How to Dress Up…without feeling looked down on

Wondering how to dress up to your heart’s desire, without having to answer endless questions about where you’re going, and whether you have a job interview? Here at The Fashion Police we’ve talked about how dressing up is not a crime of fashion (despite what some people would have you believe), and we’ve also talked about HOW to dress up, if you want/need to. But what about those of you who’d like to smarten up your look, but who are too afraid to ditch the jeans and sweaters because you know you’ll be looked down upon, or even just stared at, by people who consider a simple cotton sun-dress to be the most outrageously over-dressed item in existence? How do you start dressing up without feeling like you’re being looked down on?

how to dress up without feeling like everyone's looking down on you

How to Dress Up… Without feeling looked-down on

In an ideal world, everyone would be able to dress exactly how they want. Those of us who like to wear dresses and heels would do so, and no one would think anything of it. Those of you who like to wear your pyjamas in public, meanwhile, would be free to do that too. There would be no tiresome questions to answer, no smart remarks, no…well, there would be no US, now we come to think of it. Gulp.

This isn’t an ideal world, though, and if you’re someone who loves to dress up, you’ve probably had at least one or two negative reactions to that, whether it be people asking how you can be “bothered” to get “all dressed up” every day (as if pulling on a dress is SO MUCH HARDER than pulling on a pair of jeans…), all the way to comments designed to make you feel silly and vain for making an effort with your appearance.  How do you get past this? How do you stay true to your style without feeling self-conscious every time you step out of the door? Here are our tips on how to dress up, in a world in which jeans are seen as the  ideal outfit for just about everything…

How to dress up when you’re used to dressing casually

If you’ve spent your entire life dressing very casually, suddenly turning up to work wearing a prom dress, complete with petticoat, heels and a full-face of make-up WILL cause a bit of a stir, and you WILL spend the entire day telling people that no, you’re not going “somewhere special” later, and you don’t have a job interview… and then maybe another day or two dealing with the inevitable “But how can you be bothered?” and “I’d NEVER have time to dress like that every day!” comments. There are two possible approaches you can take here, and which one you choose will depend on your personality, and how you feel about being the centre of attention, albeit temporarily.

1. Softly-softly

If you really dread the thought of people making a big deal about your new look, one way to combat this is to introduce the changes gradually. So, rather than the scenario above, where you leave work (or college, or insert-your-situation-here) at night dressed in jeans and a sweater, and arrive the next morning looking like Dita Von Teese, you start off with a few accessories, say. Or a bit of makeup. Or a new hairstyle. (Actually, hair is a good distraction technique, because people will notice that you look different, but will assume it’s all because of the new hair, rather than a whole new look.) Try a skirt with that sweater rather than jeans. Gradually make changes until you arrive at your chosen look: we can’t promise no one will ever notice, but at least it’ll be less of a big deal than making all of the changes at the same time. Our post on how to dress down an outfit will give you some more specific tips on how to take a “dressy” outfit and turn it into something less likely to attract comment.

2. Brazen it out

The fact is that although people will obviously want to comment on and talk about a dramatic change in appearance, they won’t be able to talk about it forever. If you’re able to just steel yourself for a couple of day’s worth of comments and questions (When you’re asked why you’re dressed “like that”, just tell the truth: that you’re trying out a new look), you’ll get it out of the way, and pretty soon people will find something else to talk about. After a while you’ll no longer be an object of interest: you’ll simply be The Girl Who Dresses Up All the Time – and there’s no shame in that.

woman playing dress-up

This probably ISN’T a good example of how to dress up without people looking down on you…

Understand that what other people think of your outfits is none of your business

There is absolutely nothing wrong with enjoying fashion, or having your own style. We can’t say this often enough, but taking pleasure in a pretty dress or great pair of shoes does not make you shallow or vain, and it doesn’t mean you can’t ALSO take an interest in other things in life. Unfortunately, however, our choice of clothing does tend to define us in a way that other hobbies and interests don’t: no one would assume that people who watch a lot of TV must be vapid, for instance, but they WILL make that assumption about someone whose hobby is associated with their own appearance. Really, the only way to make your peace with this is to understand that your clothing doesn’t define you any more than your favourite TV show does… and also to understand that you may never be able to convince other people of this. They will think what they want, and you will wear what you want: once you’ve accepted that, you can get  on with your life without giving it another thought.

Realise that people care less about your what you’re wearing than you think they do

If you dress differently from “the norm” in ANY way, people will notice. They will stare. They might make some kind of comment, or ask you a question about your chosen look. Once they’ve done this, though, they will move on, and you should too. That person who stared at you so rudely on the morning commute probably forgot all about you once you were out of their line of sight. The co-worker who asked why you were “all dressed up” didn’t spend the entire day obsessing over your outfit. The man in the lift who asked how on earth you can walk in those shoes isn’t still thinking about it, and even if he was – even if ALL of them were – would it really matter? 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 notice 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 fact 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.

Not all attention is negative attention

Another point related to the above is the fact that not everyone who stares at you, or makes a comment, is doing it because they’re looking down on you, or thinking something negative. For all you know, they could actually be admiring your outfit – or wishing they had the courage to wear what THEY want every day.

Life is too short not to wear what you want

Ultimately, the most important tip on how to dress up isn’t a “how”, it’s a “why”. Or rather, it’s a “why not?” When you’re lying on your death bed, after all, you’re not going to regret wearing beautiful clothes while you had the chance. You may well regret NOT doing it, though: why take that chance?

© Nejron | Dreamstime Stock Photos & Stock Free Images


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