How to Pack a Hat Without Damaging It, According to Travel-Obsessed Milliner Molly Yestadt

The up-and-coming designer reveals her tricks of the trade.


Molly Yestadt, the designer and founder of Yestadt Millinery, is a self-described city person. So, when she was able to choose a destination for her inspiration trip, as part of the CFDA Fashion Incubator‘s partnership with W Hotels, she selected Bangkok, Thailand, a bustling city with a population of over 8 million, instead of a beachy resort. “I am interested in big, messy cities that have a lot of history, and a history of craftsmanship,” the native New Yorker explains. Here, she explains what most inspired her about Bangkok, the other cities she’s excited to visit, and how to pack a hat without crushing it on an airplanes.

As a member of the CFDA Fashion Incubator program, you were able to choose a trip to a W Hotel anywhere in the world for an inspiration trip, and you chose the W Bangkok. How did you make that decision? I think Southeast Asia has always been intriguing to me because the colors are so different, but part of the reason I have been wanting to go to Bangkok specifically is I am interested in big, messy cities that have a lot of history, and a history of craftsmanship. I’m a city person, so it’s always interesting to me to see crowds, when everyone’s together, and what that looks like. I’m also very interested in architecture and design–the way the temples are built, the way the boats are built, the way the markets are developed… it’s very interesting and so different from what I grew up with, so that’s a big draw.

I think it’s just so inspiring to be able to really experience a place with so many different foods and smells. I always feel whenever I travel there’s a lot of smell that comes into play, which sounds weird. But whenever I’ve done big trips it’s a big part of it. The air is different, the light is different and that’s something you only experience when you are traveling, rather than looking at magazines or pictures or something like that. That’s the fun part.

What place were you most excited to see? Wat Samphran, a [17-story Buddhist temple outside of Bangkok]. That’s one I’ve been researching for a long time. It’s amazing. There’s not a lot about it online, but I did some deep research on temples surrounding Bangkok and I found like an image of it and I was like, “I don’t know what this is but it looks unbelievable.” It’s decorative, but it’s architectural and it’s like this spiritual mecca. I can’t think of anything else that I’ve seen that’s so outrageous looking. It’s wrapped in a dragon!

Wat Samphan

What other cities are you inspired by at the moment? The other place that’s been on my bucket list for a long time is Istanbul, Turkey. It has an amazing architectural history, unbelievable food, great markets, specific textile developments, religion and culture… it all happens there. Marrakech, Morocco, would also be unbelievable. Lets make that happen.

How will the ways in which Bangkok inspired you come through in your designs? A lot of the inspiration that I start with is color and lines and I think that comes into play with architectural elements and things like that. I think that at this point our customers are very well traveled, so I think our hats and accessories have to perform in a lot of different scenarios, and I think one of the key things is being able to travel. One of the questions I always get from customers is, “How do I travel with my hat?” But I don’t think it’s too hard to travel with hats! We make roll-up hats that are made for travel, but the fact is that you can travel with any hat. It’s definitely a design challenge to keep in mind, though. Like I know that our girl is not precious about her things, so they just have to perform to some extent with the lifestyle.

The Amphawa Floating Market.

So what are your tips for how to pack a hat? We have a roll up hat that’s awesome. It’s easy — the band is elastic, so you can just roll it up and put it in a tote. It’s our best seller. For things that are more structured, like a structured straw, or something that’s a little bit heavier like felt, I like to bring a tote on the plane with me and put the tote under the seat. I don’t put them in the overhead, because they get smushed around, so that’s how I travel with it. I don’t travel with hat boxes, because the round ones don’t fit in the overhead. I’ve carried big drums before when I’ve gone on meetings, and that’s awesome because you can check that and it’s not going anywhere but I wouldn’t anticipate that it’s something most people really want to travel with! The other trick that I have is if you have a hard suitcase you can put the hat upside down in your suitcase and put a t-shirt in the crown. And that’s easy. I think it can get intimidating, but once you do it you’re like, “oh, no big deal.”

Is that the most common thing people ask you? I think that’s the number two question. The number one is how do I know what size I am?

How do you help customers figure that out? If you have a measuring tape, you can measure your head. We are getting custom tape measurers, which I am really excited about. I am putting a button on the website so if people don’t know their size we can send them a tape measurer! There’s a few tricks as far as sizing goes – in my opinion, I think it’s better if it’s a little bit big. If it’s too small, you can’t get it on. So if it’s a little bit big, you can put milliner’s tape on the inside, or you can also pin your hair, even just adding a little twist with a bobby pin is a great trick. If a hat’s a little big there’s more leeway.

Pak Khlong Market.

What are the hats that you wear most regularly? I wear our baseball caps a lot. Like a lot. All the time. We’ve done them in leathers and really beautiful, supple materials. And in the summer I wear the samba hat, the striped straw. That’s my go-to. It’s not precious, in a way.

How about when you’re traveling? I always travel with a baseball hat and something that’s a little more sturdy, like if it’s a straw I’ll bring something that’s a little hearty that I know won’t get crushed or collapse. And I’ll bring a sun hat if it’s a nice sunny vacation.

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Aurora James produces all of the pieces for her footwear line Brother Vellies in Africa—so naturally, she’s on the road at least every other month for several weeks at a time to meet with artisans and get inspired. At this point, the designer has packing down to a science. “I usually pack thirty seconds before I’m out the door—as an accessory designer, I usually roll with like 7 pairs of shoes, but it’s part of the fun. And about 8 dresses. I never bring anything black with me,” she says. “Why would you travel and wear black? It’s like a waste of life. You have to bring color, you can wear black in New York.” Her key to traveling light? “I totally utilize the hotel’s cleaning services. It’s shocking to me how many people do not!”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Model-turned-fashion designer Thaddeus O’Neil is an avid surfer—and takes sunscreen really seriously. “It’s essential. Neutrogrena is one that I bring a lot. I use, like 60+ on my face, for sure. I also put zinc on my face, because when you’re out on the water the sun is so bright. I look almost tribal, covered in white.” Other travel essentials include a surfbord, lots of books (“I’m not really a kindle person.”), a journal, sandals, sunglasses, a hat, a watercolors set, and plenty of his own designs. “I wear my own brand 90% of the time,” he says. “Look at these pants! They’re made for travel.”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Korean-born, New York-based women’s wear designer Ji Oh lived in London for years—but her favorite place to shop is in Sweden. “Whenever I go to Paris for work, I go to Sweden for two or three nights to shop. I buy a lot of t-shirts. Like, a lot. They are really well made, the fabrics are amazing, and the cut is never off. In other countries, quality really varies depending on the price, but nothing is ever bad in Sweden.” She also likes to pick up little tchotchkes, such as keychains or bathing suits, when abroad. “They aren’t necessarily rare, but they are special to me!”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Molly Yestadt, the founder of luxury hat label Yestadt Millinery, always wears baseball hats and a scarf on a plane. “If I take a nap, I just pull the hat over my face and then you don’t get bothered!” she says. Yestadte also has advice for how to bring hats on a plane, without ruining them. “You can wear it, or put it in a tote under the seat in front of you or in an overhead compartment, or carry in a hatbox—which is fabulous! We also make packable pats, that can go in a suitcase with a t-shirt in the crown. It’s classic, but it’s stable and it works!”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Daniel Dugoff, the founder of New York-based men’s wear brand DDUGOFF, makes clothes for ”normal American guys who are interested in well-made products, but have a fairly casual lifestyle.” So it makes sense that his favorite mode is pretty low key. “I’m not really a yacht guy, I really like trains,” he says. “There’s something really nice about traveling from city center to city center, instead of taking a cab an hour outside of a city, waiting at an airport for two hours, and flying somewhere just to get back into a city.” Whether on a train or a plane, Dugoff likes to pack light. “I’m kind of an anxious traveler, so I try to bring as little as possible. I never check a bag unless I have to.” He had to make an exception for the trip to Mexico, though. “I wanted to bring a lot of sunscreen,” he laughed.

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Jason and Julie Alkire, the design duo behind women’s wear label Haus Alkire, have been married for nearly twenty years—and in that time they’ve gotten their travel regimen down to a science. “We always take a carryon with some things in it on a plane. A fresh pair of clothes and the three things you each would need to get by for the full trip,” Jason says. “Just in case.” For Julie, that means a versatile Little Black Dress, of their own creation, a red MAC lipstick and “OG black chap stick, it’s like a lip primer,” and Bare Minerals foundation. “If your bag gets lost–you can throw on red lipstick look great.”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Women’s wear designer Charles Youssef worked for Calvin Klein, Ralph Lauren, Gareth Pugh and Cerruti before launching his eponymous collection in New York, in 2014. While running his own business keeps him local most of the time, the young fashion designer is lusting for an inspiration trip to Tokyo or Kyoto, to see the beautiful buildings and architecture. When abroad, he relies on a simple uniform of a “black t-shirt, some black pleated trousers and glasses.” For warm weather, he swaps out the pants for pleated shorts and packs extra grooming products. “I bring a lot of moisturizer, from Shiseido Men’s, and also use Neutrogena moisturizer with sunscreen in it.”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Alexandra Alvarez, the 29-year-old designer of bodysuit brand ALIX, designs a body-conscious product—but loves traveling in oversized pieces that still look chic. “On planes, I always wear a t-shirt; culottes, because they are big and comfortable but still look decent; a sweater; and close-toed shoes. If not, I have socks in my bags so I can change on the flight.” Once she arrives at her destination—she lives in a linen button-down shirt, tied at the navel. “The best one I ever got was at Massimo Dutti, in the men’s section. It was this white linen shirt—the best ever. I wore it all summer long last season, until the drycleaner misplaced it.”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Michael Miller and Katie Deguzman, the duo behind sustainable jewelry brand K/LLER COLLECTION, met as students at Parsons—and see eye to eye on just about everything. When asked about the one item they would never wear on a plane, both shouted in unison, “Heels.” “I made that mistake once,” Katie said. “But then again, I’d never wear Uggs either.” “I always wear drop crotch jeans, an oversized shirt, a giant scarf, and some sort of cool slip on shoe,” Michael added. “And tons of jewelry,” Katie said. “I love how you can now go through the 3-d scanner with all your jewelry on, and I don’t have to take it off!”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

Tim and Dan Joo, the brothers behind accessories brand Haerfest, are always thinking about travel with their designs. “Our backpacks are for someone who has a coffee in one hand an an iPhone in the other,” Tim says. But they certainly understand the need to unwind and disconnect. In order to handle the New York grind, the brothers always add a day or two to a business trip, Dan explains, “to visit any museum or restaurants we wanted to go to. It’s all about work life integration.”

Photo by The Coveteur, courtesy of CFDA and W Hotels.

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