The Art of Wearing It Again (and Again)

Lessons from Living out of a Suitcase

I recently returned from a seven-week trip visiting family in Italy and noticed something interesting: it’s easier to get dressed when I’m living out of a suitcase. Outfit repeating is liberating.

Over the past few years, as I’ve edited my closet and focused on pieces that work for me, I’ve become a much better packer. Now, I only bring what I already wear on repeat, nothing more. I learned this lesson the hard way years ago when I packed new items to “try” on vacation. It was a disaster. Those pieces ended up as dead weight in my luggage while I reached for my tried-and-true favorites.

These days, I pull out my regulars, add a few impactful accessories — handbags, belts, necklaces — and that’s it.

On this last trip, I only brought three pairs of long pants, but they were pants I could wear repeatedly in different ways, and they all worked with every pair of shoes I packed (critical!).

When I got home and unpacked, it hit me how much harder it is to get dressed with a full closet. I forget half of what I own and find myself thinking, “Why do I have nothing to wear?” Which I know isn’t true, because I just spent weeks putting together plenty of outfits from one suitcase.

Find your formula

Travel also made me see which outfit formulas work for me, which pieces are my true wardrobe heroes, and how to rely on them more often.

It also made me think more critically about what clothes are worth investing in. Clothes made from natural materials, like cotton, last longer and can become true workhorses in your wardrobe. Two of mine on this trip were a pair of cream Levi’s 501 ‘90s jeans and a striped button-down Polo.

I wore them constantly, and they can handle it. They feel good, the material is sturdy, and you can tell they’re well-made. For affordable, durable pieces, I look to classic brands like Levi’s and Polo—but I still check the material content before buying.

Striped Polo + Levi’s in Venice

And again in Milan

I am sensing (and maybe hoping for) a shift in our collective mindset: moving away from always needing new, fashion-forward items and focusing instead on classic basics — the true foundation of a wardrobe.

This brings me to a quote from

Max Berlinger

where he cites trend forecaster Michael Fisher:

“We thought post-pandemic would bring a new Roaring Twenties—excess and formality—but consumers chose the opposite: fewer decisions, more basics. They’re exhausted and in no mood for fashion with a capital F.”

In a world where we can get anything at any time, choosing timeless basics over the constant chase for “new now” can be a kind of rebellion.

Reframing limitations

Humans need limitations to thrive, especially in the creative process. Every creative act has constraints, and embracing these limitations can lead to creative breakthroughs.

I love this quote from Long Live by

Erika Veurink

where she says:

“There’s a creativity in limitation, a feeling you might get when you travel and only have a certain number of ways to wear a single sweater. It helps us develop a relationship with the items we own. And this makes us feel confident, inspired, even at home in the familiarity of our closet.”

When I travel, I have a set number of pieces to play with, and in that limitation, I explore, experiment, and put each item to the test. You push past the perceived limits of a garment, and if it’s a good one, you end up loving it even more.

There is nothing more satisfying than getting a stain out of something I wear on repeat. I like to imagine I’m a woman in the ‘60s, and that white button-down couldn’t just be replaced, it had to be saved, because it was one of my signature pieces.

There’s something meaningful about loving an article of clothing so much that you’ll fight to save it from the landfill.

Maybe we’re onto something here. Maybe it’s time to think of our clothing as more than just textiles, but as steady friends - there when we need them most. You wouldn’t discard your favorite sofa you spent a year deciding on after a season or two, so why do we do it with our clothes?

The more time and intention you invest in making the right purchase, the more you’ll want to hold onto it.

I propose a challenge

You can practice outfit repetition by shopping your closet. Do you have a birthday party or event coming up and are planning to buy something new? Try to style something you already own instead. Pull out your accessories, play with shoes, hair, and beauty to make an outfit feel fresh again.

A friend of mine recently did this. She has a wedding coming up and was ready to shop online, but paused to check her wardrobe first. She ended up finding something perfect to wear and was so excited she couldn’t wait to tell me. She got a rush of endorphins — not from buying something new, but from rediscovering a piece she already owned. Plus, she saved about $300 in the process.

We’re so wired to get dopamine from new purchases, but what about getting a hit from rediscovering something you already invested in? It’s proof that we can rewire our reward system.

Saving money can bring a longer-lasting, more satisfying reward than spending it. While spending is easy, saving takes discipline. But as with most hard things, the payoff is so much greater.

✨ Saving With You,

Allison

Loving this content but want to go deeper? Wish you had a friend for your no-spend challenges? Join us in the chat for support, encouragement, and plenty of money-saving inspo. 💸