Balancing the Hard and Soft Sides of Dressing for Travel
This Sunday edition of Consider Yourself Cultured is brought to you by Away.
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Some of my favorite childhood memories revolve around my grandmother. She is, without a doubt, one of the funniest people I know, an entrepreneur, and, most importantly, a woman with a remarkable sense of adventure. When she was just 19, she decided on a whim to live abroad simply to experience it. She has always believed that the opportunity to travel is one of life’s greatest privileges—a belief she passed on to me the day she surprised me with a suitcase and a promise to take me to Paris for my 16th birthday. While we were sadly unable to make that trip when I turned 16, her excitement knew no bounds when I told her I’d finally be going to Paris at 25.
When it comes to travel, aside from having the perfect outfit (which we’ll delve into soon), having the right luggage is crucial. I've often expressed my appreciation for Away, which offers customers durable and stylish luggage and accessories that make traveling feel like second nature. I was thrilled to partner with them. Like my grandmother, I believe that travel is one of life’s great joys, and having the perfect luggage elevates the experience. I have been beyond pleased with my Away Large Softside suitcase—it has been my trusted companion, not only during my trip to Paris but also for my frequent jaunts between Tannersville and the city. I’ve also sung the praises of the Away Large Toiletry Bag, which fits entire bottles of toner and cleanser with room to spare—and, best of all, it can be monogrammed!
Away has unveiled a delightful collection for the holiday season, featuring their go-to luggage sizes and insider packing cubes (a must-have for staying organized) in two vibrant colors: Galaxy Blue and Supernova Silver. The new releases also include a retro-inspired Train Case with a modern twist, along with a passport and travel wallet, and a card case available in a range of fresh colorways, and more!
Naturally, all this luggage had me reflecting on the many lessons I’ve learned about putting together the perfect travel outfit.
I’ve never idolized the airport outfits of bygone eras quite as much as some others. Sure, a few of those storied looks have made their way into my saved photo album, but I never truly gave much thought to curating the ideal travel ensemble. That changed this year, thanks to riding Amtrak nearly every other week, a spontaneous trip to Minneapolis, and, of course, my jaunt to Paris. My astrologer told me in June that my chart was ripe for travel, and I guess she was right.
Becoming a frequent train traveler rather than a flyer led me to realize that crafting the perfect travel outfit comes down to one thing: mastering the art of balance between hard and soft elements. What do I mean by hard and soft? I’m glad you asked. Imagine your luggage. Hard-shell cases evoke protection and security, while soft-sided bags offer flexibility and adapt to irregularly shaped items and the same can be applied to clothes.
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In clothing terms, “hard” pieces are structured, made from durable fabrics designed to withstand the rigors of travel. In contrast, “soft” pieces provide lightness and comfort, creating a cozy balance. While a great outfit seamlessly blends various elements.
In the case of the above look, it may appear purely soft at first glance—thanks to the luscious velour set (which could also double as a perfect hosting ensemble), the softness of the cashmere coat, and the wool sweater draped over the shoulders, not to mention the velvet slippers. However, the hard elements emerge through the structured silhouette of the collarless coat. This structure, combined with the inherent nature of this particular outerwear piece that leans more evening than day, adds a welcome touch of rigidity.
Even the smallest details, like a baseball cap—this one gifted as a memento from a friend’s fabulous wedding—enhance the contrast. By matching the structured elements of the coat, the cap helps ground the look, ensuring it doesn’t veer too far into lounge territory without losing its charm.
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Sweatpants have never really been my go-to for travel. It’s not that I hold any disdain for them (though, admittedly, Karl Lagerfeld’s infamous quote about sweatpants still lingers in my mind). My hesitation likely stems from a reluctance to feel—or appear—too comfortable while on the move. This is where the concept of “hard/soft” dressing proves invaluable, offering a way to elevate casual pieces effortlessly.
One of the easiest ways to elevate sweatpants is to focus on novelty, whether through fabrication or silhouette. Take the barrel-leg shape, for instance—it’s having quite a moment. While I’ve tried this silhouette in denim, it never quite worked for me; I always ended up feeling slightly off. Sizing up in jeans only seemed to accentuate the curves in a way I didn’t like. But in sweatpants, the barrel-leg shape felt entirely different. Sizing up softened the curves, creating a more relaxed, balanced look. Plus, opting for a size up was a wise move in case of shrinkage—and sure enough, they did shrink a bit in the wash.
Pairing these sweatpants with a leather jacket, provided the “hard” element I sought for balance. To further enhance the interplay of hard and soft, I decided to tie a shirt around my waist in lieu of a sweater. While shirting can lean soft depending on the fabric, I prefer the structured feel of stiffer cotton or a denim shirt around the waist. It offers a nice contrast to the coziness of flannel or other softer layers.
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While putting this outfit together, I couldn’t help but think of my boyfriend, who has a certain fondness for Mad Men, which has influenced his approach to getting dressed when he travels. He reasons that, in an ideal situation, the first stop on a trip would not be to a hotel but to a restaurant, and with that in mind, he always tries to wear something he feels would be appropriate for such a setting. In all my years of travel, I’ve never had to deplane and rush into a meeting or meal, but I enjoy imagining what I would reach for in such a situation. Predictably, the first thing that came to mind was a blazer—perhaps a cliché, but there’s no denying its power to instill confidence and its suitability for settings that may require a more dressed-up look. However, I didn’t want something too traditional. I was looking for a bit of flair, which is why I chose this structured number from Tory Burch. It’s unlined and has a canvas-like texture that lends it structure, while the pronounced shoulders add just the right amount of boldness, complemented by the graphic nature of the stripes that remind me of those great blazers from the likes of Romeo Gigli.
Cords, in my opinion, strike a perfect balance between the rigidity of denim and the comfort of softer pants. I’ve been on quite a corduroy kick lately, and I’ve picking up a relaxed pair from Polo Ralph Lauren and a jacket from Toast—I admit, I’m obsessed. This particular pair from Veronica de Piante offers a relaxed fit through the leg and, from certain angles, even appears to flare slightly. I’d recommend a visit to the tailor to ensure they fit just right; I plan to have mine taken up a bit. Unlike the Ralph Lauren pair, these sit higher on the waist—a detail I appreciate, as high-waisted pants always make me feel a bit more poised.
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Similar to the previous look, I found myself thinking again about what one might wear when rushing directly from a flight to a meeting or dinner. Again, I gravitated toward a blazer and corduroy (I did mention I’m obsessed). It may seem a bit whimsical to travel in an off-white or cream blazer, but the texture of the corduroy helps to soften the preciousness of the color. And really, why not travel in white? To further dial down the formality of the blazer, I layered an anorak underneath. I’ve long been enamored with anoraks long before the recent rain gear fixation we saw on the SS25 runway. Part of my love for this particular piece is that it combines the best elements of a hoodie or hooded jacket (namely the hood and shape) but with a utilitarian fabric that goes beyond the standard cotton-blend hoodie.
For the pants, I opted for what THE NEWSLETTER PANTS: the High Sport Kick Flares. These pants are exceptional for a reason—they provide the comfort of leggings but are elevated by their vibrant colors, patterns, and quality fabrication. I remember speaking with Alissa Zachary when she was starting to have more meetings with big box wholesalers. One of my go-to questions for any brand is about their adjacencies—in the context of retail, these are the brands they see their pieces sitting alongside or the ones their customers might shop for in tandem. The first name she mentioned was Alaïa. While she may have listed others, Alaïa stuck with me. Initially, I was puzzled, but anyone who has experienced the power of Alaïa’s knits understands. They accentuate the body beautifully, and whereas some brands' versions of accentuation feel more like constriction, there is always an appreciation for the body in the work of Alaïa—and I’d say the same for High Sport. Apart from Alaïa, I also can’t help but think of Donna Karan—a brand rooted in creating a foundational wardrobe for the modern individual. I see Zachary building her brand with a similar vision and commitment.
When it comes to traveling with jewelry, I always prefer to carry it by hand rather than stowing it away in a carry-on or checked bag. It gives me peace of mind to know that these cherished pieces are close to me. I also tend to wear as many of them as is practical for travel—stacking multiple rings on my fingers and layering as many necklaces as I can. This habit stems from my own anxiety about items getting damaged or, heaven forbid, broken. Keeping my jewelry visible and on my person simply makes me feel more at ease.
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Looking back at my airport bathroom selfies or snapshots taken just after stepping off a train, I noticed something: if I wasn’t wearing drawstring pants or elasticated silk-blend trousers—I was wearing jeans. For the longest time, jeans were simply something you needed to have for me, I wore them out of necessity rather than excitement. That changed about a year ago when I developed a newfound appreciation for denim. While I’ve generally favored vintage pieces over newer releases, I’ve found my denim bliss in these Alex Mill relaxed jeans.
My main gripe with modern denim has always been the stretch—it often compromises the structure and feel for me. I prefer my jeans on the stiffer side, or at least a pair that feels broken-in yet regains its structure after a wash. These jeans sit just below the waist and strike the perfect balance between slouchy comfort and a relaxed fit that doesn’t drown me in fabric.
To complement the jeans, I decided to layer up on top—a turtleneck beneath a silk button-down shirt and a sweatshirt. To add a touch of sophistication, I finished the look with a playful brooch designed to hold a flower.
I’d love to hear—do any of you have go-to travel outfit formulas? Let me know in the comments or in the chat!
Talk soon!
xx
JJ
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"I found myself thinking again about what one might wear when rushing directly from a flight to a meeting or dinner." Very good packing mentality.
Your travel style is perfect because it's so perfectly you. Sometimes I feel you dress on a mission -- to restore beauty. Coast to coast. I am grateful for it.