Packing Tips from a Recovering Overpacker

Now don’t let the term “recovering overpacker” fool you. I haven’t become a minimalist who’s here to tell you how to fit your life into a carry-on. Instead, I want to offer some real talk about what it means to pack in a way that works for you. Because that’s what I’m all about: customizing travel experiences, and helping you figure out what works for you. 

If you’ve ever stressed over what to bring, started lists months in advance, or second-guessed your suitcase strategy, I’m here to offer some personal advice.

First Things First: You’re Not Packing Wrong

Here’s the truth: I used to beat myself up over how hard packing felt. I’d spend weeks scrolling blogs, watching YouTube packing tutorials, and searching for that one magical tip that would turn me into the type of traveler who floats through the airport with a featherlight bag.

Spoiler alert: that never happened.

What did happen is that I finally realized my packing anxiety wasn’t about not knowing how to pack. It was about thinking I should pack like someone else.

And that’s where it clicked for me: there is no one-size-fits-all packing method because it’s based on your travel style, who you’re traveling with, and what you’re doing. Your approach to packing is really a bunch of packing strategies in one. What works for a minimalist backpacker in Bali isn’t going to work for someone traveling to the mountains with a four year old (hi, that’s me), or for that girls’ trip to Scotland. 

Packing should be based on your priorities, your comfort level, and your style. Period.

(Also, I created my company, Wild Hair Travels, to help women figure out exactly what they want from a vacation and then deliver a one-of-a-kind experience tailor-made to their unique travel styles. So of course my advice for packing is going to follow the same philosophy.)

My No-Shame, Works-for-Me Packing Strategy

So this is me: I like to feel prepared. I don’t want to waste precious vacation time hunting down sunscreen, Tums, or a bathing suit because I was trying to save space. I like having outfit options, layering pieces, and the right shoes for the right activities. I like looking cute in my photos and not repeating the same outfit every day. 

Is that extra? Maybe. 

Do I care? Not anymore.

The key is knowing what makes me feel good while traveling—and building my packing strategy around that.

So here’s a peek at how I pack. This isn’t the gospel of packing—this is just what works for me. 

My hope is that you will find a tip or two that will make your next trip easier or give you a few ideas of how to approach packing in a way that is meaningful to you.

Love podcasts? You can listen to my take on packing on episode 96 of the Happy Women Travel More Podcast!

1. I almost always pay to check my luggage

I don’t care if there are extra fees to check luggage because I don’t want to deal with my suitcase when I’m in transit. I’ve also (knock on wood) never had my checked luggage lost in almost 20-years of traveling, so while that possibility always crosses my mind, I don’t have a strong enough worry to make me fit everything into a carry-on. Because of this, I typically travel with a medium-sized suitcase that has room to pack everything I might want.

Instead of lugging a carry-on roller suitcase through the airport, I carry a backpack and a small crossbody fanny pack for my wallet, some key essential clothing, and necessities. Hands free, stress free.

2. I pack the “what-ifs”

I know myself: I will feel better if I have those items on-hand that I might need rather than having to search for them in a foreign destination when the need arises. I am simply not someone who says “don’t worry, you can buy it when you’re there”— believe me, this girl is gonna worry. And be annoyed at wasting vacation time hunting an item down that I could have slipped into my suitcase.

My carry-on backpack is sure to have some key clothing essentials in case my checked bag gets delayed. For a beach trip, that might be a swimsuit and change of clothes; for the mountains, my mid-layer sweater and maybe even hiking boots. I also include meds like Tums or Gas-X (TMI, but it matters!) so I’m not miserable mid-flight or stranded in the middle of nowhere looking for a pharmacy. And of course I pack snacks and an empty water bottle.

3. I roll my clothes

Years ago, I did get one valuable packing strategy from someone that has stuck with me: it saves space to roll your clothing. I roll every single item, even my underwear. And added bonus of rolling: it helps keep my clothes less wrinkled. 

I place my rolled clothing into zippered packing cubes. Dirty clothes get rolled and put in space-saver bags so they’re contained and not intermingling with clean stuff.

4. I plan outfits by day, activity, and photo ops

The number one way that I’ve been able to simplify packing is to plan outfits and utilize a capsule wardrobe-esque strategy. Doing this simply results in less clothes (most of the time) because you are being more intentional.

For example, if you’re visiting a beach destination, your outfit combinations are pretty simple—think breezy dresses, a few swimsuits, a cover-up, cute tanks, shorts, and sandals that can pull double duty from poolside to dinner. Accessories like a wide-brimmed hat or statement earrings go a long way in making your limited wardrobe feel fresh in photos without taking up much space.

If you’re visiting a chilly destination, embracing the layering game is key. I focus on packing a few high-quality base layers, a couple of cute mid-layers that work both day and night, and one outerwear piece that looks good with everything. A neutral coat or jacket, a mix of textures, and a cozy scarf can make it feel like you’re rotating more outfits than you really are.

When you plan outfits by activity and vibe (rather than packing 15 “just in case” options), you free up space and save yourself the daily decision fatigue of “what should I wear today?”

5. I bring (no more than) three pairs of shoes

I didn’t make this up, but I usually follow the “three-shoe-rule” when I travel. My three pairs of shoes can vary by destination and the season I’m traveling in, but these usually include:

• Boots. My favorites are: Blundstone chelsea boots, Columbia hiking boots, and Oboz hiking boots.
  
• Everyday comfy walking shoes, like a lifestyle tennis shoe. I’m loving my Toms no-lace tennis shoes lately.
  
• Activity-specific: either a dressy option, or another practical shoe based on the activities I’m planning to do, like my Teva hiking sandals.
  

6. I choose the right bags 

All said, I want to pack items that make me feel put together and prepared, and one of the best ways I’ve found to do that is by choosing the right bags. When I was traveling with my 15-month-old son on his first trip, my drawstring-top backpack, doubled as a diaper bag and purse. Plus it’s cute, practical, and easy to access everything quickly. 

Another fantastic item is the cooler backpack my husband carries (which we use the heck out of on nature trips).

Maybe You’re a Thoughtful Packer

The biggest shift for me has been giving myself permission to pack in a way that feels good and fits my needs as a traveler, not some minimalist mold I think I should emulate.

And that’s the mindset I want to offer you as well. If you’re an overpacker, or just a thoughtful packer (let’s rebrand it, shall we?), I see you. 

Stop making yourself wrong for wanting to feel prepared. Embrace your travel style. Take the tips that help, toss the ones that don’t, and know that your way is just right for you.