No. 45

Your favorite outfits aren't going anywhere (literally)

Jul 22, 2025

I have been deeply uninspired for the last few weeks and I couldn’t seem to figure out why. Is it because my creative energy is depleted with my home redesign project, and I’m just out of juice? Is it because I just don't really care anymore? Is it because its an overcast week in the city?

It turns out, it’s none of these.

The real problem I'm facing is that my favorite outfits are vacation outfits, and I’m not going on as many vacations right now.

For the last decade, I’ve spent the better half of each year traveling. The cowboy boots and floral skirts that are both feminine and pared-down that look perfect in the mountains? The linen dresses that keep me perfectly cool in balmy summer weather? The statement jewelry that feels perfectly appropriate for evening aperitifs in a foreign city? These pieces have become the backbone of my wardrobe (at least, my favorite items: bright, colorful, delicate, dramatic), curated specifically for a lifestyle that I have mostly eschewed this summer in favor of more local pursuits.

My life has taken a slightly different shape lately: I’m more deliberate with the trips I go on (opting for bucket list trips instead of being a “yes woman”), I have a cat, and I’m honestly just a lot more connected to my San Francisco community and landscape than ever before. It feels really good to finally have the time to do all of the things I’ve had on my list for years around here: from cold plunges, to new restaurants, to pool clubs, to tennis dates, to vintage shopping. But as this shift has dovetailed beautifully with an appreciation for my home city and a balanced lifestyle, its also left me with more questions than answers about who I am in this phase of life.

The Vacation Outfit Trap

There’s something intoxicating about dressing for vacation. The stakes feel higher (for some reason?) and we have the opportunity to play with different climates (cold and wet in San Francisco? Good thing it’s dry and hot in Sun Valley!), colors (with a tan, I can wear ANYTHING), and personas. When I pack for a trip, every outfit gets planned with the reverence typically reserved for special occasions. I’m unencumbered by the weight of daily life, I can play dress up because I AM dressing up.

Somewhere along the way, I’ve become so accustomed to dressing for experiences that everyday life feels woefully inadequate as a backdrop for my favorite pieces. Home has become, over the last decade, so much of a reprieve from excitement, that I've started to treat fashion in the city I live in as irrelevant and unimportant. When you combine this frantic travel with work from home (which I have done, every day until recently when I started working from a club a few times a week) since 202. That’s five years of daily dressing for the city that just wasn’t really happening.

When you travel 6, 7, 8 months out of the year, the time you spend at home is, mercifully, used as recovery time. But when vacation becomes more and more a special treat, what am I doing to make the everyday feel special?

All of a sudden, I’m not so sure who I am at home in San Francisco. I’ve fallen into the trap of saving my best pieces for these “special occasions” – except my definition of special has become increasingly narrow and tied to geography. I don't have a “San Francisco look,” and the more time I spend at home in San Francisco, the more disconnected I feel from my flowing mountain dresses, my sparkly European skirts, my fur coats for much colder cities, and my oceanic jewelry.

The Psychology of Place-Based Dressing

There’s legitimate psychology behind why we dress differently when we travel. We’re playing a version of ourselves that feels more elevated, more intentional, more alive. Travel gives us permission to experiment, to be bolder, to wear things we might second-guess at home. The anonymity of a new place removes the social pressure of repeating outfits or adhering to the unspoken dress codes of our daily routines (and, of course, microclimates).

When you’re wandering through a new city, that vintage silk scarf feels like it belongs - the colors complement the architecture, the weight of the fabric suits the climate, the entire combination feels harmonious with your surroundings. When you're having dinner at a seaside restaurant, those statement earrings don’t feel precious - they feel appropriate for the setting and the version of yourself that emerges in that place.

But what happens when your surroundings are just...normal?

The solution isn’t to stop buying beautiful clothes for travel (heaven knows that’s not happening!!). Instead, it’s about expanding our definition of worthy occasions and reimagining how our favorite pieces can serve us in everyday life.

And I’ve learned that I need to push myself a little bit, and maybe you do too. I’ve started doing “fancy Tuesdays” - deliberately choosing pieces that I would pack for a trip and wearing them for absolutely no special reason at all. That silk blouse I bought in Paris? Perfect for an afternoon at my co-working space. Those handwoven pants from Mexico City? Ideal for coffee with a friend.

Creating Your Own Worthy Moments

This change in mindset represents a larger shift for me: finding comfort in routine. Though I realize not all of you may have the EXACT same experience (the amount of travel I was participating in for the last decade was nothing short of psychotic), most of us can connect with the determination of normal life as unworthy of pomp and circumstance.

Why should physical location determine whether we deserve to express creativity? What does it to do the part of our brain that creatively problem solves when we refuse to flex that muscle on a regular basis?

When we restrict our creative expression to certain locations or occasions, we’re essentially putting our creative problem-solving abilities into hibernation. The same part of our brain that figures out how to style a vintage scarf with modern pieces, or how to make bold jewelry work with a casual outfit, is the same part that tackles challenges in other areas of our lives. Creativity is a muscle that requires regular use – when we save our most thoughtful styling choices for vacations and special events, we’re depriving ourselves of daily practice in visual problem-solving, color coordination, and self-expression. It’s like being a painter who only picks up a brush twice a year; eventually, the instincts get rusty. By artificially limiting when and where we allow ourselves to be creative with our appearance, we're not just missing out on feeling beautiful in our everyday lives – we're weakening our overall capacity for creative thinking and innovative solutions.

I’ve started asking myself: what would I pack for a weekend in Sedona? What would I wear for brunch in Seoul? There’s no reason I can’t wear those pieces for lunch with a friend in San Francisco. The flowing pants that feel perfect for a desert afternoon work just as well for a Saturday morning in my neighborhood. The delicate jewelry that seems right for a special dinner out doesn’t become wrong just because the restaurant is local instead of foreign.

The key is recognizing that the magic was never really about the destination - it was about choosing pieces that make me feel like myself, regardless of the zip code.

This isn’t about being impractical or overdressed for your circumstances. It’s about refusing to gatekeep your own sense of style behind travel plans and special events. It’s about remembering that you are worthy of beauty and thoughtfulness in your daily existence, not just when you're living the most glimmering version of your life.

Some of my most cherished pieces now have new stories – not just memories of where I bought them or the exotic locations I wore them, but quieter stories of ordinary days when I chose to honor myself with something beautiful.

My asymmetrical silk Acler blouse used to be worn with pencil skirts for dinners in Copenhagen, but now reminds me of our first date in our new home. My archival highlighter-yellow Chloe coat now reminds me of a new wine bar where I shared laughs with a friend.

Moving Forward

I’m learning to pack for my current life with the same care I bring to packing for a trip. This means asking myself: What do I want to feel today? How can my clothes support the experiences I'm creating right here, right now?

The shift is simple but profound: instead of asking “Is this outfit special enough for this occasion?” I've started asking “do I like how I feel in this?” If the answer is yes, then Tuesday afternoon is worthy of those cowboy boots (frankly, some of the best shoes you can wear in this city!). A normal workday deserves that delicate silk blouse (even if I have to dry clean it…). Bi Rite can handle my statement earrings (sometimes, you even get a surprise compliment).

After all, if I’m going to be deeply inspired again, it won't be because I’m waiting for the next trip. It’ll be because I've remembered that every day offers opportunities for beauty, intentionality, and the luxury of feeling like the best version of myself.

With That - Making the Beautiful Practical

What was once styled for Barcelona can be perfect in San Francisco: just swap the sandals for sneakers and pop the sweater on instead of wearing it over the shoulders.

It just takes a little bit of effort to make something feel more casual and wearable: for example, an oversized denim button down on top of an Agua Bendita dress that feels more at home in Nantucket on its own.