When packing for a mid-winter holiday, be it beach or snow, I have one rule of thumb: less is more. In a previous job/life I had the enviable privilege (or doomed fate) of boarding a plane once a week for work. I learned to trim the art of packing down to the bare essentials: a great sports jacket, a dark pair of jeans, a few crisp white shirts, one pair of formal shoes and one pair of trainers. The less I needed to lug around the better. I fit everything into a wheelie carry-on and got out of airports in no time at all, without having to wait around the dreaded baggage carousel.
These days, with my personal travel sadly much more infrequent, I now tend to check luggage in. Not being in a rush, I prefer to bring liquids, which of course you can't carry on. I find it hard to rely on hotel amenities these days - most hotel private-brand shampoos are like paint stripper. It's also nice to be able to bring along more clothing options, as you never know what situations may arise while on holiday!
When it comes to carry-on, a Louis Vuitton Pegase in charcoal Taiga leather is probably the chic-est "wheelie" out there. For hard-sided check-in luggage I love what Rimowa are doing. You can also use them as an in-room safe when travelling, they're so indestructible.
What to pack is subjective but there are a few good rules of thumb:
Shorts for sunbathing (Orlebar Brown is a great choice).Speedos are acceptable only if you look like David Gandy or an Olympic diver.
Please keep shorts above the knee; it makes for a better silhouette and allows those more portly (read moi) to look less so.
Jandals or sandals? Jandals, and preferably Havaianas. Few men can carry off a leather sandal with aplomb, unless they're from Positano.
Please also avoid polo shirts with huge logos or country-club decals - we don't need to know where you golf back home. And for evening, please leave wife-beaters and surf shorts back at the villa. The ladies always get dressed, so it's time to try doing so as well.
When on the slopes, colour is good, but limit it to two to three colours at a maximum.
Avoid all black, it just looks boring. Those who try to look cool in jeans just look foolish, as do those not wearing helmets.
For apres ski, Moncler is increasingly the choice of the Euro(trash) set, but it does make gorgeous stuff.