En Route With…Robert Denning

Random fact – Wayferer-style sunglasses are one of the only styles that look good on me.  For real – most sunglasses make my abnormally large head look even bigger, but I can always rely on the standard style to make me look good.  Which is why I love Westward Leaning so much – it gives me countless options of my favorite style, AND gives back to charity.  I had the incredible opportunity to interview their founder, Robert Denning, on his travel habits and packing style.  The result – one of my favorite installments of En Route With…  


Robert Denning
Founder & Creative Director, Westward Leaning

I am obsessed with sneakers, and always start by picking the sneakers I want to bring. You can only fit 2-3 sneakers or high-tops in the upper section of the Hartmann roller-board I use for carry-on, so if I want to bring 3+, I have to check a larger bag. So it’s either a 2-3 sneaker trip (carry-on) or a 3+ sneaker trip (not carry on, in which case I use a large Hartmann rolling suitcase).

If it’s a 2-3 sneaker trip, I am extremely disciplined. I am very much a uniform dresser, and pack the same thing for almost every trip: grey jeans, black jeans, grey t-shirts, black t-shirts, 2-3 blazers, and a few button down shirts. I don’t mind wearing the same thing day-to-day. I have a special cosmetics bag where everything is under 300 mL, and I limit myself to an iPad and Kindle only.  If it’s a 3+ sneaker trip, I allow myself the luxury of my large Hartman suitcase, which is absolutely massive. I am the most extravagant, over-the-top, bring-everything-I-own packer in the world when I let myself check bags. The cosmetics discipline goes out the window: I bring the full-sized Clarisonic, my electric shaver (I have a separate bag just for these). I bring body moisturizer, conditioner, toner… all the things that aren’t easily available in a travel size. I think it should be illegal to not offer cosmetics in 300 mL packages, but apparently the industry disagrees. If I don’t have to go through security, I basically bring half the contents of a Sephora store in my suitcase. I don’t really pack any more clothes, but I bring my laptop, my journal, gifts for people… I’m out of control.

Ironically, if it’s a 2-3 sneaker trip, it takes me a while to pack, since I want to be organized. If it’s a 3+ sneaker trip, I just dump everything I can into the black hole that is my oversized suitcase.

If I’m traveling for work, I usually need to bring the latest collection of sunglasses with me. Since these are the most important thing for the trip, they go carry-on. I have a Bottega Venetta carry-on rolling suitcase that I use exclusively for the sunglasses. It’s perfect because it’s subtle and not too branded, so when I visit magazines and retailers and investors, our products and brand are what come through.   Regardless of whether I check or not, I always use the same bag for my hand luggage. It’s this massive black duffel from Prada that I’ve had since I was 18 (I got it as a gift when I graduated from high school). It’s kind of tacky and super beaten up, and I don’t use it for anything except air travel. But it comes on every plane trip, always. It’s like my travel companion, and I either carry it on my shoulder, or I put it on the top of my carry-on rolling suitcase. I put everything important in the zip-up interior pocket: wallet, medication (I have terrible allergies), passport, earplugs, keys. My passport is the only thing I’ve never lost, and I credit this to the interior pocket. Inside the bag, I have my Kindle and iPad, my journal, and one hard sunglasses case for the pair I wear on the plane. Other than that, it’s empty. It’s kinda ridiculous how big the bag is for how little I put in it. I thought it was the coolest bag ever when I was 18 (it was the first expensive designer thing I ever owned), and even though it’s kinda out of fashion, I’m very nostalgic about it.

I went to Italy a few weeks ago, and literally missed my flight because I got to the airport too late. I have missed multiple transatlantic flights. I am not proud of this. I once got to the airport in London for a 2:10 p.m. flight, only to be informed that was the time my flight had landed in New York. I usually do make the flight, but it’s almost always down to the wire… so running through airports is my number one source of cardio.  I am a pro at rushing through security. In San Francisco (where I live), I have something called “Clear,” which means you never have to wait in line. They scan your retina and fingerprints, and you go straight to the front of the line. You have to pay an annual fee and basically give them everything they’d need to steel your identity, but I think it’s worth it.   Unless they are literally closing the flight, I always go to the lounge and steal bottles of water for the flight, since I feel like they never give you enough water (the glasses are always so tiny!).

I actually LOVE flying. I am a total geek and love planes and route maps and everything about it. My grandparents lived next to the Boeing factory in Everett, and I remember seeing the 777 take its first flight. We all stood in a parking lot and clapped. People complain about air travel, but when you think about it, it’s such an amazing privilege to be able to fly and see the world.   Even if it’s O’Hare for the 100th time, I try to remind myself how lucky I am to have the opportunity to travel by plane.

I am one of those people who has a total routine. I used to live in the UK, and traveled to the US almost monthly, so I think I’ve perfected the in-flight process. I always sit in the window seat, and if it’s a day flight, I do everything: I eat every course of food, watch all the movies I can, memorize the airline’s route map, read SkyMall (which is the most fascinating and bizarre collection of products, like, ever!), stare out the window, watch the in-flight progress… the works. If it’s something special to flying, I do it.  If it’s a night flight, I force myself to try and sleep. I put in earplugs, put on an eye mask, put on lip balm, put my water bottle next to me, and as soon as we’ve taken off put my seat back as far as possible and tune out. I don’t eat the meal, I don’t talk to my seatmate, I sleep.

I always pack sunglasses, for sure. I have special travel cases that fit 4 pairs in a very space-efficient way, and I either bring one or two of these cases. So it’s either 5 pairs (4 in the case, plus one to wear on the flight) or 9 pairs (2 cases, plus a pair for the flight). I know this seems insane, but people are always stealing them or borrowing them and then losing them when I go on vacation. And I’m terrible about gifting them to people if I see they love them. So it’s good to be prepared. Plus, if you wear the same thing every day (like me), different sunglasses (like sneakers) offer an easy way to mix it up.

En Route Essentials Robert Denning

multiple pairs of sunglassesKindle Paperwhite
FLIGHT001 packing bagsEight Hour CreamHartmann suitcase