There’s a dress in my wardrobe that every now and then I pull out, look at wistfully for a few minutes and then put back carefully.

It’s a strappy black dress that I bought in a posh shop in Italy when I was 16.

At the time I loved it so much because it was the first ‘grown up’ dress I owned. I adored it for so long because it could be worn smart or casually and it was also great for hiding the rolls of flab I had acquired year on year.

It came to university with me, I wore it to parties and up until last year, I was still wearing it quite regularly.

But for some reason, as I edge ever closer to 30, I can’t help feeling a little bit uneasy about cavorting round in a dress I wore as a teenager.

Obviously I’m not old by any means, but it’s almost like there’s come a point where I shouldn’t wear it anymore, and I can’t quite put my finger on why.

Which leads me to ponder the question – at what age should women start dressing age appropriately and should they even do so at all?

Let’s look at Madonna. She turns 56 this year but dresses not dissimilarly to her 17-year-old daughter Lourdes. Because of this, she gets a lot of grief for her choice of attire, which in recent weeks has included a leather corset thong and mini skirt.

I bet there are many middle-aged women out there thrilled that Madonna is able to carry it off, and see her as absolutely empowering.

But I’m sure there are also others that would prefer to see the pop icon wrapped up in a smock or woolly cardigan every time she makes a public appearance.

And let’s not forget Cher back in 1989, who seemed to start it all off when she wore little more than a single leather strap and fishnet tights to star in her video If I Could Turn Back Time.

In her mid 40s at the time, she raised many an eyebrow when she cavorted up and down a ship next to her teenage son.

Have Cher and Madonna gone too far? In fairness, it is part of their jobs to push the boundaries. They both have the figures for it and no rolls of fat in sight, so some might say why shouldn’t they?

It doesn’t mean women of their age should start rolling up to their office jobs in leather mini-dresses, but does age really matter if you look and feel good in a certain outfit?

It’s 2014 – have we evolved enough now so that if women want to go a bit wild every now and then they can, or is dressing conservatively the only way we women will be taken seriously in today’s day and age?

Perhaps I should ignore my inner uneasiness and keep wearing that black dress for as long as I think it’s fashionable.

I am interested to hear what people think about this, so let us know your views by tweeting @Chester Chron.