Smart Packing Tips You’ll Actually Follow

I haven’t checked luggage since my first trip to Paris in 2011. I’m not sure how or why my obsession with carry-on traveling began, but it’s become a strict policy of mine. There’s something really satisfying about getting off a flight, luggage in hand, strolling past baggage claim, knowing I’ll be at my destination well before my former checked-bag self would have even left the airport. It feels like I cracked a life code and beat the system. A tight luggage edit means there’s less to think about and more time to enjoy vacation.

So, how do you crack the code?

Rule #1

Don’t bring anything you don’t normally wear. On my vacation to Greece I ended up schlepping around a “going out” dress I thought I’d finally break out and a pair of heels I haven’t worn in years. If you haven’t worn it in the last year, I can almost guarantee you won’t wear it on vacation.

Rule #2

Don’t underestimate the power of versatility. This brings me to seven items I’ve found help me beat the packing game.

1. A sarong

J.Crew shirt, vintage scarf as sarongJ.Crew shirt, vintage scarf as sarong

Does anyone else think it’s kind of rude that sarongs have been pigeonholed as a beach-only article of clothing? They have so much sartorial potential! I wore one as a bandeau with high-waist cargo pants and the other as a skirt. I also styled it over a T-shirt one night for dinner. Even so, you only need one.

2. A calf- or maxi-length dress (preferably one with buttons down the front or a low back)

I know this one’s pretty specific, but I promise it’s worth your while. I packed this Sleeper one and an old Ulla Johnson one I snagged at a sample sale. It’s no coincidence both of these have buttons all the way down. Buttons = infinite possibilities. You can wear them the “normal” way, completely open as a cover-up, or buttoned half way up the sleeves tied around your waist to create a skirt. (Styling hacks 1 and 3 also work with a dress that has a low back.)

Now it’s time to meet my beloved friend. He’s kind of an annoying one-upper, but in all honesty, he’s the true hero piece here:

3. The button-down

You can wear it normally, open, tied as a crop top, off the shoulder, backwards and tied with your back exposed. If it’s oversized, you can make it into a skirt. That’s six different ways (!) to wear a button-down right there. I packed two for this trip but you can definitely get away with one for a long weekend. Man, I friggin’ love button-downs.

4. A pair of shorts that aren’t denim

These from Derek Lam 10 Crosby have been one of my greatest purchases. They make denim look lame and are refined enough to wear to dinner with — you guessed it — your button-down.

5. Wide-leg trousers (perfect if you hate shorts or just need another bottom option)

Ganni belt as bandeau. Zara pants -- similar here, vintage beltGanni belt as bandeau. Zara pants -- similar here, vintage belt

I love the contrast of roomy cargo pants with a bathing suit or a crop top (read: sarong). I think it looks really cool and unexpected and kind of makes me feel like Kim Possible, which is pretty neat. They also get brownie points for being comfortable enough to travel in.

6. Shoes

Because you’re unfortunately going to have to wear shoes at some point, go with a foolproof sandal and a pair of closed-toe shoes.

You know when you get something new and you wear it so much that you don’t know how you ever lived without it? These ATP Atelier sandals have been exactly that for me. They’re simple yet elegant and therefore perfect anytime, anywhere. If you’re one of those people who likes a little bit of height, there’s no better way than Castañer’s espadrille wedges.

A pair of closed-toe shoes are good for a spontaneous hike, the airport, and essentially anywhere you don’t want your toes to be exposed. I’d go for an oxford, a loafer or a sneaker.

7. A bathing suit to swim in, rinse, repeat

Before leaving, my best friend and I were concerned that we didn’t have enough bathing suits for a full week of beaching. To our surprise, more than half of our suits went untouched. She wore this Matteau one-piece the entire time and I wore this Her the Label one quite a bit. You can get away with bringing one for every day since they take up so little space, but I say pack two bikinis (I can’t stay away from high waist ones right now) and a one-piece in the name of a tight edit.

The Icing: Accessories! Accessories are the easiest and least spacious way to change up your lewk. I packed a bunch of Roxanne Assoulin bracelets, Gimaguas necklaces and two different colors of these Topshop sunglasses.

Add in underwear (plus a few extra pairs), any necessary boob support and toiletries (employ the same mindset here as you did with clothes and consider what you actually use each day), and then…

Ta-da! I bet your carry-on is not even full right now, which brings me to my third and final rule.

Rule #3

Don’t pack things just because you have room. I don’t know why, but I always do this. I think, “Hey! I have so much extra room! Let me bring a bunch of useless things I won’t even look at it!” It’s a recipe for regret.

So, tell me. How’d you do? Are you dancing your way to your gate at this very moment?

Photos provided by Juliana Salazar. 

Juliana Salazar

Juliana Salazar is a freelance stylist and brand strategist and contributing fashion editor for Man Repeller.

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