I have just got back from short hol in Santorini and had lots of compliments about looking "so glamorous" mainly due to my new wide/floppy brimmed straw hat. Not actually straw but one of those you can roll up to put in your luggage. Was only £20 from amazon. To be honest I usually look a bit of a hot mess on holiday and don't care too much but I got The Hat because I sometimes now have to wear glasses for distance and I wanted something to keep the sun out of my eyes if I swapped from sunnies to specs. Even my husband who isn't a very noticing person said I looked like Audrey Hepburn in my big hat and big sunglasses!
I do have semi permanent eyebrows and get lashes put on for holidays so I it doesn't matter how much I swim. I have quite greasy skin and use a mattifying facial sunscreen from la roche posay (F50) which helps a lot. I do wear a bit of foundation over the top, waterproof eyeliner and lip gloss.
Clothes - I try to keep it capsule style, mostly black, some white and a bit of blue this time (in honour of Greece!), so everything mixes and matches. Even my bikinis are black or white and can be worn as underwear during the day so I'm always ready to whip off the outer clothes for a swim. Nothing that needs ironing. Shorts and camis for the day (have some fab shorts from Halara that look like a short skirt but are actually "modesty shorts" with a floater layer over the top) and maxi dresses for the evening. Also a plain black swishy poncho for chilly evenings and the plane. Looks very elegant with The Hat too!
No patterns or minimal patterns. These can look nice but I never get it right and they look garish on me. Even my sarong is plain black with a little gold coin pattern on the edge. My daughter kept nicking it (and my hat and sunglasses) to pretend to "walk the runway".
Sparkly flip flops for the pool/ beach and black Geox platform sandals for walking. So comfy, even climbed the volcano in them.
Small cross body bag for valuables. (Really need to replace the one I've got as looking a bit tatty!) Fold out Longchamps bag for bigger stuff (water, sun lotion etc) - was given this for my birthday recently and I love it so much. Much more stylish than a duffel bag or rucksack, waterproof for any spills and folds up tiny to go in main luggage when not using.
Sorry to bang on but I actually felt like I got it right for a change and it was so nice!