Rule #1 for packing for a Gentlemen’s Trip: Get a woman involved. I had my wife help me put together a few outfits. And while packing is usually the second worst part of a trip (unpacking still holds the top spot), this time it was different. She poured a glass of wine. I put on a record. And it almost felt like a date night. Rummaging through my closet, pulling things out, trying combinations, getting her take. It was fun. I’ll give you a second to grab your jaw from the floor. I said it. Packing was fun.
Unfortunately for you, my wife won’t be there to help you pack. Fortunately for you, I took notes.
Here’s what made the cut for the Agave House in Malibu.
Before I Get to What I Packed…
I have to mention what I packed everything in.
Two pieces from Sterling Pacific. A 40L carry-on and a 90L check-in case. Did I need both? Probably not, no. But remember. This was the Gentlemen’s Trip (read: splurge), and first class comes with free checked bag perks. Felt like a waste not to use them.
This was my first time traveling with these bags. And they are the best I’ve ever traveled with. Hands down.
There’s a moment when you unbox something expensive and immediately understand it. These were like that. I’m not proud of this, but there was a real masculine urge to punch one when I first got them. Just to see. Don’t. The bag will win. These handsome devils are tough.
Full aluminum shells. Cold, hard, aggressively refined in their presence. Paired with Italian full-grain leather handles that feel softer than some shoes I own. It’s that balance (brutal and refined) that makes them special.
They are expensive. No way around that. But they’re backed by a lifetime warranty and repair service. So worth it if you travel even a handful of times a year.
Plenty of luggage works. Very few make you feel something. These do.
Night One: Arrival, Reset
After a day of travel, this was less about style and more about settling in. Hot tub, dinner, firepit. I wanted comfort. Stylish comfort. But still something that feels like you’re “there.” Like you’re making yourself at home.
Day Two: Work, But Different
We worked during the day, but not in a way that required much structure. Laptop open, doors open, hot tub breaks in between. The goal here was versatility. Something that works on a call and off one.
- Nike Fleece Shorts
- Knit Short Sleeve Button-Up
- Son of a Tailor Merino Sweater
- Sabah Leather Slip-Ons
- G-SHOCK Full Metal Solar
Night Two: Private Chef, Stay In
Dinner at the house. Private chef coming up from BirdeyeLA. No reason to overdo it, but also no reason not to sharpen things. This is where one simple swap changes the whole look. Bone white pants. I’ve been pairing this color on bottom with black on top lately. Chef’s kiss.
Night Three: Nobu
This is where you lean in a bit. Not formal. It’s still Malibu (i.e., beachey). Not flashy. Just intentional. One strong piece, layered well, and slightly undone in the right places. Pro Tip: when I bought the button-up at Buck Mason, the stylist helping me out recommended a Belgian Tuck, buttoning the bottom two buttons and messily tucking it in.
Final Day: Nothing Left to Prove
By the last day, you stop trying. Or maybe you finally get it right. This is the outfit you don’t think about but still want to work. It’s why I opted for my women’s jeans (see Rule #1 in intro). Yes. My women’s jeans. On a Gentlemen’s Trip. They’re baggy and bellybutton high. Comfier than sweats. Subtly checkered for a playful at-home style. Deal with it.
Earlier in the day, I wore my Waffle Nikes with this outfit. They’re what I’ve started calling “the <$100 shoes your fashion friends will ask you about.” They’re very Bode-esque.
- Imogene + Willie Women’s High-Rise Jeans (size down 2–3 in women’s)
- Zara Denim Jacket
- Nike Waffle Sneakers (not pictured)
