People Are Shocked to Know I Thrifted These Outfits From Goodwill

Welcome to Goodwill Hunting (like the movie, except not at all), a series in which our assistant editor Anna LaPlaca takes you through all the fashion finds she's unearthed from secondhand stores. Whether she's scouring her local Goodwill or flipping through racks of curated vintage, she never fails to find pre-loved items with a lot of potential to look brand new again.

Greetings, fellow thrifters! If you're not familiar with the Goodwill Hunting concept, here's the rundown: I thrift-shop like it's my job, and in the process, I've uncovered some pretty savvy and accidentally on-trend finds. (See the square-toe boots below.) Here's where I share all my best thrift store finds of the moment and show you how I'm incorporating each of them into my regular outfit rotation.

Why do I thrift, you ask? These days, a certain vintage aesthetic is trending, which means it's not hard to create a really cool outfit with clothing that has lived a previous life. It also means that if you know which nostalgic trends are coming back around, as you probably do being a Who What Wear reader, you'll be able to find the authentic versions of the '80s, '90s, and '00s trends that all the new brands are currently selling.

That said, I'm sharing my most recent winter thrift store finds with you below. From a pair of checkered trousers that go with everything to a boxy blazer I transformed by taking it to the tailor, keep reading to see how I've styled each piece and then shop all the other pieces I wore with them.

The Items: Cropped Blazer and Square-Toe Boots

First off is this pinstripe blazer that was way oversize when I first found it. I like the shape and print, though, so I had it tailored into a cropped blazer. My tailor may have given me a confused look when I asked that it be taken way up, but I'm so pleased with the way it turned out. The strong-shouldered jacket gives off an '80s feel which I'm very into.

Now I'd like to direct your attention to my boots: a pair of aggressively square-toe ankle boots that are indeed a Nine West creation (I'm betting from the '90s). I picked them up long before the square-toe shoe trend really took hold, but now that it's a thing I've been wearing them nonstop. A case in point that everything comes back around again!

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The Item: High-Waisted "Grandpa" Trousers

When I found these high-waisted wide-leg trousers, they reminded me of the kind my grandpa would wear (grandpa dressing, I swear it's a thing). Some of the best trousers I own are actually from the men's section since I find they have a better shape to them and are always perfectly high-waisted on me. To give them a more ladylike spin, I styled them with white pumps, a top-handle bag, and a fun leopard-print top.

Here's a close-up of the trousers. They're a rich chestnut color with an ever-so-faint checkered print.

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The Item: Oversized Crewneck Sweatshirt

I've found that some of the softest graphic tees and sweatshirts I've ever come across were vintage rather than new. There's something about the pre-worn quality that gives these basic pieces some character, though there are also ways you can wash store-bought clothes to give them the same feel. This $19 vintage wash is a start.

Mine is an oversize navy crewneck sweatshirt with the faintest paint splatters that I was actually quite pleased to find out didn't come out in the wash. (Again, I think it gives the piece more character.) It's a simple item, really, but reminds me of the kind that Princess Diana would always wear with her bike shorts (another look I'm game to try). I've taken to layering it over a thin turtleneck for some added dimension. Here, I'm also wearing it with ankle socks and loafers to play up the sweatshirt's preppy feel.

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Speaking of affordable ways to nail current trends, here's how to shop every major spring trend from Amazon for under $100.