The Top 5 Best (and Worst) Wardrobe Investments I’ve Ever Made

Here’s what we can learn from our greatest wardrobe victories and mistakes.
Pictured: VETTA Cropped Mockneck Sweater, J Brand Liza Mid-Rise Culotte Jeans and Everlane Day Boots.
Pictured: VETTA Cropped Mockneck Sweater, J Brand Liza Mid-Rise Culotte Jeans and Everlane Day Boots.

They say that hindsight is 20/20 and that couldn’t ring truer when it comes to the items we choose to buy.

Maybe you finally decided to splurge on those designer heels you’ve been lusting after, only to find out that they kill your feet. Or perhaps you snatched up a pair of those retro, narrow cat eye sunglasses that everyone was wearing this past summer – and then immediately felt that pang of regret when you realized you don’t really feel like you when you wear them.

Whatever that bad investment was, it’s come back to haunt you and you’re wishing you could go back in time to tell yourself to put your wallet away and save your pennies for something better.

There have been many times when I wish I could have had that conversation with myself.

But since I don’t own a time machine, I’ll look back at the good, the bad and the downright silly purchases I’ve made over the years, and this will hopefully be an opportunity to learn from my victories and my mistakes.

Here are the top 5 best and worst clothing investments I’ve made and the lessons I’ve learned from them.

The Winners

1. Everlane Denim Jacket

I had to rack my brains a little to come up with my top 5 best wardrobe investments of all time, but this one was a no-brainer. I had been on the lookout for the perfect denim jacket for years, but everything I found was either too distressed, too embellished, too oversized or too cropped. I was like Goldilocks, lost in a sea of denim.

I finally found my dream denim jacket on Everlane’s website. It’s the perfect light blue wash and the fit is oversized enough to layer a light sweater underneath, but not so large that my petite 5’2’’ frame is swimming in fabric.

I’ve worn it casually with a t-shirt and some culottes on weekends and I’ve dressed it up and paired it with a jumpsuit and strappy heels for more special occasions.

2. Sparkle & Fade Gray Blazer

I’ve had this blazer for so long, I can’t even remember when I first purchased it. I have a faint memory of discovering this gem in an Urban Outfitters sale back in my college days, which means I’ve had it for at least seven years.

I had no idea it would play such an important role in my wardrobe. I’ve worn it to job interviews, work conferences, happy hours and family dinners. It actually gets a lot more wear than my black blazer.

I like how the cotton material dresses it down a tad and the light gray color keeps it from looking too much like a full-blown suit when I wear it with black dress pants. I find the combination of a black blazer and black dress pants to be slightly too formal and stiff, so this is a good alternative.

If I had to guess, I would estimate that I’ve gotten at least 100 wears out of this blazer. Not bad, considering I got it on sale for less than $40.

3. Everlane Day Boots

Alright, so I haven’t had these in my collection for very long. Everlane just launched the Day Boots in September, but they’ve been consistently making their way into my regular rotation, week after week.

I recently had to retire my old Chelsea boots because the leather was literally cracking and the soles were pretty much destroyed (RIP). I bought the Everlane Day Boots to replace them.

I was scared of the price tag and nearly changed my mind at the last second when I brought them up to the register, but I’m so happy I bit the bullet.

They’re insanely comfortable. I’ve worn them all day, walking up and down the hills of San Francisco, and they passed the comfort test. My feet were still completely blister-free by the end of the day.

I love that they’re a classic and unassuming style with an elegant, flattering silhouette. I have a feeling these will continue to be a favorite for many years to come.

4. Daniel Rainn Utility Jacket

I’ve had this jacket for so many years and I’ve worn it countless times. If I were to deem any item in my wardrobe as my “old reliable,” this jacket would be it. I’ve worn it to music festivals, picnics in the park and weekends in the city.

I think I picked it up from Nordstrom Rack or TJ Maxx several years ago. The lining is extra soft and it’s thick and warm without being too restrictive.

This is one of those pieces that you don’t even have to think about, and that’s exactly what I love about it.

5. Lou & Grey Open Cardigan

This cardigan is extra special because it actually used to belong to my friend, Katie Tingley, who is also a guest contributor to The Minimalist Wardrobe. I was in the market for a new sweater, and when I saw this one listed on her Poshmark, I immediately fell in love with how soft and cozy it looked.

I think it’s safe to say that I’ve worn this cardigan at least once per week since I’ve gotten it. Plus, it’s fun to inherit clothes from someone you know and I love that I’m able to give her garment a second life.

The Regrets

1. All Saints Leather Jacket

I’d been wanting an All Saints leather jacket for years, so I’m pretty sad that I had to put this one on the “naughty list.”

I found an All Saints Belvedere jacket on Poshmark listed at a fraction of the original price. An All Saints jacket can range from $450 up to $1,400, and I snagged this one for $230. I bided my time on this one because $230 is obviously still a large sum of money for a single item.

But I couldn’t get this jacket out of my head and was stalking it on Poshmark, eBay and any other site I could find it on for months. When the seller offered a private discount, I couldn’t resist temptation any longer.

While the condition of the jacket is excellent, it has a weird smell that’s not necessarily bad, but doesn’t quite make me want to wear it as much as I should.

It’s also a size 0 and All Saints sizing runs extremely small, so it’s a tad snug in the shoulders and difficult to layer with chunky knit sweaters.

I wouldn’t say that this purchase was a complete flop, but if I had to do it all over again, I’d wait to invest in my dream leather jacket that fits me perfectly, even if it ended up costing me a little more.

2. Paige Denim Jeans

I bought a pair of flared Paige jeans from TJ Maxx back in college. And I’m not going to lie, the main reason why I bought them is because they’re designer and they were on sale.

I couldn’t pass up that kind of a deal and so I bought them, even though the style was dated and not something that felt like me. I figured I could get them tailored to fit more like a straight leg pair of jeans.

But you know what? It took me five years to bring them to a tailor! Yes, five years. It’s embarrassing for me to admit, but it just goes to show that if you don’t love an item enough to bring it in to the tailor right away, it’s probably not worth it.

These jeans are currently in my “to sell” pile.

3. Anthropologie Lace Dress

I still love the look of this dress. It’s just so pretty and whimsical.

But in the three years since it’s been hanging in my closet, I haven’t worn it once – which is such a shame.

I thought it would be the perfect semi-formal dress to wear to weddings, but the nude-colored panel underneath is just a little too close to my skin tone and makes it look inappropriate for wedding attire, if you know what I mean.

I’m still having trouble letting go of this dress though and am determined to make it work.

4. Forever 21 Overalls

I bought these on Poshmark on a whim. You know the kind. When it’s late at night and you’re feeling like you have some money that’s burning a hole in your pocket and you just want to BUY SOMETHING. That was me.

This was obviously a trendy piece. I thought overalls looked so cute on some of the influencers I follow on Instagram and I wanted to recreate that same effortless, artsy look.

But given the number of times I’ve worn these overalls, I’m not sure they were a smart purchase. This was clearly an impulse buy.

5. Diane von Furstenberg Silk Cami

I bought this gorgeous midnight blue silk camisole on Poshmark for just $18. It’s in lovely condition, but I just don’t wear it.

It sort of looks a little too much like lingerie or fancy PJs with the black lace trim. And even though I envisioned myself channeling this ultra-cool Parisian girl vibe and pairing it with a black blazer, dark denim jeans, a pair of heels and red lipstick on a night out, I haven’t worn it once. Probably because I never go out anymore.

This was another case of me trying to be someone else and discovering that it just doesn’t work.

Conclusion

After doing some reflecting on my best and worst wardrobe investments, a few things became clear to me.

The first is that I’m a big fan of outerwear. This isn’t a huge surprise to me since jackets, cardigans and coats are some of my favorite garments to buy, but it’s good to know that these pieces actually get a lot of use in my wardrobe.

The second thing I learned is that I tend to lean toward more casual, relaxed pieces vs. dressy ones. Give me a cozy cardigan over a cocktail dress any day.

The third thing I learned about my personal style is that fit is a big factor in what I choose to wear on a daily basis. If I don’t feel 100% comfortable in what I’m wearing, then it’s not going to work out.

Lastly, I’m a sucker for a good deal, which I’ve always known.

But what I’m learning now is that it’s better to invest in higher-quality pieces that I absolutely love. Oftentimes, that comes with a higher price tag, but if you wear it over and over again, then it’s absolutely worth it.

Which items would make your list of best and worst wardrobe investments? Let me know in the comments below!

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