I recently returned from holiday (Read my reasons you should go to Menorca if you're in your 30s here) and I thought I'd help answer some of your "What the eff do you take on holiday" worries.
When you pack for holiday you can often feel overwhelmed - how on earth do you know what you'll want to wear 4 days from now, in weather you can't remember how to dress for? But you don't want to overpack (heavy luggage sucks), but you also don't want to feel like crap the whole time. I'm okay with the fact that how I choose to present myself matters, I like to feel 'right', and that requires a certain amount of stuff.
So here are some of my tips for holiday packing, if you also don't like to travel too light, and don't want to look too casual while you're away in the sun.
1. The fact that I naturally stick within one colour pallette works in my favour when I need to travel. You can see from these Menorcan lift selfies that I wear blues, blacks and leopard print! This means that more things match interchangable. I only bought two pairs of shoes, and they'd both match all outfit options.
2. I took two long tube dresses, one in black and one in leopard print as I've found I just feel really good in them. They're great for day time excursions and evenings out, and easy to wash and dry should you need to. They also provide cover from the sun, and take a minute to throw on. More time for sleeping on a sun lounger! Find something you love and take more than one!
3. I bought two pairs of crocs with me, as they're an ideal holiday shoe. They work for day, night, walking and for getting wet. They're also super duper light to carry.
4. I took 4 wigs for a weeks holiday, they're not heavy and I still like options. I do own over 20 though. So my tip is generally only allowing yourself a section of the things you usually have lots of. I take a big suitcase because I know that having my 'things' with me are important. I'll never travel small, but I do try and travel light (enough to carry my bag at least).
5. Wear as many of your regular clothes as possible. I know a holiday proves a fun reason to buy a new wardrobe, but unless you're planning on lots of sunshine getaways, this just becomes a waste of money. If you need to buy something new, be strategic. I bought one dress for this holiday, but I knew I'd wear it loads back in London too. Don't buy things in 'holiday' patterns that wouldn't fir into your normal wardrobe. It's pretty wasteful but costly too.