The 20 Most Timeless Designer Bags and Shoes

If your idea of a shopping nightmare is investing in a designer bag or pair of shoes only to see said item become oversaturated and no longer be “cool”, you’ve come to the right piece of content. Designer items are more expensive than ever (a lot more expensive, I might add), so, understandably, they’re purchases that most don’t take lightly. Speaking for myself, I can be a bit impulsive, but not when it comes to luxury items. I think about those long and hard. And the most important criterion that I consider is how timeless my potential purchases are.

If you’re thinking of making a new designer bag or shoe purchase, I’m here to offer a little assistance. I’m highlighting ten bags and ten pairs of shoes that are timeless enough to get years of wear. Keep scrolling to prep yourself for a smart luxury purchase (and shop the timeless options if you’re ready).

The Shoes

Manolo Blahnik Maysale Mules

Manolo Blahnik’s Maysale Mules have been around since 1991, which is a long time for a shoe to be popular. It’s a testament to how timeless and elegant these heels are. They come in several heel heights but I’m partial to the kitten heels.

Gucci Jordaan Loafers

Even though Gucci’s Jordaan Loafers have significantly crept up in price over the years, I still think that they’re worth it. I’ve owned mine for probably seven years and they still look chic and elevated—even when they’re a little beat up. Plus, you won’t find a more comfortable pair of loafers.

Saint Laurent Tribute Sandals

Saint Laurent’s Tribute Sandals have sparked a million imitators, but none compare to the quality of the originals. Next to Hermès Oran Sandals, they’ll forever be the ultimate vacation sandals.

Miu Miu Ballerinas

Miu Miu Ballerinas haven’t been around quite as long as some of the other styles on this list, but they’re well on their way to becoming classics as well. Miu Miu continue to release the instantly recognizable flats in new iterations, with my current favorite being crochet.

Chanel Slingback Pumps

There are several iconic Chanel shoes that could’ve made this list, but the Slingback Pumps get my vote. They make every single outfit look more elegant and are surprisingly comfortable.

The Row Bare Sandals

There may be newer, trendier The Row shoes out there, but the minimal, versatile Bare Sandals are as good as it gets. You’ll never be scrambling to find a pair of shoes to wear to a wedding or date again—these are it.

Jimmy Choo Romy Pumps

More often than not, when a celebrity wears a pair of pumps on the red carpet it’s Jimmy Choo’s Romy Pumps. They’re as classic and flattering as it gets.

Khaite Dallas Boots

Few things in life are guaranteed but something that is is that whenever Khaite Dallas Boots restock, they will sell out. They’ve shown just how chic Western wear can be—even before Beyoncé did.

Toteme Leather Flip-Flops

Toteme’s kitten-heel flip-flops are incredibly simple, and that’s why fashion people love them. They add a certain cool factor to summer outfits with minimal effort.

Maison Margiela Tabi Ballerinas

Without a doubt the cool-girls ballet flats, Maison Margiela Tabis have a cult following that rivals all the other ballet flats on the market. They’re a bit off-kilter, and that’s what we all love about them. Don’t sleep on the new satin iteration.

The Bags

Gucci Jackie Bag

Gucci’s re-invention of popular bags from is archives continues to pay off, with the Jackie Bag being an instant hit. The timeless shoulder bag has countless celebrity fans.

Loewe Puzzle Bag

Loewe’s Puzzle Bag was an instant hit that’s remained popular year after year. It’s spawned many off-shoots, including the sought-after Puzzle Fold Tote. You can be confident with your choice to purchase one as it’s a timeless option that’s perfect for day or night.

The Row Half Moon Bag

The Row’s It bags are always nearly impossible to find in stock (ahem, The Margaux), including ones that came out years ago. One of those is the Half Moon Bag, which first graced us with its presence in 2014. The subtly luxurious shoulder bag is one you’ll continue to reach for year after year.

Bottega Veneta Andiamo Bag

Never has the fashion world loved a logo-less bag more than Bottega Veneta’s Andiamo Bag. The braided tote with its subtle signature hardware look incredibly luxurious.

Prada Galleria Bag

It’s rare to meet a Prada bag that isn’t utter perfection, but some are more timeless than others. If it’s longevity you’re seeking, you can’t go wrong with the Galleria Bag. The structured satchel is as elegant and practical as it gets.

Chanel Flap Bag

It’s safe to say that every luxury handbag collector has at least one Chanel Flap Bag in their collection. It’s the most iconic, coveted, and recognizable designer bag on the planet.

Khaite Lotus Bag

Khaite’s Lotus Bag is the ultimate throw-it-all-in-and-go bag. I’m partial to the mini size, which still holds a ton despite its small size.

Saint Laurent Le 5 à 7 Shoulder Bag

Saint Laurent Le 5 à 7 Shoulder Bag hasn’t been around for all that long, but I think it’s a instant classic. It’s the perfect option if you want an understated logo bag. Celebs like Taylor Swift and Hailey Bieber count themselves as fans.