Designer Jamie Haller Says Checked Bags Are The Only Way To Fly

Carry-on luggage or checked bag? Window or aisle seat? Tropical sandy beaches or majestic mountain ranges? You can learn a lot about a person through their travel preferences and habits. TZR’s series Get Out Of Town gleans tips and habits from tastemakers to better understand what makes a first-class getaway.

As the designer of an Italian-made shoe brand, Jamie Haller spends a lot of time on the road — er, in the air. Between market appointments in New York and Paris and the regular check-ins with her manufacturers in Italy, it’s safe to say the Los Angeles-based mom of two always has her bags packed. Throw in the fact that, since launching in 2020, Haller’s eponymous label has skyrocketed to cult-favorite status, thanks in large part to its best-selling Penny Loafer (which is a favorite of It girls like Emily Ratajkowski). With the increased demand comes increased responsibility for the designer ... which means more time on-the-go.

“I go to Italy about every three months,” explains Haller on a recent Zoom call with TZR. “I never expected to have to go so often, but as the line's grown, there's just so much that I have to pay attention to. So it's really nice to see people face to face, and it's just good for morale for me to be present sometimes. Also with things changing and growing all the time, I've got to talk to people and have my eyes on stuff.”

And while these quick jaunts to Europe are technically for work, the mother of two likes to maximize the time, even if it’s just enjoying an afternoon alone, a quiet plane ride, or even a solo dinner in an airport terminal. “Here's the thing I love to do that makes me so happy — I did this for the last two trips I took to Italy. In LAX’s international terminal, there’s a Border Grill [restaurant]. I get there super early because I hate feeling stressed by lines. I get a margarita and nachos and sit at the bar and I am just filled with joy. Alone, I can scroll on my phone and eat and drink and then make it to the gate when it’s time. It's so fun for me.”

Ahead, Haller unpacks her travel secrets, from her controversial stance on the carry-on versus checked bag debate to her go-to in-flight essentials.

Carry-on or checked bag?

I've actually recently reverted to being a full checked bag person. The last two trips I took, I had to bring two suitcases just for myself, which is very cumbersome, and it feels overwhelming, because I'm packing a bunch of samples. So one bag's usually filled with shoe samples, or denim samples, and then the other bag has my clothes. For me, I love that freedom of not having to carry anything. So, actually, I hate carry-ons because I hate carrying stuff.

What are some of your in-flight habits?

I just like to do all the things I like to do. I like to have a glass of wine. I stream Succession in the background and watch 20 episodes in a row. It makes me so happy. And then I will work for two hours, then I'll stop, and then I'll work, and then I'll stop. And sometimes I'll work all the way through a flight. I've gotten keen on knowing I need to sleep on the way to Italy, but I can work all the way back. I'm learning to manage my jet lag a little bit in that way.

I'm not a reader on a plane. I get too distracted by being able to watch whatever movie I want. I never watch what I want at my house. My kids watch what they want. Even when I'm watching what my husband and I both want, it’s really what he wants. I'm not getting to always just watch that one movie that makes me happy that nobody else wants to watch.

What are three items we will always find in your carry-on bag?

Oh, I love to clean my bag out fully before I leave, so there's no trash or wrappers, no receipts hanging around. So, I’ll bring my laptop and all my cords and my phone. I do bring a Kindle, but I never read. But I guess if everything was out and I couldn't sleep, I would read. And then just a moisturizer — and I have to take a pill for a thyroid thing.

What are your non-negotiables when it comes to hotel stays?

I just want to be really comfortable and I like to feel warm and nurtured. I feel like I need that. So the taste of the furnishings is important. I don't like things that are hyper modern and I don't like things that don't feel comfortable and cozy. So I tend to stay in more traditional places. I think the fact that I'm also an interior designer hurts because I'm really picky. I like to feel inspired by my surroundings, and that makes me feel relaxed. And if I feel indifferent or cold [about the space], then I just feel cold on the inside.

I stay a lot at The Bowery [when I’m in NYC], and I feel all those [good] things while I'm there. It feels cozy and warm and beautiful. And even from a materiality perspective, I'm geeking out on the sinks, the beautiful, original 1900s pedestal sinks. That makes me happy because it’s very in alignment with what I like.

I've been growing a business for four years, and I don't always take care of myself in the business financially. I'm the one that is the last one to get a paycheck, you know what I mean? So there are things I can do during my business stays, that feel like, ‘Oh, I can treat myself. I deserve it.’ I like to really dive in there because I know I'm shorting myself in other places, so I'm going to spoil myself where I can.

What trip(s) are you planning right now?

I don't have a work trip planned [at the moment]. I'm sure one will pop up probably as we approach fall production, maybe in May or June I could foresee that I might have to go back to Italy. And I will probably take some trips with my family. We're trying to decide on that now. Spring break-ish type. I don't know. We're going to Palm Springs, but that's not really a travel trip.

What place have you visited multiple times? And why?

We just went back to Mexico, my husband and I, and we brought our kids, in the beginning of December. We went to Punta Minta. It was amazing. However, we used to go to Mexico once a year, all the time, like 15 years ago. We just stopped going, basically, when we had kids. And when we went this year, we realized we have to start going back because we had a great time. It was really easy and close. [We were like,] ‘why did we stop doing that?’ We also tend to go to Ojai every year.

Are you an itinerary planner? If so, how detailed do you get and how much will you stick to it?

I'm so not a planner. In the past, I've gone [to New York] and made commitments like, ‘Oh, I'm going to go to this museum.’ But other than that, I really make no promises with my time. Other than dinner — I'll show up for a reservation because that's fun.