Dressing for the Woman I Want to Be

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How One Month in Barcelona Made Me Rethink My Wardrobe:

I’ve always loved shopping, specifically clothes shopping. I remember the excitement of back-to-school clothes, eager to pick out something cute and trendy that would elicit mild envy from my peers. Just kidding — sort of.

As an adult, that hasn’t changed. I still feel a thrill, and honestly, a sense of comfort, strolling through a mall and finding new things to add to my ever-expanding wardrobe. I love mini dresses and even mini-er skirts, crop tops, Levi’s 501s, anything denim, sheer shirts, tight jeans, leather skirts, and anything with cutouts.

But since entering my late thirties, I’ve started thinking more about the way I dress and the way I actually want to dress.

Don’t get me wrong, I like my clothes. They are stylish, generally on trend, and people compliment them. But when I look at my wardrobe as a whole, there is no clear direction or definition. It is essentially a compilation of every possible version of Jenna from the last fifteen years: Club Jenna, Office Jenna, Boho Jenna, Preppy Jenna, Edgy Jenna — you get the point.

Booking a month in Barcelona finally gave me the inspiration I needed to rethink things. Not because I suddenly want to become a different person, but because I want to feel like the most current version of myself when I’m there — and really, everywhere.

More than that, I want to look honestly at this stage of my life and ask what I want my clothes to say about me. As a result, I started purging my wardrobe, no longer using the criteria of whether something technically fit, was tiny and cute, or was something I might wear “one of these days.” You won’t.

Ultimately, the vision I want to project is effortless but chic, stylish but comfortable. I want to dress sexy and flirty without that automatically equaling half naked. I want to stop dressing like a contestant on a reality dating show. Or at least, not dress like one every time I leave my home. I want outfits that can handle a full day of walking, wandering, museum-going, coffee-drinking, shopping, and sitting at a bar with a martini without making me feel like I either gave up completely or tried too hard.

And I figured there was no better place to start than Barcelona.

There is a fantasy of effortless travel style, mostly perpetuated through Instagram, Pinterest, and TikTok: linen two-pieces, lots of white and beige, thin, strappy sandals, a tiny crossbody bag that barely fits an iPhone, golden-hour cocktails, and hair that remains curled all day.

Frankly, unless that woman is being chauffeured from place to place and re-styled and steamed in the back of a Suburban, it is simply not possible to look that flawless while truly traveling.

The reality is more aligned with long days of sightseeing, day trips, supportive shoes, miles of walking, laundry, removable layers, and sweating. The question becomes: how do I balance form, function, and the version of myself I want to bring abroad with the actual traveling I will be doing?

For me, this means choosing pieces that are versatile, comfortable, polished, and sexy but not overly exposed. They make me feel confident and put together but can be styled for an afternoon of strolling or an upscale dinner with just a couple of simple switches. This includes staple items in neutral colors, such as a black midi skirt, a lightweight linen blazer, a  satin dress, neutral-colored linen shorts, wide leg jeans without rips, well-fitted tees and tanks, knitted tops, and light button-downs.

Things like this might sound too practical, boring even, but with the addition of sunglasses, walking sandals, stylish flats, ankle boots, white sneakers, jewelry, and accessories like belts, the outfits gain dimension and become classic and timeless.

Just as important is what I am no longer choosing: items that can only be worn one way, skin-tight clothing, skinny heels, micro minis, and anything whose sole quality is being “cute.” Those days are over!

My goal isn’t to try on a different version of myself in Barcelona or be someone I am not. Barcelona was merely the catalyst to tackle another task on my ongoing quest for self-improvement and growth. I’ve looked at my wardrobe for years, constantly saying “I don’t have anything to wear”, when in fact, I had a lot to wear but barely anything that reflected how I wanted to feel on the inside.

I want my clothing and my style to reflect the woman I am today — or at least the woman I am continuing to grow into.

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About Me

Hi, I’m Jenna – a Los Angeles-based traveler drawn to places with character, history, good restaurants and side streets worth wandering. A Girl Named Gin is my collection of travel guides, reflections, favorite finds and places worth remembering.

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