How To: Plan Outfits for Travel

I love planning outfits for trips. I mean, I love the act of planning (thanks to my crazy OCD) but I also love planning what I'm going to wear. I love the anticipation and I love the memories tied to certain outfits after they've been worn abroad.
I've got ideas/guidelines for four different types of trips.

It can be difficult to pack for cold weather trips because cold weather clothing is so bulky and the process of being outside and then inside and back outside can be stressful for people who hate extreme temperature changes. The key is to pack layers that you can pad on to protect yourself outdoors but also peel off to accommodate indoor activities. And you don't have to pack much. I'd say three or four outfits, max; basically just whatever will fit in your bag. Honestly, if you're out sightseeing, you'll be in your coat the whole time so what you're wearing underneath won't make too much of a difference in photos anyway. To maximize the room in your suitcase, wear your bulkiest items (coat, scarf, chunky sweater) to the airport.
Here are the types of items I recommend for a cold weather trip:
  • micro down winter coat - I love mine because it's incredibly warm but at the same time, it isn't overly bulky. In fact, it's v. portable and it can be scrunched up and shoved into a tiny little drawstring packet. The portability also makes it a great coat if you're traveling from a cold place to a warmer place.
  • cozy scarf - A big blanket scarf will keep you warm while you're roaming the streets and it can be used to wrap around your shoulders while you're in a cool room.
  • boots - Stylish yet functional booties are the way to go for cold weather trips. If there's a potential for snow or ice, you want non-slip comfortable shoes.
  • convertible gloves - In this age of touch screen smart phones, convertible gloves are key.
  • shawl cardigan - Big and cozy and great for layering, a shawl cardigan looks stylish and keeps you warm.
  • jeans - A thick pair, please.
  • hat - Beanie or felt floppy, whatever your preference, wear one because you lose a lot of heat through the top of your head.
  • cozy socks - Having frozen toes is the most uncomfortable thing and if you're out and about, there isn't much you can do about it so take preventative measures and insulate those feet.
  • flannel dress - If you're going to wear dresses in cold weather, at least choose flannel.
  • warm sweater - I like a big, fluffy sweater that can be layered over a T or even over the flannel dress.
  • fleece lined leggings - They're super warm on their own or they can be layered underneath a pair of jeans for extra warmth.
  • thermal t - Wear this under the sweater or cardigan for extra warmth. It's all about the layers. And this item is what I'd pack the most of and I would re-wear the sweater and/or shawl cardigan over and over.
  • crossbody - In cold weather, I like to carry a bag that's big enough to store my gloves.
For me, packing for an active trip is all about balancing comfy exercise clothes with fashionable items that transition well from hiking to dining out. Basically, you want to pack workout clothes that also double as streetwear to maximize the room in your suitcase. I'll just pack a few single-load detergent packets and run a load of laundry if necessary. These are the types of clothes I plan on bringing to a short jaunt to DC in April. I'm going for the weekend with my friend H (who was my partner-in-crime in Toronto). We had so much fun biking together that we decided to do it again. I swear, we're going to bike all over America.

Here's what I recommend for an active trip:
  • vest - A fluffy vest is great for layering and keeps your arms nice and free to move. Plus, it's chic.
  • cap - Keep the sun off your face and then use it to keep your hair tame.
  • cotton skirt - A stretchy cotton skirt is comfortable and stylish.
  • cute sports bras - I like to wear pretty and colorful sports bras so even if they peek through my top, it's not offensive or embarrassing.
  • sneakers - Sneakers that are comfortable and nice to look at are key.
  • flats - Pack a pair of easy to wear and stylish shoes that can be worn for a night out.
  • tunic - Throw a tunic on over a pair of yoga leggings and you're good to go.
  • sweater dress - It's a dress made of sweatshirt material; it's literally work out meets streetwear.
  • camisole - A plain white camisole is versatile. Layer it under your clothes so you can peel off your outer layers when you overheat.
  • yoga leggings - Plain black leggings are great for working out and can be worn for going out.
  • shorts - A pair of colorful shorts are cute for a hike and for grabbing a coffee.
  • t-shirt - Really soft t-shirts are so perfect for active trips.
  • cropped sweatshirt - The cropped shape looks stylish but the sweatshirt fabric is great for activities.
  • thermal t - A pretty thermal t will keep you warm while looking great.
  • ankle socks - These are necessary for wearing with sneakers.
  • backpack - Roomy and functional and stylish; it doubles as a place to store trail mix and a purse.
My trips usually fall under this category. Last year, I went to France and I 100% cared about how I looked during the trip (and especially while I was in Paris). Packing for fashion conscious trips means maximizing my outfits while minimizing the number of pieces I pack by choosing mainly neutrals and/or items that can be mixed and matched easily. For example, I might wear a few different tops with the same bottoms. I might throw a cardigan over a dress and then wear the same dress again with a blazer. You get it.
Here are some guidelines for a fashion-conscious trip:
  • fun skirt - Skirts are the easiest way to jazz up a wardrobe. Different tops can be swapped out to create totally different outfits so I like to pack one fun statement skirt.
  • trousers - An easy pair of black trousers are my go-to but if you're more of a khaki person or jean person, that's fine. These pants are likely going to be mixed and matched the most during the trip.
  • crossbody - Pick a bag that goes with all of your outfits and that's functional.
  • plain skirt - A plain skirt is like the easy pair of trousers. This may be your go-to item that will be mixed and matched a ton.
  • blazer - Pack outerwear that doubles as casual wear and semi-formal wear for day-to-night. I like to go with a clean, chic blazer.
  • breton t - Stripes are a neutral in my book and breton stripes are so classic.
  • fun dress - I love to bring at least one fun dress. I usually go with one that's pretty flexible; this particular striped number is a fit-and-flare so it can be worn on its own or with a top so that it looks like a skirt.
  • little black dress - This is another versatile piece that can be dressed up or down. Wear it with a woven belt for a casual daytime look; wear it with lots of costume jewelry for a nighttime look.
  • skimmers - Cute but comfortable shoes are key for sightseeing.
  • flats - Again, super comfortable shoes that are slightly fancy and great for dining out.
  • cardigan - Add a cardigan to any outfit to change it up.
  • white t - The white t is the counterpart to the easy trousers or plain skirt. It's the top that will be used the most. It's chic but it isn't a statement piece so it can be worn over and over without being offensive.
  • colored t - I like to pack one or two colored t-shirts, usually in a neutral color like navy or black, which functions much like the white t.
The tropical trip is probably the easiest holiday to plan for. It's just a bunch of swimwear and coverups. For efficiency, the coverups should also work as something easy to throw on over a suit and be appropriate for dining out. I love packing for tropical trips because the clothes are so small that they'll fit in a teeny tiny bag.
Here are some suggestions for a tropical trip:
  • romper - Rompers are super easy to throw on and they're casual and comfortable.
  • cotton dress - An easy, thin, cotton dress won't wrinkle and will keep you cool in the heat but look chic.
  • crochet dress - Perfect for a tropical trip, easy to pack, easy to wear, and will keep you cool.
  • swimsuits - I suggest packing at least three suits because you might end up wearing two in one day (one before lunch and a new one after lunch if the first one is still wet) and the third is a good backup for wearing the next day if the other two suits are still wet.
  • caftan - I think caftans look so stylish and they can be belted for a night out look.
  • maxi dress - I love a good maxi for a beach trip. They're breezy, chic, and it's the only dress that will keep your legs warm.
  • shorts - If you have great abs, maybe you don't even need to cover up your top. Just chuck on a pair of shorts and you're good to go.
  • sandals - I like sandals that are cute and can be worn out but are also appropriate for walking on the beach or hanging by the pool (i.e. waterproof).
  • crochet bag - For beach trips, the bag needs to be weatherproof and sandproof and I think a flexible crochet bag is the way to go.
  • sun hat - (Which I forgot to include in the photograph, my bad) Protect your hair and face from the sun with a straw hat. Plus, a beachy hat is also a great way to accessorize beachy, salty, wavy hair.
If you need more packing help, my packing list suggestions and other tips post may be useful. I also recommend saving all of your clothing items on Polyvore and browsing through it like a library when you're getting ready to plan for a trip. It's much easier to rely on an app than your memory to remember what you own.

The other tip I have is to make a calendar of the days you'll be gone and write down what you'll wear each day. It takes the guesswork out of the equation and is a huge time saver. That way, when you wake up in the morning, you know what you're wearing and you can just go.

Happy planning and packing!