The Wardrobe Staple I Learned to Love Over Time

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In my early to mid twenties, I was mostly a boots-only person. Whether I was headed to the office, a night out with friends, a weekend stroll, a grocery store trip, you could find me in a pair of heeled ankle boots. But after a few years of running around the city with an extra 2 inches under my feet, I craved something a little easier to get around in, something I could wear all day without exhaustion, something well, flatter. 

I had avoided flat shoes for a few reasons, but mainly because I am relatively petite. Standing only 5 foot 3 inches tall, I liked the way I looked with some extra height, and I adjusted my outfit silhouettes accordingly. In the early stages of my career working in the Vogue accessories department, I became familiar with a lot of footwear, and I mean a lot. A classic penny loafer was always on hand in a range of sizes in case stylists needed a pair or two for upcoming shoots. A few of my colleagues dashed around the office in similar pairs. Inspired, I decided I wanted to try one out in hopes it could work for me, as well.

I decided I’d try an inexpensive pair out first, in case I didn’t like them. The first loafer I bought myself was a shiny, slightly grungy pair from Zara. Despite wanting to make them work, I still wasn’t totally sold. I had trouble wearing them with my floor-grazing trousers, but realized I loved how they looked with cropped, flared pants or jeans and socks. After a little trial and error, I welcomed the flat loafer into my wardrobe and I decided it was time I upgraded my training wheels pair for something more legit.

Photo Courtesy of Madeline Fass

I traded in my plastic Zara’s for a beautiful, classic style from Scarosso. Later that year, I found a very marked down Loewe pair at the Woodbury Mall, (the famed haven for discounted designer shopping addicts, just one quick bus trip away from Manhattan). When I found those, I knew I was into loafers for the long haul. I started to prefer wearing them over my heeled boots, and even cleaned out and consigned a chunk of my closet in an effort to save up for a pricey, lugged sole Gucci version I had my eyes on. You could even say I was “head over heels”.

I won’t admit how many loafers I have collected or how many styles I currently have hearted on my TheRealReal app, but I will happily recommend what’s on my current wishlist and my favorite pairs I’ve had the pleasure of trying. While I will always love wearing a heel, these flat alternatives have found a permanent place in my heart (and my shoe collection). 

Bass Whitney colorblock Weejuns

$110

G.H. BASS

Loewe brown croc slip-on loafers

$690

SSENSE

Hereu Roqueta slingback T-bar loafers

$430

HEREU

Gucci leather lug-sole horsebit loafers

$950

NET-A-PORTER

Roger Vivier Viv Rangers patent leather loafers

$1,545

MYTHERESA

Vagabond Alex penny loafers

$160

NORDSTROM

Gucci Houdan platform loafers

$500

DSW

Tod’s gathered leather loafers

$595

MATCHESFASHION.COM

Prada logo plaque chunky-heel loafers

$950

FARFETCH

Labucq Kitty loafers in cream

$420

LABUCQ

Bass Polly Weejuns

$110

G.H. BASS

Proenza Schouler loafers

$795

SHOPBOP