Vacation

I Always Shop Before Traveling—These 21 Items Are My Most Successful Purchases

Allyson Payer  Tue, 12 Apr 2022  Who What Wear

I suppose it's a little counterintuitive to admit this right now, but I actually don't think the best time to shop is before taking a trip. I've made plenty of shopping mistakes when last-minute panic buying for a vacation or work trip, and I constantly vow to never do it again. But on the flip side, many of those panic buys have been surprisingly successful. Those are the ones I'm here to talk about.

I always make a pretty detailed packing list when I'm preparing for a trip, even planning out which accessories I'm going to wear with which outfit. It's the only way I can seem to manage to not overpack (or under-pack). I often wait until the last minute to make this list (not recommended), and that's when I realize I'm lacking some of the things I need (well, want) to complete some of the outfits. Hence the panic-buying. And while I'm not encouraging this method, here are the TK times it actually worked out for me, along with some photos of my travel style, just for fun. Scroll to shop my travel shopping success stories.

This easy shirt can be worn on the plane, as a swimsuit cover-up, with a miniskirt—and so many more ways.

These perfect jeans are soft, comfortable, and flattering—all the things I want in travel pants.

This two-tone cardigan hardly takes up any room and it works both day and night.

This ended up being the perfect summer travel bag. Unlike a lot of other raffia totes, it's on the small side, but it still fits everything I need and more.

These are the perfect denim shorts—you can quote me.

I love a vacation hat.

I ordered this pretty swimsuit for a trip to Miami last summer.

These non-bulky, lightweight sneakers make great travel shoes.

I'm constantly getting compliments on this cardigan.

I recently got these perfect black pants and have been telling everyone to buy them.

I love wearing this cool sweatshirt on flights—it's incredibly soft.

Speaking of comfortable, if you have a long flight, take my advice and order these leggings for it.

I wish I could impress you by telling you how many times I've worn these perfect sandals, but I lost count a long time ago.

I have a bit of a baseball cap problem (as in, I keep buying them), but this one is the one I wear the most. I guess I knew that would be the case when I panic-bought it. It's a splurge but I think I've gotten my money's worth.

To be honest, I already owned a pair of Arizona sandals when I ordered these, but the soft footbed aspect convinced me I needed these for a trip I knew I'd be walking a lot during.

This lightweight Prada bag is perfect for squeezing into a suitcase, and I love that I don't have to worry about it too much if it rains or snows.

One of my favorite ways to dress up an outfit for a night out is with fancy earrings. Completedworks makes some of my favorites. I bought a pair before a trip to L.A. last December and have worn them many times since.

What can I say—I love a hat. This is the one I always bring to NYC in the winter.

I brought this jacket (in navy) to D.C. last spring and it was perfect for the weather. 

Logo socks don't take up a lot of room, but they do add a lot to an outfit.

Next up, shop the knit tops I'm debating buying for summer (starting at $18).