Why Is It So Hard To Pack The Right Clothes To Make Me Feel Good On Holiday?

I have always wanted to go on holiday with no luggage at all and buy everything I need when I arrive at my destination.

It’s not the packing I loathe, it is the choosing what to pack that ties me up in knots.

I have been to places where the clothes I have packed are too formal, not trendy enough, too shabby, too out of fashion or even worse… just don’t fit (who knew that the little black dress you wore last year looks like a black bin bag holding a tonne of potatoes this year?).

Why do Italian women appear so effortless in their flowing linen maxi dresses, flat strappy sandals, large gold earrings and mirrored aviators propped on top of their golden heads? They create a vision of tones; bronze (their tan), beige (their dress) and khaki (their shoes), which just look so stylish, and by comparison I am as red as a beetroot, covered in heat rash – and why oh why did I pack a red swimsuit that matches my skin tone?


It’s not that I don’t try, trust me I do. I buy swimwear (well, mostly cover-ups) all year round. Money is no object in pursuit of the holiday clothing; when it all boils down to it I probably spend more on the contents of my suitcase than the holiday itself – only to unpack it all and think what a load of rubbish! That orange silk maxi dress had so much promise… but now it just looks plain ridiculous – my daughter said I looked as if I had dressed in the dark!

It never used to be like that. I once went on holiday for two weeks to Barbados and took my entire wardrobe in a carry-on. One pair of beige wedges, one pair of flip-flops, half a dozen bikinis (all mix and match), a throw and a couple of white dresses, shorts and a few T-shirts. If I packed like this now I’d never leave my room!

Now I need one bag JUST for shoes (and never wear any of them!). So what to do?

Comfort and casual are the two bywords I am putting to the forefront of my mind when I am packing this summer. I have always thought it is better to be underdressed than overdressed so I am following my own advice and I am not packing too much, as this gives too much choice when on holiday and that’s when all the problems start!

I stand in front of my wardrobe and I say – Right! What to wear for breakfast? What to wear if I go into the local town shopping? What to wear for dinner on the beach, in the hotel, at a casual bar? What is comfortable, casual and makes me feel good about myself?

Result? I end up with two things in my bag. My dressing gown and my flip-flops!