want to read her story about her style here which she shared after this post was written)

Looking Inwards or Outwards?

One thing I have learned over the years is that most people are more inward than outward focussed, so they’re spending more time worrying about what they’re wearing rather than thinking at all about what you are wearing. You notice and remember what you wear (others may not be as aware).
Rosina’s comment also made me wonder about growing up and if anything incidents in her formative years might have brought about this lack of confidence – she writes:

My parents both said I was lovely. I never believed them and used to cry when I was at elementary school because I wasn’t at all pretty and everyone let me know that. I dreaded school. Also, I had to wear these strange clothes that my mum knitted…skirts with braces and similar horrors. However, after this, my schools had a uniform. I don’t remember feeling bad about the way I looked then.

So the hand-knitted/home-made clothes didn’t help Rosina feel confident at school, whilst the school uniform was fine – what I’m picking up here (and I could be quite wrong) is that when in a ‘uniform’ Rosina feels fine and confident, it’s only when she’s in her own choice (though back then she had no choice as a child) she lacks confidence.

So where does confidence come from? What I’ve noticed with my clients is that it comes with knowledge – the more they understand about who they are and what suits them, the more confident they feel. This has also been true for me on my journey of style.

How to Feel More Confident in Your Appearance

1. Discover who you are as a person – what are your unique set of personality traits? How can this be expressed by clothing and accessories?

The reason I was so keen on spending 3 years of my life researching and developing 16 Style Types (with Jill Chivers and Jane Kise) was that I knew at my core that personality is the key to feeling confident in your style.  There is a direct correlation between personality and how you approach style – such as whether or not a capsule wardrobe is for you, or if you want to look like others around your or feel more comfortable looking more different (plus lots more which you can discover in your Style Type Report).


where does confidence in your appearance come from? How to look and feel more fabulous every day
This winter coat always makes me feel fabulous ( and I always get a bunch of compliments on it when I’m wearing it), plus the white column of colour is a great and stylish way for me to express my casual style.


2. Which of these traits do you want the world to pick up on when the meet/see you? How would you like to be perceived by others?
The first step in my 7 Steps to Style program is all about how to express your personality through your clothes – it gives you the language and tools to help you share with the world who you are – which clothes, details, accessories, patterns and prints, colours and fabrics – are the right ones for you. It’s the other half of the personality story.


3. What is your lifestyle? What do you spend your time doing? What clothing is most appropriate for the activities that you undertake?
Another step in my 7 Steps to Style program is helping you understand your lifestyle and what you actually need in your wardrobe (so frequently we don’t have “the right” clothes for activities and occasions that crop up in our lives).  Creating a useful and relevant wardrobe that is future focused (so many women have wardrobes from the past that are not helping them today or tomorrow) is something to strive for.


Where does confidence in your appearance come from? How to look and feel more fabulous every day
A statement necklace has become part of my style – they make me feel like my outfit is complete
4. Style formula: add 1+2+3 = 4 How do you relate that inner you (personality), with how you want to be perceived and what fits with your lifestyle? When each element comes together, that is when confidence grows.
The more you know the more easily you will discover and develop your true authentic style.   The feedback I get from women who have discovered their style is that they feel empowered and confident in a way they’ve never felt before.  They tell me that it has a positive flow-on effect into their whole lives that is more than just skin deep.


Rosina wrote:

I don’t want people saying I’m classically elegant, but rather that I have a different streak that makes what I wear interesting as well as tasteful. I’m not really explaining myself well, am I? Lol. A good example is today. I had a pretty burgundy and black small check long blouse on with a ruffle and a bow at the back. Both my husband and daughter, and my neighbour complimented this blouse and the whole look with indigo jeans, black heels and purse. I,on the other hand thought I looked like mutton dressed as lamb because of the bow and frills. So I voiced that and everyone shook their heads and basically asked me if I was nuts.

Here we can start to see a little of Step 2 coming in – Rosina’s clothes, even though they may have looked great to her family and friends, they weren’t a true reflection of the inner Rosina (Step 1), so she lacks confidence in her appearance.
This week I’ll be working through each of these Steps to Style (and confidence).
What makes you feel most confident in your appearance?
Were there any experiences in your formative years that either gave you more confidence or sapped it?

Confidence Comes from the Inside Out

Who are You ?

What do You Do?

7 Steps to Style - Discover More


I'm not sure if it's for you but how would you feel if you learned all about the colours and styles of clothing that suit your individual personality, shape and style? Just imagine what it would be like when you can open your wardrobe and pull together fabulous outfits that make you look and feel amazing every day? If you'd like to stop wasting money on the wrong clothes and accessories plus join an amazing bunch of very special women also on their style journey - then my 7 Steps to Style program is right for you. Find out more here.

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  • My family (especially my Mom) were hyper-critical of my appearance growing up, especially when it came to weight. To this day, my primary filter when deciding if I like a particular garment is "does it make me look thinner?" I have a very hard time wearing something that I believe makes me look heavier.

    My "uniform" tends to be black trousers or dark blue jeans, a tee shirt or sweater, and boots. For some reason boots especially seem to give me confidence. I always feel good in boots, whether ankle or knee length.

    It makes me sad too that we are often so critical of our own appearance and style choices.

  • When Rosina said she saw herself in a mirror and mistook her reflection for a well-dressed stranger, I understood that she has a real "disconnect" inside herself…When she sees her reflection she's truly having an out of body experience!

    One thing that really helps me with confidence in dressing is PHOTOGRAPHING myself in borderline looks, just to be sure. This really helps me see myself objectively and assess if I need to add something or remove something.

    When we are kids and are teased, we learn to do ANYTHING to avoid that pain, and that means dressing to avoid ridicule, whether perceived or real.

    Once I choose my clothes, they help me act the part I want to express that day. When I have on the costume, my identity and my image merge nicely.

    I hope dressing is a joy for all of Imogen's readers. If not, take baby steps and read the posts to follow.

  • I live in the US and have a split wardrobe–typical, contemporary Western clothing and also Indian clothing (salwar kameez) that I wear when in India or here, once a week or so, for cultural events.
    For years, I have felt prettier in the Indian clothes and received compliments even though they are technically modest, and wondered about that. Then today I realized the neckline of the flaring kameez tunic I wore perfectly accented my heart shaped face, and I love ornamention of fabric–the embroidery, gold thread and or/sequins, and fluid fabrics. The salwar pants could use a bit of shaping to make me look taller, I realize. These are unfortunately cut one-size-fits-all with a drawstring waist!

    It is NOT FUN to spend money on clothing and not go about enjoying it and feeling good about oneself. I would like to move the same excitement I feel when I put on Indian clothes and a bit of makeup to the everyday Western me, too.

  • A tiny observation, which may not have anything to do with Rosina's experience, is that sometimes children can experience their parent's approval as insincere if it doesn't come with enough objective detail to seem honest. For example: "you're so cute", "you're perfect", "you can do anything", none of those help a person to develop a healthy sense of individuality; not like a more specific compliment does.

    I still struggle with this in alot of other areas, but as I learn more, I enjoy alot more confidence in my appearance. 🙂

  • They say the first step to change is recognizing what you don't like. Seems Rosina has articulated her feelings very well. In self-expression, I'm sure she will start to see opportunities to change her attitude. She obviously wants to change – and knows what she wants to change.

    When people tell me I look nice I opt to believe them. Maybe that's super simple, but it works for me. And I love telling other people what I love about their outfits and style. Makes me more aware of how many ways there are to be very chic. That combo has helped to cement my confidence.

    (Of course, there are times when I feel like a total wreck – but I just buck up and wear lipstick and hope no one else notices.)

  • One other thing – just went to check out Rosina's lovely blog and saw a photo (of her eyes only!) and I can see that she's gorgeous – categorically. I'm amazed she doesn't feel confident. I'm sure your posts this week are going to turn her self-image around, I!

  • Gosh… I appreciate your comments so much, Imogen (and Karen, et al).

    Yes, that whole disconnect thing is definitely apparent. I was seriously envying the "lady in the shoe store." Rebecca's comment also rings true. I remember KNOWING that I was not at all appealing to classmates. I was constantly called ugly and told my nose was huge, my eyes were odd, my face was fat, and so on (all of which were true)…so when my mother raved over how "beautiful" I was, and I knew I wasn't, I just grew to mistrust her. Perhaps significantly, when Don compliments me, I die a bit inside because my instant reaction is that he is lying to make me feel good. (Goodness, this is like a therapy session, lol!)

    I'm determined to get on with it though and to stop being ridiculous. What I find amazing is how much we are shaped by our childhood emotions. Often for the rest of our lives.

  • Yes, for me confidence about style comes from understanding much, much more about proportion, balance, clothing construction, and fabric qualities than I ever did.

    For many reasons, I was very conflicted about "getting in the game" and so 99% of the time I opted to just throw on whatever random item I'd been given or bought on sale.

    By my mid-30s I really think very little worked!

    Once I decided to figure out how to enjoy clothing on a personal rather than theoretical level (I'd always been a big design history/vintage fan) and started learning the above I felt a lot more control.

    Really assessing my own shape in a very detached way so that I could figure out what styling "tricks" I wanted to employ actually made a huge difference for me as well.

    The general body love stuff wasn't working for me (probably because I am oppositionally defiant!) but having to evaluate how the parts made up the whole freed me to be much more dispassionate about some of those parts, ha. More "Right, why don't I gloss over THAT and celebrate THIS" and less self-punishment.

    [Come to think of it, it's like when I gave myself permission to hate exercising, but required myself to exercise Just Because. It felt great to say, no, I DON'T have to love every body part — but I have to accept it Just Because.]

    While I'm trying to add clothes with a bit more personality, I almost always feel really good in what I wear. I walk away from a lot of clothes– and shoes! — I love because they don't meet my standards for flattery.


  • I think that confidence in appearance comes from your childhood ; the way you were ( or were not ) treated. You carry this gift ( burden ) with you the rest of your life. If you carry a burden, you never are happy/confident, unless you decide to do something about it! For me, that something was psychoanalysis, and I learned that many of the things I suffered from ( also my looks ), actually were things, my mother herself had a complex on. She had transferred her own fears on to me. Luckily I have become aware of this all. My mother had a complex of her height, and automatically thought that I would too. Today, however, I love high heels, and am only having a bit trouble balancing my way with them.

  • It's sad to read those things about Rosina, but I'm recognising myself so much within that! Whenever it comes to matters of style in conversations, I get complimented on the fact that I always look put together / have a style, or to rephrase what a friend of mine (who is an art history student and really has an eye for detail): you are one of the rare people that I like to look at because you are dressed well on a daily basis.

    Unfortunately, I can't embrace the style I'd love to have (classic french chic with a little modern edge… it's just not working on an 8-shape body that's NOT really toned…). Unfortunately, I too have been mocked for years and years for being fat and ugly.
    Today, I'm better at taking compliments and accepting that I, too, can be pretty. But on many days, I just still don't feel comfortable within my style.

    Thinking about the points you mentioned, I think it's because on these days, I'm not me. I'm not wearing what is most appropriate for my body / lifestyle / to express myself. I'm awaiting your next instalments and then will hopefully be able to finally get rid of these doubts.

    … sorry for rambling…

  • Deja – thanks for your input – I'm sorry your mother was so critical.

    Karen – great thoughts – I think most of us have had this disconnect sometimes.

    Anon – interesting how you feel prettier in your cultural dress rather than western dress.

    Rebecca – interesting – the difference I got from my parents was – they still said "you can do anything you want" but added the clause "provided you work hard for it"

    Kline – great advice

  • Rosina – How sad that you find it difficult to even take a compliment from your husband! You are gorgeous – I don't understand why you think you're unattractive (from the photos I see on your blog, there is NOTHING wrong at all with you and your looks!).

    Vix – thanks for your advice.

    Metscan – great to hear you're getting over your mother's issues!

  • Imogen, the crazy thing is, I can look in the mirror quite objectively and think I've done a good job. However, it's when I get compliments or see others looking at me (even my husband), that the overwhelming fears/insecurities take over. However (and this is a big however) I have noticed that when my daughter compliments me, on her own such as when we go for a coffee together, I can take that compliment and BELIEVE it. If my husband were with us and jumped in with, "Yes, you do," I'd think "Yeah, sure…) Of course, the only reason looking good is so overwhelmingly important has rejection at its roots. I should write an essay on this one. Lol!

  • If a woman (not Rosina, anyone) is
    1. Deeply dependent on the approval (not appreciation, approval) of others to feel OK
    2. Has perfectionist tendencies- things are never good enough or quite right, and
    3. Bases most of her sense of self-worth on her appearance,
    she is a sitting duck for shaky confidence.

    I am always confident in my favourite real jewelry, it is talismanic for me.

  • I think some of this comes from the way we as women fit the cultural icon of prettiness. The thing that may be counter-intuitive is that when we fit that stereotype, other insecurities will flood in if we are prone to self-doubt. I grew up fitting the stereotype, blonde, thin, symmetrical features. In fact I was besieged by feedback on my looks. Guess what. I didn't really derive comfort from it and just floundered around in a whole host of other insecurities. I'm way less pretty now and way more confident. I forgive my 52-year old wiggly belly in a way I never forgave my 20-year old pretty dang great thighs….And it's only confidence about my self as a whole that lends confidence to my feelings about my appearance.

  • I really think real confidence also comes from inside and from other needs. Sometimes a too self conscious image tells much about the lack of confidence of a woman, she tries to repare an inner wound something from the outside. When I feel really confident I forget about it. A day I am happy and confident enough makes me creative and satisfied while dressing: I am more darefull and playfull, and I don't really care wehat other poeple think. And it works! It's usualy a success. The oposite is less about to happen. I live in a country where machism is strong (Argentina) when I come from Quebec, Canada, where feminism movment has been one of the strongest in the world. My interpretation is that here, as a wrong response to machism emerges this image of a "strong" woman gone trough many plastic surgeries, still very sexual at 65…It is the country of false tits (maybe because they show them?).I think woman's lack of self confidence has deep cultural roots.There is still so much to heal, colectively! Personnaly I find that if I invest too much preocupation (in a compulsive way)on my appearance, The result is that I get "unplogged" from inside. If I spend too much time in the wardrobe I can hace a little panic attack or start to sweat. Imogen tought me almost scientific knowledge I use in orther to be more effective and less "wondering", new preocupation as I got older ( 48). But I know I have to balance my life and that the voice who telle me I look bad is the little sabotage voice we all have inside. There are ways to get rid of it and this path is about healing the inner creative self who is also the inner child. A great reading: Julia Cameron, "The artist's way", and all her books!

  • I just read for the second time my last comment and want to apologize for my bad english wich is not my first language. I realized it made me write things I dont think, and made my text hard to read. I am sorry, I'll pay more atention to my faults. I hope I have been undrestood despite this.
    A couple of ideas: I read the sinuous line is te nicest one to the human eye.

    Makes me feel confident from the "sensation" point of view.:

    Instead of stifness, Movement:
    -Luminous hair I can wear free with no accesories.
    – Weight in the lower part: Wide pants or dress, boots.Grounds me.
    -Bangles. (little music)
    -The sinuous line of a
    colorfull scarf.
    -Long lines: long gloves or sleeves thalf cover my hands.
    -clothes tailored and with waist but that allows the belly to be relax….

  • Rosina – I think that you need to nip your negative thought patterns in the bud – replace them with new positive thought patterns – so instead of your brain going down the same negative trail whenever Don compliments you, stop yourself, and think a positive, such as, Don is a great guy, he has good taste in xxx, which means that his compliments are valid and real and I will just say "thank you".

  • Duchesse – good points. Having to seek the approval of others for your own wellbeing is not the best way to have confidence.

    LPC – I'm glad you've grown into your confidence – I think in many ways often confidence is something that increases as we get older and 'know ourselves' more. When we are young we don't really know who we are and are searching more.

    Anonymous – don't worry about your English – we understand (and I guessed that it wasn't your first language). Thanks for sharing your great ideas.

  • Imogen, it's her third language (at least). I understood her perfectly, as I speak French far more often than I speak English, and speak both Italian and Spanish.

    I had a similar experience to pseu of a "toxic mum" (herself probably abused in childhood by a tyrannical father) who came across as a perfect lady to everyone else.

    There are a lot of things I just won't wear, and I sure as hell won't wear a swimsuit, although I've lost weight of late mostly though doing exercise that didn't require so much skin to be shown. Pity, as I loved swimming when I was younger and slimmer, and it is a good and healthful exercise, but I refuse to look disgusting.

  • Whilst Rosina has since written to say that Imogen was spot on in her analysis, I slightly disagree with something Imogen said.

    If you feel psychologically uncomfortable in your clothes, fearing that you look like mutton dressed as lamb, it MIGHT be, as Imogen said, that your clothes are not an accurate reflection of the inner you. But it might not be that. Because sometimes, for some of us, the inner me is young, exciting, edgy, like the clothes we would love to wear.

    The problem is that our age/wrinkles/weight fail to reflect our inner self. These things are bad luck, or at least not easily within our control. They really are nothing to do with the inner us.

    In such a case, how is one to dress? If you 'dress your age', you feel as though you are wearing your granmother's clothes, and that feels depressing and also violates Imogen's idea that you should dress in a way that reflects your inner self.

    If you dress in a way that reflects the inner you, you can STILL feel uncomfortable and like mutton dressed as lamb, because of the clash between the inner you and your chronological age or weight or whatever.

    Rosina may have found a way to feel good about wearing less young clothes (and the new look certainly looks fantastic!) but for many, resolving the clash between the inner you — your soul, the real you — and the body and face you did not choose and can't change, is a nontrivial task.


    P.S. Rosina, have you given up the opera gloves and arm warmers? I am curious to know how they fit in with your new elegant, slightly more mature, less edgy look.

  • Hi Sarah,

    A very thoughtful comment. Interestingly, I no longer feel that lack of confidence. I haven't changed my wardrobe considerably either. There were three or four items I hated and all had bows or frills. These items impacted my whole sense of me as I disliked them intensely and the fact I had actually purchased them threw my confidence in being able to choose something right for me.

    As soon as I figured this out (and it had nothing to do with picking clothes that were to young for me), I have overcome this issue and love the person I see in the mirror.

    I fully agree with everything you have written about feeling young inside and so choosing clothes that reflect that. Why not? For the record, there is no "new mature me." I am who I am, love that, and continue to wear opera gloves, armwarmers and deconstruction. I will always be an artsy girl inside, wrinkles and all. If others have an issue with that, Tough beans! R xox

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