There's a time to shop for trending items—aka pieces that will only really work in your wardrobe for a season or two—and a time to invest in timeless, forever staples. A party with a very specific dress code or theme falls into the former category, while a designer handbag or pair of classic jeans would go in the latter. If what you're buying has a short shelf life, don't spend real money on it. What's the point if it'll become useless in a few months?
So, when it comes time to introduce pieces to your wardrobe that you plan to still own and wear one, two, or even 10 years from now, that's when it's smart to devote a significant chunk of change to your purchases. It's all about price per wear, and donning something multiple times a year for many years will essentially make even your biggest buys free. (Girl math?)
To help you decide what you want to spend your hard-earned money on, I went ahead and rounded up 36 timeless investment fashion items that I guarantee will continue to get regular wear for at least the next decade. There are designer-brand icons, like the Dior Bar Jacket, The Row Margaux bag, and Cartier Tank watch, as well as new arrivals that I'm predicting will reach cult status with time, like Tory Burch's new large Lee Radziwill shoulder bag and Khaite's Winslow jeans. Intrigued? Keep scrolling.
Yes, this bag is in stock… for now.
I know every brand is making this pants style right now, but none will compare to the OG High Sport pair.
Everyone has that one pair of ballet flats they love and wear on repeat. For me, it's Margaux's Demi Flats.
If I were to invest in one fall outerwear piece in 2025, it would be this suede bomber jacket from Saint Laurent. Easy.
A beautiful slip skirt that'll never go out of style.
This is the kind of dress you end up wearing once a week for, well, life.
This navy pair of Prada sneakers is both deeply cool right now and extremely neutral, making them an instant classic.
No one's ever regretted buying a Cartier Tank. Period.
You really can't go wrong with a Burberry trench coat.
The fit and wash on these will always be in style.
Buy these if you want to feel like you're always at a luxury hotel.
My social media feeds are losing it over this bag. It's already set to become a long-term fan favorite.
When an item is both practical and chic, it probably will outlive the trend cycle.
Just a great forever belt.
The perfect not-too-baggy-but-not-too-tight jeans.
I low-key drooled over these when I first saw them. They're gorgeous and will work with dresses, jeans, skirts, and more.
A Dior Bar Jacket is probably the fashion item I want most.
This tank top does not stretch out, like, ever. I don't know how Tibi did it, but it's a modern fashion miracle.
I plan to buy these and wear them every single day. Who needs multiple pairs of sunglasses when the one pair you own is this chic?
It gets hot every summer. You might as well buy a great pair of pants that can help keep you cool now, and just keep wearing them summer after summer.
For pairing with a white T-shirt or a cocktail dress.
The fact that this coat is on sale right now feels crazy to me. Pieces this good, in my mind, should never be marked down (though I'm not complaining).
The only kitten heels a girl could ever need.
Just easy.
There are shockingly a ton of Margaux bags available on The Row's website right now. Don't let this opportunity slip away.
I have the blazer version of this coat and get so many compliments on it. I've probably worn it at least 30 times, too.
This is the kind of necklace you throw on with a T-shirt and jeans, and suddenly, your outfit feels special.
Great tank tops deserve to be worn for years and years on a regular basis.
The perfect flight-to-dinner pants.
Jacques Marie Mage is the epitome of luxury eyewear.
You can wear this suit as a swimsuit or a bodysuit. The options are endless.
I like to keep shirts like this hanging on my bedroom door so I can throw one on whenever I can't figure out what to wear.
A no-frills belt you'll still own in 2030 and beyond.
Owning one great leather skirt will work wonders for your wardrobe. This one's color makes it feel even more buy-worthy.
Rubber flip-flops won't last. This leather pair will.
Prepare for this durable travel trunk to accompany you on every long trip for the rest of your life.
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