I can say from experience that it feels great to spend your money on something you know you're going to wear constantly for years to come, as opposed to trendy items that could look dated sooner rather than later. When I was a younger, less experienced shopper, I learned this the hard way. The misconception about investment purchases is that they're expensive, but that doesn't always have to be the case. The unofficial definition of a sartorial investment buy is that it's a purchase that's money well spent because you wear it over and over.
Shoes, bags, and jeans are arguably the items we're most likely to wear countless times—if they're timeless, that is. So I compiled a very curated assortment of ten pieces from each category that will never go out of style (in my humble opinion, at least). These chic pieces will elevate your wardrobe for years to come.
Scroll to shop the shoes, bags, and jeans that you won't know how you lived without.
SHOES
I find kitten heel mules to be the most elegant shoes you can buy.
Saint Laurent's tribute sandals are here to stay.
These pretty much speak for themselves.
I think we can all agree that these look wildly expensive.
I had to show how pretty these look on the foot.
I'd be willing to bet that these are very comfortable.
The perfect pop of color that so many outfits will benefit from.
There's a reason these fly out of stock every summer.
At this point, I'm convinced that flip-flops are here to stay.
Even when ballet flats aren't so trendy, they're never really "out."
BAGS
Just a heads up—this quiet luxury It bag is selling out everywhere.
If I were in the market for a timeless investment bag right now, this is the one I'd choose.
Click through to see how perfect the size of this bag is.
Another quiet luxury bag you'll never want to part with.
You'll find yourself reaching for this versatile bag constantly.
This is still as coveted as when it was first released.
The perfect throw-it-all-in-and-go work bag.
Tory Burch's Lee Radziwill bag designs just keep getting better.
Is a proud owner of this bag, I'll never stop carrying it.
This bag has a cult following for
JEANS
These are the only light-wash jeans you need.
These Madewell jeans are some of the most comfortable ones I've tried.
Who What Wear editors have been raving about these for years. (Pro tip: Sizing up is recommended.)
Everyone needs a pair of white jeans and I highly recommend these.
Another pair of straight-leg jeans everyone loves.
These might be the best under-$100 jeans money can buy.
If you need new wide-leg jeans, this Toteme pair is worth the investment.
Every denim collection needs at least one pair of flares.
If your denim goals are casual and comfortable, this pair is for you.
Our editor Judith swears by these classic trouser jeans.
Next up, 8 current trends our editors agree are worth it.
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You're 100% a Fashion Person If You're Styling Your Jeans in This Chic Way for Fall 2025A game-changing styling trick.
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By October, You'll Understand Why This Specific Bag Trend Is So Popular Among Fashion People Who "Get It"Andy Sachs gets it.
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Cooler Than a White Button-Down: This Specific Shirt Color Is the Key to Looking Chic This FallIt's all over the streets and the spring/summer 2026 runways.
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Fashion People Are Reaching For Little Beaded Bags Right Now—31 Chic Styles That Have My AttentionFrom Zara to Fendi.
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Spotted on Kendall and Hailey: The Pant Color Trend People Are Swapping Blue Jeans ForIt girls with good taste know best.
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Cool It On the Skinny Jeans—Chic People Are Wearing These 6 Fall Denim Trends InsteadAre you taking notes?
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Jeans, Flats, Jackets, and Sweaters—The Best of the Best In Each Category For FallMeet your new hero pieces.
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Hold the Light-Blue Jeans—People in Paris Know This Denim Trend Is Far Superior for FallIt's so elegant.
