Do you find yourself overwhelmed by the urge to revamp your entire wardrobe before each trip? The excitement of exploring a new place or revisiting a beloved destination often comes with the temptation to buy new clothes, shoes, and accessories. It’s a common pre-travel ritual, fueled by anticipation. However, the reality is that many of these carefully chosen pieces often end up unworn back home, gathering dust in our closets. Stylish travel clothes can quickly drain your travel budget, and let’s be honest, they aren’t always the most practical. When exactly will that elegant shearling coat, perfect for a Swiss getaway, get another outing in sunny San Diego? Back in our daily routines, comfort reigns supreme, and much of our meticulously curated closet remains untouched. Perhaps, like me, your fashion passion is more of an indulgence, a delightful guilty pleasure often satisfied by the thrill of thrifting. I justify it as a ‘hunt’ for unique finds, supporting local charities, and diverting perfectly good garments from landfills, all while sidestepping the ethical concerns of fast fashion. Yet, I understand that thrifting isn’t for everyone.
A few times a year, I escape my desk and venture out to my favorite second-hand shops, especially those with curated boutiques showcasing better brands. It’s a fun outing, whether with friends or as a guilt-free break from my home office. Thrifting can even become part of the travel experience itself. Exploring vintage stores with friends in new cities is always a joy. Sometimes, finding stylish travel clothes while on the go – like a desperately needed raincoat in rainy New Orleans or waterproof sandals in the Bahamas – is a matter of practicality rather than just fashion.
Then there are those special trips – weddings, parties, reunions – where the mental fashion show begins weeks in advance. The imagination runs wild with visions of perfect outfits for every occasion.
Entry Level to Fine Fashion Finds
My introduction to quality accessories began with a Baggalini tote discovered in a Goodwill Boutique. Over the years, I’ve become a loyal customer. The model I favor is perfect for carrying all my tech gadgets and conveniently folds flat in my carry-on suitcase. Similarly, a pair of almost-new Dansko sandals from a Cancer Center thrift shop opened my eyes to the world of supportive yet surprisingly lightweight footwear, a blessing for walking tours and long travel days. Given my work’s mobile nature, I’ve since invested in SAS sandals and Nordstrom winter boots. Those Dansko sandals were lifesavers during long days exploring Petra, Jordan, keeping my feet cool and blister-free, and they are stylish enough for everyday wear back home. The snow boots are ready for my next winter adventure, proving that practical travel finds can seamlessly integrate into your regular wardrobe.
When to Experiment with Stylish Travel Clothes (Hint: Not Just Before You Leave)
Travel is often associated with fantasy. It’s the exciting ‘courtship’ phase before the realities set in. Just like relationships, travel too requires effort to maintain the dream while staying grounded. I’ve previously written about thoughtful packing strategies, but this is about nurturing the travel dream without losing touch with reality – and maybe adding a touch of humor. The best time to experiment with new fashion trends isn’t right before a trip, but at home. If you’re comfortable and confident in cut-off jeans, by all means, pack them. But don’t pack them based solely on a fantasy of looking effortlessly chic strolling through Santorini, only to cringe at your reflection in a shop window. Sometimes, the funniest travel moments come from fashion missteps and realizing we’ve packed for an idealized version of ourselves, not the real, comfortable traveler we are.
Pulling It All Together – Unexpectedly
Sometimes, we buy pieces with a vague intention of wearing them ‘someday.’ We’ve all been there, right? The real fun begins when those pieces unexpectedly come together to create an outfit you hadn’t even imagined. This post was sparked by an upcoming country wedding trip. I wanted something special to wear and found myself near a fantastic consignment shop recently. I discovered a vintage-cut dress that fit perfectly, and upon returning home, I realized it completed an ensemble by pulling together several items already in my closet! (And no, I’m not channeling Carrie Bradshaw – I have one very full, but single, closet.) This dress is now the centerpiece of my summer travel wardrobe. Crucially, I’m ‘test-driving’ it at a local farm-to-table dinner before packing it, ensuring it’s as comfortable and practical as it is stylish. This approach adds a touch of humor to travel planning – sometimes the best outfits are happy accidents, not meticulously planned purchases.
It’s All in the Past – Or Is It Timeless?
My fascination with vintage fashion started early. My mother was a professional dresser in the 40s and 50s until our family moved from San Francisco to suburban Southern California. Suddenly, it was hello to flip-flops and Bermuda shorts, and goodbye to tailored hourglass silhouettes and elegant silk and linen layers. While raising four children, some of her cherished pieces were stored away in our ranch house. (Perhaps this is where my thrifting habits began?) Luckily for my sister and me in high school, Mom allowed us to wear her suit jackets, riding pants, and Peter Pan collar blouses. Later, I inherited boxes of vintage jewelry and scarves from aunts, expanding my collection of stylish relics from the past.
Those were the days when my friend Julie and I devoured Vogue and teen magazines for style inspiration. We’d hunt for affordable ‘knock-offs’ during trips to Los Angeles. It was exciting for Catholic high school girls who spent weekdays in uniform. After graduation, I worked in a ‘boutique’ in a new mall and spent my earnings on bold colors, hot pants, and mini-skirts. Julie, a talented seamstress, created her own concert dresses, and I still remember her Mary Quant-inspired look – Cher bangs and a high-necked silk mini dress. We were never true hippies; more into the mod style and Twiggy’s iconic look.
Yes, I know these fashion references might seem obscure now. But surprisingly, in a recently renovated La Jolla mall, store windows are showcasing crop tops and high-waisted shorts – styles remarkably similar to what my mother wore! Fashion, like humor, often circles back around.
A Simpler Time and Luggage Woes – Embracing the Funny Side of Packing
Think tropical drinks, the Tommy Bahama aesthetic, and Jimmy Buffett’s Parrot Head vibe. The current fascination with all things Tiki reflects a longing for simpler, carefree times, where life revolved around margaritas and grass skirts. This desire for relaxed escapism is strong, but packing for it can be a challenge. How do you fit crisp shirts, long skirts, and platform shoes into limited luggage space? The key is to build your travel wardrobe around a few versatile pieces. Mix and match, and always check if your accommodation has an iron! You don’t need to dress like you’re stepping onto a stage, but cultivating a personal sense of style is important. I find humor in unexpected pieces that work well for travel, like my Harley Davidson biker shirt, which pairs equally well with cropped pants or a skirt – it’s comfortable and travels beautifully. A well-fitting skirt can be the foundation of stylish travel clothes, helping you avoid the typical tourist look. The funny thing is, sometimes the most stylish travel moments are when you least expect them. Dress up or down – sneakers and platform pumps can transform an outfit. Add a neck scarf, and suddenly you’re channeling Audrey Hepburn – or at least, feeling a bit more glamorous amidst the travel chaos.
Got Some Catching Up to Do – Finding Humor in the Mirror
It’s been a long and stylish journey, but when I look in the mirror now, I see my middle-aged mom staring back. Despite wishes to inherit my father’s slimmer physique, it simply hasn’t happened. Pear-shaped is my reality, unless extreme measures are taken – starvation, hours of daily exercise, or surgery. None of which are appealing.
However, I refuse to relinquish my hard-earned sense of style. It’s just evolved. I embrace Coco Chanel’s wisdom: “After 40 nobody is young, but one can be irresistible at any age.” Recent articles and documentaries celebrate older women and their freedom to experiment with stylish travel clothes and everyday outfits. That’s my goal – to pack that spirit of fun and fearless style into my travels well into my 80s! And perhaps, find the humor in the inevitable fashion mishaps along the way.
Minimalism – The Funny Freedom of “Travel With the Clothes on My Back”
With all this talk of fashion and shopping, it might be surprising to learn that I advocate for simple living and strive to minimize my possessions. I admire the minimalist trend and the energy it frees up by focusing only on essentials. My travels to Japan have reinforced this philosophy. Aspects of Buddhism and Shinto, emphasizing nature, ancestry, and rejecting materialism, deeply resonated with me. Yet, living in a fast-paced, consumer-driven society that’s often disconnected from nature creates a constant balancing act. Finding personal equilibrium is an ongoing, individual journey.
So, when I bring home a ‘new’ thrifted item, I make it a practice to let go of something else – a process that can be surprisingly liberating. Have you ever hosted a clothing swap or gifting party with friends? It’s incredibly soul-satisfying. I recall my younger sister-in-law’s delight when I gifted her a sequined cocktail dress from my mother. There was no chance I’d ever fit into that size 7 sheath again. It brought joy to both of us. Looking ahead to future stylish travel clothes, I’m excited to continue thrifting and gifting – and perhaps, embracing the humor in the idea of truly traveling light, with just the clothes on my back, and a suitcase full of funny stories.
Where to Find Stylish Travel Clothes and Accessories (and Inspiration for a Laugh):
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