30 Shoes, Bags, and Jeans That Will Never Ever Go Out of Style
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 think we can all agree that these look wildly expensive.
The perfect pop of color that so many outfits will benefit from.
At this point, I'm convinced that flip-flops are here to stay.
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.
Tory Burch's Lee Radziwill bag designs just keep getting better.
Is a proud owner of this bag, I'll never stop carrying it.
JEANS
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.)
If you need new wide-leg jeans, this Toteme pair is worth the investment.
If your denim goals are casual and comfortable, this pair is for you.
Next up, 8 current trends our editors agree are worth it.
Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
Blake Lively, Sofia Richie, and More Stylish Women Know These Jeans Are Better Than Designer
They're $98 but look way pricier.
By Eliza Huber
-
Fashion People Swear By Khaite's Jeans—Now I Know Why
Signature silhouettes and striking details.
By Nikki Chwatt
-
It's Not a Coincidence—Everyone Is Trading Black Handbags for This Clashing Trend
Olivia Rodrigo included.
By Allyson Payer
-
Jennifer Lopez Just Wore the $98 Jeans the Internet Loves
She must've read the reviews.
By Allyson Payer
-
Fashion People in Paris Will Wear These 4 Elevated Basics With Jeans in 2025
Easy-to-style looks.
By Bobby Schuessler
-
I'm Clearing Out These Winter Trends and Buying These 7 Anti-Trend Alts Instead
This for that.
By Eliza Huber
-
J.Lo Carried a $10K+ Bag With the Anti-Trend Wardrobe Item I Never Spend More Than $100 On
*Never.*
By Eliza Huber
-
Sienna Miller Just Made Me Want to Wear the Jeans I Stopped Wearing Years Ago
If she wears them, they're still cool.
By Allyson Payer