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.
-
Simone Ashley Is in the Fast LaneSince her breakout role in Bridgerton, our Spring Issue cover star has quickly risen to A-list status. Up next, she masters the rom-com leading lady.
-
The Spring 2025 Shopping Guide: Where to Buy the Biggest Trends of the SeasonYour short list of the season's key buys.
-
Madewell's Insiders Event Sale Is So Good—27 Picks Chic People Will Be Adding to Their CartsGet 25% off just about everything.
-
This Just In: Plushies Are the Freakier Trend Gen Z Is Dumping Bag Charms ForHot take: I'm obsessed.
-
These Are the 7 Stylish Shoe Trends Fashion People Will Be Wearing With Jeans This SpringI see chic denim outfits in your future.
-
If You Have Great Taste, You Don't Want to Miss These 30 Chic J.Crew and Madewell Sale PicksSo many gems. So little time.
-
Wait—Did Elsa Hosk Just Intro the New It Bag of 2025?One word: Prada.
-
I Hate to Admit It, But After Purging My Closet, I Had to Rebuy These 8 Hero PiecesHere's what I learned after my closet identity crisis.
-
Cameron Diaz Just Wore the Timeless Bag Trend That Makes Every Outfit Look AffluentThat's the goal, right?
-
Gigi Hadid Just Made Mom Jeans Look Brand-New Again in ParisIf anyone can, she can.
