When it comes to shopping, few things are more painful than spending a lot of money on something and rarely wearing it. I know that I've experienced this form of fashion pain on more than one occasion. I try to take my time contemplating big purchases such as designer shoes and only want to spend that much money on pairs that I'll wear over and over. And the good news is that designer shoes are made to last, so they could potentially be a part of your wardrobe and life for years to come.
So what makes a pair of shoes worthy of wearing over and over? The key is versatility potential. Are they in a color that goes with much of your wardrobe? Can you dress them up and down? Are they comfortable, and do they have a walkable heel height? Are they timeless enough to stay in style for multiple seasons to come? These are all great questions to ask yourself. And while it's all a bit subjective, I asked myself these questions while creating this designer-shoe list and found the answer to be "yes" on most counts.
Scroll to shop the chicest, most versatile designer shoes your hard-earned money can buy.
Khaite
Lorimer Metallic Crinkled-Leather Mary Jane Pumps
Sometimes, you just need metallic shoes. Let these be them.
Gucci
Leather Loafers
Gucci loafers are always the designer-flat-shoe goal.
Miu Miu
Bicolor Cap-Toe Mary Jane Pumps
Cap toes never go out of style.
Totême
The Riding Leather Knee Boots
Totême's riding boots are stunning and classic.
Loewe
Ballet Runner Nylon and Leather Sneakers
Everyone needs a good pair of dressy sneakers.
Saint Laurent
Le Loafer 15
I'm obsessed with these Saint Laurent loafers, and you will be too.
Prada
Logo Square Toe Bootie
These new Prada boots are pretty special.
Manolo Blahnik
Maysale 50 Buckled Suede Mules
These are the best kitten heels on the planet, which is why they're constantly selling out.
The Row
Ava Leather Mary Jane Flats
These perfect Mary Janes are a celebrity-favorite style.
Khaite
Dallas Short Western Booties
Fashion girls can't get enough of Khaite's understated Western boots.
Saint Laurent
West Chelsea Boots
Another pair of classic Western boots you can't go wrong with.
Manolo Blahnik
BB Pointed Toe Pump
No other pair of basic pumps will ever compare.
Saint Laurent
Blade Square Toe Slingback Sandals
These new Saint Laurent slingbacks are already going viral.
The Row
Canvas Platform Ankle Boots
This is one pair of chunky boots the fashion crowd will never tire of.
Jimmy Choo
Avenue 50 Leather Sandals
Every shoe collection needs a little color.
Bottega Veneta
Leather Mules
The chicest, most low-key designer wedges you'll ever encounter.
Christian Louboutin
Miss Jane 55 Patent-Leather Pumps
These may be new, but they're destined to become classics.
Chloé
Betty PVC Rain Boots
These will actually make you look forward to rainy days.
Prada
Soft Rain Boots
Another pair of rain boots that are making me feel things.
Golden Goose
Superstar Leather Sneakers
The most legendary designer sneakers of them all.
Gucci
GG Embellished Slingback Pumps
I will never get tired of looking at these.
Prada
Modellerie Mary Jane Pumps
The Prada triangle logo is basically investment-worthy insurance.
Adidas x Gucci
Gazelle Sneakers
This collaboration will never be forgotten.
Amina Muaddi
Felicia Slippers
The Amina Muaddi aesthetic remains near and dear to fashion people's hearts.
Manolo Blahnik
Hangisi 105 Embellished Satin Pumps
It didn't feel right not to include these.
Balenciaga
Cagole Leather Pumps
The Balenciaga Cagole trend is so massive, I don't see it going quietly into the night anytime soon.
Mansur Gavriel
Square Toe Ballerina Flats
I'm quite sure these lovely ballerinas will sell out soon, as they should.
The Row
Bare Satin Sandals
The OG strappy sandals that basically started the trend.
Loewe
Anagram Logo-Embellished Padded Leather Slippers
There will always be a place in this (fashion) world for cozy mules.
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 arts. 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.