The Closet Confessional: 5 Investment Pieces I'd Buy Again, and 3 I Regret

An honest cost-per-wear review of the designer pieces in my wardrobe.

I’ve been doing a closet inventory the past few weeks, and the math surprised me. The pieces sorted themselves into two clear piles: the ones I reach for without thinking, and the ones I walk past every morning and quietly pretend not to see.

I usually share what I love, but this one called for honesty about what I don’t. Five pieces I’d buy again tomorrow, three I genuinely wish I hadn’t, and the three questions I now ask before any investment purchase.

Let’s start with the wins.

---

The 5 Wins: cost-per-wear math & the real reason each one earned its keep

1. Bottega Veneta Teen Jodie

I bought this in 2022 and have reached for it almost daily ever since. It’s the bag I recommend more than any other when readers ask me where to start with a real investment piece.

A few things make it work. The size is the sweet spot, small enough to feel polished day to night, big enough to actually hold my essentials (phone, wallet, keys, lip, sunglasses) without looking stuffed. The black goes with everything in my wardrobe, which is the whole point of an investment bag. And it’s broken in beautifully; the leather has softened in a way that only happens with the really good stuff.

A couple of things I didn’t expect when I bought it: it lays completely flat, which makes it a dream to pack for travel. And the quiet luxury look has aged better than I could’ve predicted. No logos, no obvious branding, just the recognizable intrecciato weave for anyone who knows. It reads expensive without trying.

This is also the bag that taught me the lesson in the regret section below. I loved it so much I bought it in a second color, and the second color barely got used. The original black was the win. It always is.

The cost-per-wear math on this one stopped making sense to track years ago.

2. Chanel Ballerinas

I own seven pairs now, I know.

This is the rare exception to the rule I laid out in the regret section below, the one piece in my closet where buying it in multiple colors and materials has actually worked. I wear them all. The classic beige with the black toe gets the most rotation by a landslide because it’s the most neutral and goes with everything in my wardrobe, but the more fashion-forward pairs earn their keep too. That’s where the fun lives.

Here’s what makes them worth it: they are, hands down, the most comfortable pair of shoes I own. I’ve worn them on long-haul travel days and walked through New York City for ten-plus hours in them with zero regret, which is genuinely something I can’t say about any other designer shoe in my closet. The construction holds up trip after trip, the leather softens in all the right places, and they manage to look polished even after being put through it.

If I’m being honest, this is the one place in my wardrobe where I let the collector instinct off the leash. Every other category, I edit ruthlessly. With these, I just keep finding new ways to justify the next pair. And so far, every single one has earned its closet space.

3. Vintage Cartier Tank Française Watch

A small caveat on this one: it was a gift from my husband. But it earns a spot on this list because it’s still an investment and one I had a clear vision for long before it came home to me.

I’d been searching for the right everyday watch for years. I knew exactly what I wanted: something dainty enough to wear like jewelry, polished enough to take from a morning coffee run to a dinner out, and timeless enough that I’d never need to replace it. The Tank Française checked every box. And the fact that we tracked down a vintage piece, a model that isn’t made anymore, turned a beautiful gift into one with a story.

What I love most is that it reads as a piece of fine jewelry, which means I actually wear it every day instead of saving it for occasions. It layers under a sleeve in winter and stands alone with bare wrists in summer. The proportions are exactly right with a smaller frame. And vintage Cartier has a patina you simply can’t fake on something brand new.

This is one of those pieces where the “investment” math isn’t even about cost-per-wear, it’s about the fact that I’ll still be wearing this in twenty years, and probably handing it down after that.

4. Khaite Leather Belt

The piece to instantly elevate the most basic outfit. Jeans and a tee become an outfit. And dressed up, it does double duty as a piece of jewelry, the kind of detail that makes people ask where you got it.

This is the case I’d make for any of my investment belts, honestly. (I could write a whole post on belts alone, let me know if that’s something you’d want). But the Khaite Benny is the most classic of the bunch, and the most universally wearable. Like the Bottega, it works with nearly every outfit in my closet. It adds without distracting. It elevates without overwhelming. And after well over a hundred wears, the leather still looks as good as the day I bought it.

The cost-per-wear is measured in cents at this point. It transitions through every season. There’s no version of my wardrobe that doesn’t need this belt.

If anyone’s still skeptical that an accessory can be an investment piece, this is the one I’d hand them.

5. Vintage Hermès Kelly

This is the one. If I could only keep one bag from my entire collection, it would be this Kelly.

I bought it second-hand for my 40th birthday and the part that makes it mean even more is that it’s from the same decade I was born in. There’s something about carrying a bag that’s lived a whole life before me, made in the era I came into the world, that no new bag could ever replicate. It felt like the right marker for a milestone birthday: not just a beautiful object, but one with a history that mirrors mine.

The Kelly itself doesn’t need much of a sell. The shape is the most timeless silhouette in luxury handbags. It has been carried by every kind of woman for nearly a century and will look exactly as right in another forty years. Black makes it endlessly wearable. Vintage makes it singular. And the secondhand market actually made it more attainable than buying new, which is a quiet luxury truth more women should know.

This is the bag I’ll pass down. That’s the highest compliment I can give a piece in my closet.

---

The 3 regrets: pieces I romanticized, why they didn’t deliver, what I’d buy instead

1. Cartier Juste Un Clou Bracelet, Small Model

I bought this in 2020 as a milestone marker for my business, something I’d always wanted, and a way to commemorate a year that felt earned. I loved the idea of it sliding into my growing stack.

It took only a few months of wear to realize I actually disliked it. The small model felt flimsy in a way I wasn’t expecting at that price point, the nail caught on everything and bent out of shape constantly. I took it to the Cartier store within the first year to have it repaired, which should’ve been my sign.

Then in 2023, on the way home from a trip to Europe, I’d gotten into a rhythm of taking my jewelry off at security. By the time I landed at LGA, muscle memory took over, I dropped it in the TSA bin and didn’t realize until I was long gone. Just like that, it was over.

I’ve thought about replacing it more times than I’d like to admit. But every time I get close, I remember how much it actually bothered me to wear. I’ve tried the classic size and it’s just too big on my wrist, so I’m stuck in the middle.

Dear Cartier: please make the small model with the same construction as the classic. I’ll be first in line.

2. Buying the Same Handbag in a Second Color

This one isn’t a single regret, it’s a pattern I’ve finally caught myself in.

It happens like this: I invest in a handbag, fall hard for it, and wear it nearly every day for months. Then comes the logic that’s gotten me every time; “I love this bag so much, I should get it in another color.” So I do. And every single time, the second color sits in my closet barely touched. A few wears in, max. Eventually I end up reselling it on the secondary market, usually at a loss. (I did this with my Bottega Teen Jodie, Toteme T-Lock bag, The Row Totes, & Celine Belt bags).

What I’ve learned: the bag I’m reaching for every day isn’t actually the style, it’s the specific bag. The leather that’s broken in just right, the color that goes with everything in my wardrobe, the one I trust. A second color doesn’t double the use; it splits it, and one always wins.

The only exception I’d make to this rule is an Hermès Birkin or Kelly. The shape is so classic and the investment so real that owning multiples in different colors actually makes sense; those are the only bags I’ve consistently worn in the same style across colors without one falling out of rotation.

The lesson: if you find yourself reaching for the same bag every day, that’s the win. Resist the urge to “expand the collection.” Buy a different style next, not a different color of the same one.

3. Trendy Designer Shoes

You know the ones, the it shoe of the moment, the pair every girl is wearing, the style that’s all over your feed for six weeks straight. I’ve bought a few of those over the years, and almost without fail, I wear them once and then they collect dust on the shelf.

Sometimes the style is too specific to pair with anything beyond the one outfit I bought them for. Sometimes the fit isn’t quite right but I overlook it because I want to make it work. And sometimes the moment just passes, what felt fresh in March feels dated by September, and you can’t unsee it. The cost-per-wear math is brutal.

What I’ve come to learn: trends are fun, but they’re not where the investment dollars belong. I’d much rather spend a little on something fashion-forward from a contemporary brand and save the real money for classic styles that will quietly carry me for the next decade; a great loafer, a perfect black pump, the right pair of ballet flats. Those are the shoes I reach for hundreds of times. The trendy designer pair? It’s still sitting there, tags-off and barely worn, looking expensive and unloved.

The lesson: when something is having “a moment,” that’s almost always the wrong time to spend designer money on it. Buy the trend cheap. Save the splurge for the forever pieces.

---

Before You Buy: 3 Questions That Could’ve Saved Me From Every Regret on This List

1. Would I still want this if no one else were buying it right now?

This is the trend filter. The Juste un Clou was everywhere when I bought it. The trendy designer shoes were the “it” pair of the season. When something is having a cultural moment, it’s almost impossible to separate genuine desire from the noise around it. If you’d still want the piece in a quiet room with no algorithm, no Reels, no friend group buzz, that’s real. If you’re not sure, wait six months. The pieces that survive that wait are the ones worth your money.

2. Does it work with at least five things I already own?

Investment pieces have to earn their keep through versatility. The Bottega Teen Jodie goes with everything in my closet and that’s why it’s been in daily rotation for years. The trendy shoes paired with exactly one outfit. If you’re already mentally building the wardrobe around a single piece before you’ve bought it, that’s a flag. Great investments slot into the life you already have. They don’t require you to build a new one.

3. Can I picture myself still wearing this in ten years?

The Kelly will outlive me. The Tank Française will get handed down. The Chanel flats are on their seventh pair and going strong. The pieces I regret? I couldn’t have honestly answered yes to this question at the time but I just didn’t want to ask it. If the answer feels like a stretch, you’re not buying an investment. You’re buying a trend with a luxury price tag, and that’s the most expensive kind of purchase you can make.

“What’s the piece you wish you’d never bought? Hit reply I read every one.”

---

xx,

Amy