I feel like the first part of this post could be an exact “copy & paste” from my Packed: Chicago Picks post last July. How do vacations always manage to sneak up on me?? I’m mentally packed for months, but then the week of the trip, I panic because I’m running out of time and pack wayyyyy too much stuff. At least I’m somewhat organized! I saved my packing list and vacation check list from our cruise last year on the computer, and that decision has been a total lifesaver. Is anybody else as obsessed with lists as I am? Let me know in the comments if you want to see my check list and packing list – I’ll share them in my next post!

I’m apparently predictable when it comes to packing, because I’m still including a mix of basic pieces in my bag, with a few beach necessities:

•  an oversized tee
•  printed shorts
•  Chacos (so hipster of me)
•  a maxi dress
•  a wide-brimmed fedora

I’m not usually into BLINDINGLY BRIGHT colors, but I weirdly found myself wanting something yellow for this trip. I have this pair of printed shorts from Old Navy that I fell in love with instantly, but then brought them home and realized that I don’t really know what shirt to wear them with. When I imagined what color would look good with them, the color yellow popped into my head. I don’t even like yellow! This vacation is doing weird things to me.

We’ll be at the resort for a week and I’m still not entirely sure what we’re doing each day, so I haven’t planned every single outfit. But here’s a taste!

#1: Floral scarf. Hands down, one of my best purchases ever. The craziest thing is, I can’t even remember where it’s from! Pretty sure it’s from a boutique online.
#2: “Locals Only” tank. I just got this a couple days ago from Bliss Boutique! It just screamed ‘beach vacation,’ not to mention the fact that it’s by Comfort Colors, which makes it an automatic winner.
#3:  New sunnies. I. LOVE. THESE. I found them at TJ Maxx for like $12, and the subtle cat-eye slays me!
#4: Grey printed tee. Old Navy will always be my go-to for basic wardrobe pieces. This top is super soft and the perfect kind of oversized.
#5: Hawaiian print “Keds.” (They’re not real Keds, they’re from Target.) How great is that print?? I should have gotten two pairs, because I’m going to wear these until they fall apart.
#6: Printed shorts. Old Navy strikes again! The only printed pair of shorts I owned before these had stripes, but I looked at these and was instantly transported to Jamaica.
#7: J. Crew denim shorts. Literally the perfect denim shorts. They fit like a dream. I shouldn’t have spent so many years wasting money on cheap, flimsy denim!

Other essentials for this trip include:

— waterproof beach bag
— Chacos
— sunscreen
— Downy wrinkle release spray
— cute swimsuit cover-up
— 1 pair of heels + cute clutch + statement necklaces, in case we decide to be fancy

Packing Tips

1. Make a list and stick to it.
Realistically decide how many outfits you need, based on where you’re traveling and your length of stay. Don’t play the “Oh, but I neeeeeed six cardigans because I want options” game. Or the “What if we get stranded and end up hiking across the island?? I have to make sure we have a first aid kid, bottled water, a flare, and an emergency snowsuit” game. You don’t need it all, I promise you don’t. If you’re an overpacker, gather up everything you want to take and reduce it by at least 1/3.

2. Lay out your clothes by outfit.
This helps in several ways. First, it keeps you from overpacking because you see exactly how many outfits you’re taking. Second, it makes things easy once you’re actually on vacation because you don’t have to root through multiple stacks of clothes to put an outfit together. Less time in front of your suitcase = more time in front of the ocean.

3. Before you put anything in your suitcase, group similar things together.
This might sound repetitive, but just go with me here. You’ve already stacked your outfits together, tees/tanks on top of shorts/jeans. Gather everything else up (accessories, toiletries, extras) and keep similar items with each other. This will allow for a second round of purging, if you need it, because you have eyes on EVERYTHING you’re packing at once and can see if you have more stuff than you really need. If you pack things in groups, it also makes things easier to find in your suitcase whenever you get to the hotel.

4. Fill your bag with smaller bags.
When you have lots of little things that you don’t want to lose in a mountain of clothes, put them in smaller zippered bags. It’s way easier to find your favorite pair of earrings by grabbing the bag you packed them in, rather than rifling through a pile of swimsuits.

I’m sooooo ready to lay on that beach! Jamaica, here we come!

What tricks do you use for packing smart? I’d love to know!