Lean Wardrobe: Packing for a five-day jaunt to Hawaii

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.

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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.