The 5 Best and Worst Wardrobe Investments I’ve Made

And how to make the right decisions moving forward.
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It took me well into my 20s until I began to fully appreciate the concept behind quality versus quantity. Gone are the days where I'd return from the flea market with arm loads of vintage (read: mainly old, stained, hole-y) pieces that would collect dust in my drawers. My closet is no longer packed with a slew of going-out tops from fast-fashion stores that would disintegrate after one wear. I now aim to make much smarter purchases, grounded in classic silhouettes and neutral colors so I never tire of wearing them. I rounded up five of my all-time favorite purchases, as well as some of the other investments that didn't quite pan out (thank goodness for selling things via consignment):

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1. Gucci Loafers. I debated these loafers for about a year before I bit the bullet. I worried they'd come across as too preppy and make me look old fashioned, but they quickly became my most-used shoes. I love that they're easy to throw on and dress up jeans or cut-offs while adding just a touch of polish to any outfit. 

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2. Hermes Belt. I bought this as a 30th birthday gift to myself and it's my most beloved accessory (second to the chain-link bracelet I never take off that I inherited from my grandfather). It's not necessarily something I wear on a daily basis, but anytime I want to add a finishing touch to a dress or to cinch in a blouse, it always makes me feel put together (bonus: It's reversible, so it's almost like two belts in one)!

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3. Rag + Bone Poncho. A few years back, I passed by a woman sitting in First Class on the plane dressed in the chicest, most simple outfit. She had on skinny jeans, loafers, a thin sweater, an incredible poncho, and oversized sunglasses. I decided that I needed to seriously upgrade my travel uniform and invested in this Rag + Bone poncho as soon as I landed. It's camel-colored on one side and gray on the other, so I typically wear it on one side for one leg of the trip and switch it up on my way back. It feels like a luxurious blanket, but elevates my entire look, no matter what I'm wearing underneath.  

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4. Nili Lotan Trousers. When I saw these trousers on the hanger in a San Francisco boutique, I knew they'd be perfect, even without trying them on. I initially balked at the price tag, even though they were seriously discounted, and decided to try them on regardless. Turns out, they were even better than I'd imagined, hanging off my hips just enough to make them super flattering, with a slight drop crotch and subtle tapering to make them feel edgier than your traditional trouser. Plus, they look just as good with a crisp button-down and pumps as they do with a beat-up sweatshirt and sneakers.

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5. Burberry Trench (same designer here). This was my big purchase when we were on our Italian honeymoon and I've loved it ever since. Getting dressed for the rain is always kind of a bummer, but knowing that I have this to throw on always reassures me that whatever I wear, it will keep me dry while also looking my best. I went back and forth on the leather sleeves and while a classic trench would have worked, this piece feels unique and special and I love that it's a conversation-starter amongst strangers on the street.

Take-aways: While it's not ground-breaking, it's clear that my favorite pieces I own are all classic, neutral, and easy to wear. They're all pieces I can throw on in a variety of ways while also adding that finishing touch that takes each outfit to the next level.

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1. Christian Louboutin Peep-Toe Heels. These were the first designer shoes I ever owned, which G bought me for my birthday. I loved them so much and they were so elongating that I failed to realize that they were nearly impossible to walk in (and I can handle some pretty staggering heel heights). Of course that didn't stop me from wearing them all the time, though in retrospect, I should have gone with a slightly more modest heel that didn't nearly snap my legs in half. 

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2. Palm Tree Leather Skirt. I'm a sucker for an A-line leather mini skirt (my all-time favorite one from Zara is no longer available), so I assumed that this pale, palm-tree print version would only be an improvement on the classic. I wore it a couple of times to events, but because it was so recognizable, I found myself not reaching for it much beyond that, especially since it could really only be paired with the most basic of tops.

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3. Super Sunglasses. I still own and love these, but they are, hands down, the most uncomfortable sunglasses I've ever owned. The leather and gold detailing is so good, but because of all of that hardware, they're insanely heavy and hurt my nose anytime I have them on. I'll wear them for quick jaunts around town (key word: quick), but regret having invested in a pair of sunglasses that are this ill-fitting.

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4. Club Monaco Trousers. I live in high-waisted, wide-leg pants, so when I came across a pair in the prettiest pink, I figured they'd become a new wardrobe workhorse. I reach for them often, when it's chilly outside, but end up taking them off in favor of something a bit more neutral. While I'm certainly not averse to color, they're simply a lot less versatile than I'd hoped they'd be.

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5. Vince Leather Jacket. I bought this jacket back in 2010 and sold it a few years ago. I'd thought it would be one of those pieces I wore forever, but as it turns out, it never fit me perfectly. This one had side fabric paneling that I appreciated when I first got it, but over time, I found myself reaching for trench coats (classic) and varsity jackets (playful) instead of leather (a bit too rock-and-roll for me, apparently).

Take-aways: The most important thing I've come to realize about style is that you shouldn't venture too far from what makes you comfortable (both literally and figuratively). Whether that's in regards to a pair of shoes that you can barely walk in or a hard-to-wear printed leather skirt, stick to what you like best, especially when it comes to investing in big ticket items. I now also make sure to take my time before committing to something, really asking myself if it's something I can see myself wearing in 5, 10, 15 years.