Along with these skills, I am also an obsessive list maker. So, over the years I have learned to make lists when it comes to packing. I break my trip into days and plan out an outfit for each day and each night. This is easier when I know what I have planned, but sometimes I just have to wing it, in which case I pack something that is more versatile (i.e it will work for dinner or a night out w my girlfriends, etc). I try to overlap things such as shoes, pants, and outerwear, but I really dislike having to re-wear things like tops or dresses. If I wouldn't do it at home, why do it on vacation? With that said, I do have some standard outfit formulas that I use when packing, regardless of the season or the occasion.
A family/nice dinner: on pretty much any trip, I end up having a nice dinner with family or friends. This is especially true for the holidays. I typically like to pack a nice top (usually bedazzled or a fun print) to match with a pair of skinnies. The skinnies can then get recycled throughout the trip. When it comes to shoes, the longer the trip the less likely I am to pack heels. I rarely wear heels during the day, so flats are more versatile and a better use of space in my luggage.
Casual day outfits: I usually need lots of these that can easily translate from walking the dogs with my mom to shopping to getting coffee with friends. So, I pack a couple of tops that will go with a cardigan or a blazer, and then a pair or two of skinny jeans. This way, the cardigan, blazer, and skinnies can be swapped around with different shirts.
Girls night out: cute outfits to wear out with my friends when we go to dinner or bar hopping is also definitely important. A skirt or cute pair of leggings, along with a fun top with evening appropriate details (ie a fun neckline or other embellishments). Fun flats or booties help complete the look. However, I again like to stick to flats because I can easily rotate them through my outfits, and they are easier to pack!
Packing always makes it harder to plan outfits, because you have to pick and choose things, and you never know what the weather or changing plans will have in store for you. But, by packing at least something for every occasion, you can always be prepared.
Until next time,