How to have the confidence to wear whatever you want

“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.

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 going 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.

Related: How to walk in high heels for beginners