9 Questions to Ask Yourself Before Buying a New Vacation Wardrobe
We’ve all been there — on a trip, or right before one, swept up in the excitement and just HAVE to have that one item. But the pitfall of impulse buys is a wardrobe overflowing with things we rarely wear. After a recent spring cleaning where I got rid of hoodies from all over the place (I was cold when I bought them, okay?), I noticed a pattern in everything I was letting go of.
With a greater appreciation for quality over quantity, here are the questions I ask myself before adding anything new to my wardrobe.
1. Am I only buying this because it’s 90% off?
The allure of a massive discount is real — it’s like a siren song pulling you toward that “bargain.” But saving money on something I’ll never wear isn’t saving at all. It just takes up precious space in my closet and clutters my headspace when I’m getting ready in the morning.
2. Does it actually bring me joy?
Taking a cue from Marie Kondo, I’ve embraced the idea of joy-sparking items. Am I genuinely excited about this, or am I just buying it because I walked into a store and didn’t want to leave empty-handed? If it doesn’t light up my day, it’s probably going to gather dust in the closet.
3. Will I wear it more than once?
If there is one tip I have, it’s THIS! Versatility is everything. I ask myself: can I actually wear this in multiple settings? Or am I picturing myself in some gorgeous ball gown “just in case” I get invited to a ball someday? Save the closet space, save your wallet and your sanity — rent it instead.
4. Am I buying this just because everyone else has it?
There’s nothing wrong with hopping on a trend, but do it because you genuinely like it, not because you don’t want to feel left out. Are bootleg jeans back? Do I have any real intention of wearing them? Pass. Trends come and go, but my personal style is here to stay. I’d rather invest in timeless pieces — or if I want to try a trend, rent it first and see if I actually like it.
5. Do I already own something similar?
It’s easy to forget what’s lurking in the depths of my closet. Before I buy something new, I make sure it’s not just a duplicate of what I already have. “No, Carolyn, you don’t need ANOTHER hoodie.”
6. What am I willing to get rid of?
Every new purchase deserves a closet realignment. I think about what I’ll say goodbye to, so I’m making room for the new instead of just piling on more. Have I worn this in the last six months? Is it worn to pieces? Do I already own something like it? If you’re feeling brave, get rid of more than you bring in.
7. Is this an emotional purchase?
We’ve all shopped as a form of therapy. But emotional buys tend to lead to regret. I try to pause and ask myself honestly: is my heart driving this decision, or my head?
8. Does it actually fit, and is this really my color?
Fit is non-negotiable. Skip anything you’re buying on the hope it “might fit someday,” and stick to pieces that flatter your body as it is right now. If you don’t feel good in it, you’ll never wear it — and the same goes for color. I once bought a beautiful coat I never wore, because sadly I look like the living dead in the shade of lavender- despite it being a gorgeous color, I just can’t pull it off. Know your palette and stick to it.
9. How often will I actually use this?
Practicality wins. I try to prioritize pieces that genuinely fit my lifestyle, so they earn their place in my closet through frequent wear — not just good intentions.
What to buy instead of clothes
Here are three things I’ve never once regretted buying while traveling:
Jewelry. If you’ve visited somewhere special and want to remember it, a one-of-a-kind piece is worth it — pearls from Tahiti, greenstone earrings from New Zealand, a handcrafted olive branch set from Greece. They take up almost no space, spark great conversations, and unlike clothes, good jewelry can be passed down for generations.
Postcards. I send myself a postcard from every place I visit. It’s like a travel diary I can look back on, and they’re small enough to tuck into a scrapbook for later. Pro Tip: try to find a post office early so you’re not scrambling for stamps. And be sure to ask for international postcard stamps. If you’re in a hurry, most hotels will mail them for you if you have postage attached already
Magnets. You can find these almost anywhere, and they take up no space at all. I’ve put together a whole magnet board of every place I’ve been.
But what if you actually want new clothes for the trip?
I’ve got you. I’ve discovered the joy of renting clothes — I personally use Rent the Runway, though there are plenty of other rental services out there too. It’s like having a revolving closet full of options, without the commitment or the hassle of upkeep. No ironing, no dry cleaning, no washing — just send the pieces back when you’re done, and your space stays clutter-free while your options keep evolving.
By weaving these questions into how I shop, I’ve built a wardrobe that reflects my actual style and values — not just whatever trend is passing through — and I still get the joy of getting dressed up for a trip.d a wardrobe that reflects not just trends but my personality, values, and the joy of dressing up every day.
Want to try it yourself? Get 40% off your first month with Rent the Runway and see if it works for your next trip.
First time renting a wardrobe? Try these 14 Travel Fashion Hacks Using Rent the Runway: Tips for Stylish and Practical Packing
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