As I write this, I’m preparing for a trip to Hawaii. While there, I’ll be in a few different social situations (as opposed to just plopping down on the beach the whole week).

Here’s the thing. We’ve talked about a Lean Wardrobe before, and preparing for a trip is one of the best times to put it into practice.

For one, I never check in my luggage, unless I’ll be gone for more than a week. I always bring one carry-on (usually a large duffle, but this time, actual carry-on luggage) and a backpack. Having one carry-on forces you to pack very strategically and with the Lean Wardrobe principles in mind.

Like I mentioned, I won’t just be lounging around all week. K and I are finalizing plans for our wedding, and we’ll be talking with vendors, participating in food tastings and cake tastings, and other random meetings where clothing isn’t exactly optional.

I also plan on going to a few nice dinners and hopefully check out some rad shops while I’m in town.

Below is my humble haul, in case you were curious

One dress shirt, one sport shirt, two polo shirts, two T-shirts, two pairs of trunks, a pair of workout shorts (not pictured), two pairs of linen / cotton shorts, washed red chinos, a blue / white stripe cotton sport coat, a straw trilby, some socks, and one belt.

I’ll have four pairs of shoes: the dub monks for when I’m out in nice places, the grey suede driving shoes for the more casual afternoons / evenings, the beat-up Converses for gym time, and the flip flops for the beach (pretty much the only time they’re acceptable).

From top to bottom, left to right:

Light blue dress shirt – Fifth&Brannan
Light gray gingham sport shirt – J.Crew (others)
Seafoam green polo – J.Crew
Pink polo – Polo Ralph Lauren
T-shirts – Target
Brown trunks – H&M (similar)
Blue trunks – J.Crew (similar)
Linen shorts – Old Navy (similar)
Washed red chinos – Dockers Alpha Khaki
Sport coat – Macy’s / INC (similar 1, similar 2)
Trilby – Urban Outfitters (similar)
Reusable bag (underneath trilby) – Baggu (similar)
Socks – Pact, Lorenzo Uomo (similar)

Shoes, left to right:

Dub monks – Antonio Maurizi (others)
Grey suede driving shoes – Banana Republic (similar)
White canvas shoes – Converse
Flip Flops – Old Navy

How to pack, Lean Wardrobe style

Give yourself options, just not too many

Are you REALLY going to need five button-down shirts for a weekend trip? Will you be using four different belts? You won’t actually use all the clothing you bring. Just be honest with yourself, and take only what you need and will use.

Sit there and analyze it if you must. Picture yourself wearing your clothing. Are you going to wear that pair of dark denim while you’re in 80-degree weather? (I asked myself that, and I decided no.)

Lay it all out, and start minimizing your haul one piece at a time. For example, I may not bring those red chinos, because I’ll be wearing my Bonobos chinos on the plane, along with another sport shirt and that sport coat in the photo. I’ll also be wearing that belt. The less you bring, the better.

Everything should pair nicely together

The whole key to having a lean wardrobe is owning pieces that all place nicely with each other. Same idea when you’re packing for a trip. It’s like a mini, curated version of your lean wardrobe.

Everything I’m bringing works well together, which makes mixing and matching things a breeze.

For example, if I’m heading to one of the meetings, I’d choose from some of my dressier options. So I can wear the brown chinos (not pictured) or the red chinos. I can wear the light blue dress shirt or the light gray gingham. I can wear the dub monks or the grey suede driving shoes.

At the same time, if it’s a more casual meet-up, I can wear one of the linen shorts with any of the shirts I brought. Or, I could wear the brown chinos with either of those polo shirts. I probably wouldn’t wear the red pants with the hot pink polo, but possibly with the seafoam green one.

Bring clothes that all pair nicely with each other, and you’ll have a much easier time.

Don’t forget the little things

Dopp kit? Shaving stuff? Hair product? What about underwear, socks, T-shirts? Sunglasses? Chargers for your electronics?

By the way, the “little things” add up, so only take what you need. Being lean works wonders in all aspects of your life, but especially when packing for a trip.

Hope these little helps the next time you find yourself heading to far-flung locales!

Over to you

What are your best packing tips and techniques? Do you often pack more than you need, or are you pretty good at minimizing your haul? Let’s hear it below.

If you found this article useful, make sure to check out our Lean Wardrobe resources page.


24 Responses

  1. Paul David Olson on

    I do a quick post-trip review of what I didn’t wear or only wore once and purge that stuff from the next trip. I found Hawaii to be incredibly casual — especially with footwear. You may want to consider leaving the monks at home. Those drivers are great.

    • Barron on

      Yeah, this is a good idea. I’ll do a follow-up post of some sort. The monks have gotten some use (I had a few more formal engagements to attend), though I’m sure the drivers could’ve subbed just fine. It’s difficult knowing exactly what won’t see much use and what you could’ve brought more of, until you’re actually on the trip 🙂

  2. Rob Stephenson on

    I’ve always found it so much easier to pack for the tropics or at least warm destinations. You may want to consider a travel umbrella or similar for those sudden downpours that tropical locations do so well, and consider whether the trunks would serve double purpose as workout shorts. (I’d save the trunk space with speedo-style swimwear, but that’s a personal decision that varies between individuals).
    Where I struggle with packing is heading into a deep winter destination with snow etc – the need for coats, gloves, layers of clothing including thermals is daunting, particularly if the trip also has a business focus where one needs to be suitably presentable, as well as dressing more for comfort on other days.

    • Barron on

      Good call on the travel umbrella. It actually has rained while I’ve been here and we had to buy one (we brought a faulty, broken umbrella, ha!)

      Traveling lean to a wintry destination IS difficult. There are just too many factors, although, the topmost layers can easily be reused (sweaters, coat), while the base layers (shirts, thinner layers, etc) can be changed more frequently. It’s inevitable that more clothes are needed in more chilly destinations.

  3. Patrick on

    Great timing! I’m getting ready for a trip to Maui this week and needed some inspiration for what to pack. Normally I do a decent job of minimizing what I bring, but there always seems to be at least a few items that don’t get worn.

    What are your thoughts on packing technique? Fold or roll?

    • Barron on

      I’ve tried both. I’m partial to folding simply because I’m used to it. I fold minimally so the clothes aren’t as tall, so more fit in the bag.

      And yes! There are always items that go unworn; I think it’s unavoidable. There are also items I wish I brought more of. Every trip is different, so it’s not always easy to pack minimally and effectively.

      Have fun in Maui!

  4. Merozo Baro on

    Forgot to list the most important: What carry-on luggage you are using 😉 j/k

    Do you bring shoe trees when traveling?
    Any upgrade on storing footwear (well those that don’t come with bags) that isn’t a store plastic bag?

  5. Dude on

    You haven’t been to Hawaii before have you…this wardrobe is too over dressed and still too many items for the islands. Good luck. Let us know how it goes.

    • Barron on

      Been quite a number of times. Like I mentioned in the article, I have a few “dressy” engagements to attend (instead of just lounging on the beach), thus the blazer + dress shirt options. I’ll do a follow-up post to detail what I used vs. what I could’ve left at home, etc.

  6. Gordey Natalenko on

    Lean? I have to disagree. Four pairs of shoes for a 5 day trip is overkill. 6 shirts? That’s ridiculous.

    I would wear a linen shirt, casual pants, and loafers onto the plane and just bring one pair of flip flops, swim trunks, one Tee, one shorts plus underwear.

    • Barron on

      I’ll do a follow-up post to detail what I actually used, what I should’ve brought more of, what could’ve stayed home, etc.

      • Gordey Natalenko on

        Sweet, I’m curious. Then again some guys are clothes whores 😉 So I could understand. Or maybe there are lots of activities you did. Then it also makes sense.

        I would just plan on chilling on the the beach and maybe a restaurant and bar, so I wouldn’t take much.

  7. Ka'imi on

    Great post. I’m assuming you’re coming to Honolulu, so you might also want to check out Aloha Rag, 88 Tees and Kicks/HI if they aren’t on your list already. Been a bit rainy these past few days but hopefully it’ll clear up by the time you arrive! Ke aloha nō!

    • Barron on

      Appreciate the suggestions. I’ve been to some of the spots you mentioned. It rained a little bit when I was there, but no big deal 🙂 Thanks for reading!

  8. Michelle on

    Great article. I like that you incorporated brighter colors – it really gives off a tropical vibe.

  9. Qntn on

    Wow some of you guys are a little harsh! If it fits in a carry-on, it’s lean in my book. Besides the objective is to be light and versatile, not self deprivation.

    I would just add, if you’re going for a longer trip, be sure and pack some of those laundry detergent capsules (e.g., Tide Pods). They are super handy for hotel laundromats. If you can wash once or twice, you can keep your packing lean.