How to have the confidence to wear whatever you want


green fit and flare dress with over-the-knee boots

“I wish I had the confidence to wear that!”

Lately I’ve had quite a few comments like this from people who want to wear a particular look, but don’t have the confidence to do it, for one reason or another.  Sometimes it’s a body confidence issue, other times it’s that they’re just worried about what the people around them will say if they suddenly break from the “norm” and show up at work in 5 inch heels, or a 50s-inspired dress, or whatever it is they’d really like to wear but can’t. Whatever the reason, though, the result is that they end up wearing clothes that aren’t really “them”, just so they can fit in – and that’s a real shame, isn’t it?

Now, I’m not necessarily advocating 5″ heels to work, obviously, and the 50s dress might not be exactly practical either, depending on your job. But I guess the first thing I’d say to the people who tell me they don’t have the same confidence I do is this:

Sometimes I don’t, either.

Quite often, actually.

I think it’s really easy to look at fashion bloggers – or anyone wearing something a little bit different to the “norm”, whatever that is – and think they must be bursting with confidence (or just be totally narcissistic), which allows them to wear whatever they want, without caring what anyone thinks of them.

We’re not, though.

What you don’t see in my blog photos, for instance, is the fifteen other outfits I tried on and then discarded, because none of them looked right. What you don’t know is that I’m only wearing that skirt because I was so bloated that morning that I was scared you’d all think I was pregnant if I wore the outfit I’d originally picked out. What you don’t realise is that while I was taking those photos, every car that passed me slowed down to get a better look, and I’m SURE I saw at least one person smirking in amusement as the sight of the stupid blogger twirling in a skirt that no one around here would even consider wearing. What I don’t tell you is that I sometimes wish the people who know me in real life wouldn’t follow my blog, because I worry about what they think of me, and am paranoid that when I’m not around they say things like, “Oh my God, did you see those photos Amber posted? She must really think a lot of herself, huh?”

What I’m trying to say here is that everyone feels like that at some point: even people who look confident, and seem to have no qualms whatsoever about wearing whatever the hell they want.

life is short, wear the dress

The second thing I’d say to people who wish they had the confidence to wear the things they love is that you can’t control what other people think of you, and, no matter WHAT you wear, there will always be SOMEONE who thinks something negative about it. The best you can hope for is that they’re too polite to tell you about it, and luckily, most people ARE.  If you’re gong to worry about what people THINK of you, though, then you pretty much have to resign yourself to never going out in public, because as I said, you can’t control other people’s thoughts or reactions. You could wear what you think is the safest, most boring outfit in the world, and I guarantee that someone, somewhere will think something negative about it. If that’s going to happen anyway, and if that’s the worst that can happen, you might as well just wear what you want, right?

So that’s what I do. I came to realise that the person who laughed at me from their car when they were driving past that time had probably forgotten about me by the time they’d turned the corner. And it’s the same for you, too. If you turn up to work wearing something radically different from your usual style, for instance, sure, your co-workers might ask you why you’re “all dressed up”  – in fact, they might make all KINDS of annoying comments. But it’s not like they’re going to spend the rest of their lives obsessing over your outfit, is it? (Er, if they DO, you can trust me when I tell you that they’re the weirdos, not you…)  The fact is that people think things about your appearance all the time: you just don’t know about it. Even when you’re dressed casually, people will see you, and they might make some internal observation about the way you’re dressed, sometimes positive, sometimes negative. You probably do it too.

The important thing to realise about this is that it really doesn’t matter. Unless people are actively insulting you, which is rare, there is no need to concern yourself with what they MIGHT be thinking. The knowledge that someone you will never see again MIGHT have spent two seconds thinking you were over-dressed when he passed you on the street is not an excuse to stop wearing what you love. And honestly? Most of the time, what you’re wearing is just not that important to other people – because they’re too busy worrying about what YOU think of THEM.

The other reason I finally decided to say ‘to hell with it’ and start wearing whatever I wanted?

Because life is short, people. It’s a cliché, I know, but after years and years of being too scared to wear all of the things I loved, I suddenly realised that one day it would be too late. There I’d be, looking back on my life, and one thing I knew for sure was that I definitely wouldn’t be looking back thinking, “Yeah, I’m so glad I didn’t wear all of those amazing dresses I bought! Dodged a bullet there, for sure!”  I’m pretty sure I’d regret NOT doing it, though, so while I’m not going to pretend I don’t have moments (sometimes LOTS of moments…) where I think, “OMG, everyone is going to LOOK at me, I wish I’d just worn jeans!”, I can confirm that, so far, nothing bad has happened as a result of wearing whatever I want.

In other words?

Life is short: wear the dress.

green dress and over-the-knee boots

how to have the confidence to wear whatever you want
Hi, I'm Amber, and I'm a full-time parenting/lifestyle blogger, and author of My Blogging Secrets, now available from Amazon. I live in Scotland with my husband, Terry, and baby son, Max, and you can read more about me here.

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  1. Amber I think the main reason I come back time and time again to your blog is the fact that your voice is so genuine and sweet. I love your sartorial sense of course, and combined with the ease and familiarity of your writing style, it feels like this is more two girls chatting over a cup of tea than a blog post, which is a very, very good thing! I’m now going to go and get lost in your archives for a bit.
    Becs xx

  2. I love this post 🙂 Learning to ignore the naysayers and do what the hell you want is great for the soul, be it wearing pretty clothes, collecting nerdy things etc. As you rightly said, life is too short 🙂

  3. Ha your timing is epic! I had a crisis of confidence this morning when I opened Bloglovin and three posts in a row featured neutrals, beige trench coats, navy pencil skirts, white blouses and blazers. They of course looked very chic in their well lit, outdoor professional photos and then I looked down at my grey skirt with mustard spots and bright red top and thought huh, you’re 33, maybe it’s time to dress a bit more like a grown up. Of course, in order to do that I would have to throw away most of my clothes!

  4. I think you are absolutely right. It is very easy to get into a rut and then to be fearful to get out of the rut because of adverse attention and reactions. I’m 7 months pregnant and my wardrobe has mostly consisted of dark colours as I was not willing to splash out a lot on maternity clothes and well it is winter so my cosy black and grey cardigans have seemed most appealing.. however I’m already nervous about embracing my ordinary colourful wardrobe again.. which is silly because I LOVE my colourful wardrobe. Life is too short… time to go find some of that confidence!

  5. “Life is short: wear the dress.”

    Love it! That’s how I roll 🙂

    And yeah, people often say things like “oh. Don’t YOU look fancy” or “ummm, why are you so dressed up?” etc., but the alternative is not wearing the clothes I love. And that’s not an option 😉

  6. I’ve been struggling with this whole concept regarding something else (not clothing) and I always return to these two quotes whenever I feel self conscious about the way I look:

    “Be who you are and say what you feel, because those who mind don’t matter and those who matter don’t mind.” -Dr. Seuss
    “You can never be over-educated or over-dressed.” -Oscar Wilde


  7. Once again, you have captured my thoughts exactly. As Becky said, you are just so genuine! As an introvert amidst the confines of high school, I found it really hard to break out of the jeans and t-shirt rut because I didn’t want to address the “why are you so dressed up?” questions. College was very freeing in that I suddenly felt like I could wear anything. Then, the professional job started and I was afraid of wearing a skirt and looking too feminine in a male-dominated field. I thought I had to wear all dark neutral business suits with pale blue shirts just so that I would be taken seriously. At some point, though, I branched out and begin wearing brighter colors and skirts and dresses and I felt so much better for it. Yes, people did comment here and there, but for the most part, I think it was due to curiosity more than anything. People tend to be intrigued by the person that doesn’t look like everyone else and there’s a sense of mystery to it that they want to understand. There will always be those that are mean just for the sake of being mean, but it’s not worth basing what you do in life around them.

  8. Completely agree with everything you say here. Also it helps that when people catch me twirling in a public place while my boyfriend snaps me like the paparazzi, I simply convince myself they’re trying to work out if I’m famous and when they obviously can’t place me at all, think it’s their fault for not being cool enough 😉 and likewise if there’s no camera, I like to pretend they feel bad for not looking as awesome as me… Or something. It does kinda help to think if anyone is feeling negatively towards you, it’s their problem for caring, not yours. Most of the time it probably is more of a reflection of their own insecurities than yours…

  9. Lovely honest post that really hit home with me. Thanks! You are absolutely right, as usual – what random people think of your outfit is irrelevant to your happiness, and it’s always good to hear it once again.

  10. I was a goth for fifteen years before I started in wearing colour again. I got comments about wearing black all the time, as if it was a moral choice.and not a colour. Now I get comments about not wearing black enough (!!!) and about being too dressy… no one is ever pleased. On the upside, having strolled down more streets than I can count in corset and pvc boots and had to deal with the resulting yelling… I really just don’t care what people think. Most are just dicks who have very narrow world views.

  11. My friends love dressing up in full-era 50s and 60s clothing and they always get asked annoying questions but I love they way they answer.
    “Why are you ladies so dressed up?”
    “It’s Tuesday” or
    “Well it’s pretty inappropriate to walk around naked, you see.”

  12. I recognise the who does she think she is comment, which is typical of a small village in Central Scotland and probably all over the world. The small community is much more restrictive than urban areas. Everyone is expected to be the same, although once change eg dress choice is established people then kind of expect it. Be yourself, don’t compromise yourself to stop others judging you.

  13. I agree wholeheartedly with you on this. It’s good to know that I’m not the only one who often has a crisis of confidence over what I wear, particularly on the blog. Just this lunchtime my husband laughed as we walked out of the office, me in my faux fur coat and big sunglasses. When I asked why he was laughing he said “You look like a film star in that”. My immediate response was to ask if I looked silly, but then I thought “what the hell!” I’d rather be laughed at for looking a bit different than laughed at for looking the same as everyone else. I love to see people who dress to express their personalities. When I was younger I was terrified of standing out but now I realise that you shouldn’t let other people’s eyes become the bars on your cage. You’re right, life is short. Wear the dress, the shoes, the faux fur coat AND the big sunglasses and hold your head high!

    Emma xxx

  14. I started a second Instagram account where I could post all the fashion, food and interiors that I love without feeling like I had to justify my style or purchases to family or friends. I was mortified when a couple of people I know in real life started following it. Then I thought “No, this makes you happy. If they weren’t interested they wouldn’t be here.”. We can’t let our joys be dictated by others.

  15. I used to stare longingly at all the clothes that I wanted to wear but felt too insecure to. When I did start wearing the things I had always loved guess what happened? I no longer felt insecure because I was finally feeling like my outer appareance matched my inner one. It was amazing – in fact, it still baffles me. So these days? I wear whatever I like, size 20 or not.

  16. Thank you! I needed to read this. For all the times i heard my skirt was too small, my dress too girly and my outfit too colorful and felt inadequate instead of fabulous. Life is indeed short and i wont have these tonned legs forever so i might as well wear the mini skirt while i can ?

  17. Thank you! I needed to read this. For all the times i heard my skirt was too small, my dress too girly and my outfit too colorful and felt inadequate instead of fabulous. Life is indeed short and i wont have these tonned legs forever so i might as well wear the mini skirt while i can ?

  18. I agree, you shouldn’t spend so much time worrying about what other people think of you, but they shouldn’t be so worried about what others think of them. Most people think they have to wear what’s trendy, and that if they look even a tiny bit different their life is over. I honestly don’t care about trends even in the slightest: I’ll wear whatever I personally like, and it doesn’t matter to me if it doesn’t look good on me, fit the latest trends or if others don’t like. All that matters to me is that they’re clothes that I like, which is usually sneakers, either normal, high waist or ripped jeans and a shirt. When it comes to the shirt, I’m sometimes told by friends that it looks childish because it has a cartoon character on it, but at this point I’ve learned to say “fuck it” and not care.

  19. I know this is a super old post, but I wanted to let you know that I have it bookmarked, just to remind myself to wear the damn dress xx

    • um, actually this was posted in 2016…which feels like a decade ago? sorry for the “super old” comment, i clearly need another coffee (and a new dress. that will help)

  20. Great article. I love wearing mohair sweaters, but a very self-conscious as a man of doing so. I’m getting better – I’m realising that no one really notices the sweater on the whole – but this article has helped give me the courage just to wear them and, even if people do notice and think it’s weird, just to ignore them.

  21. okay lol im reading this in 2020- but i bought super cute cargo pants, and i made them an outfit with a black necktop, w a zipper.. it looks rly fun and im in luv w it but im just too scared to wear it to school tomorrow, im scared of people´s opinions.. someone, help me feel more confident .-.


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