This article was written by The Zillennial Zine’s spring editorial intern Erin Galioto. Find her on Instagram at @eringalioto. If you would like to share an article with The Zillennial, send us an email at thezillennialzine@gmail.com.
All the shoes in my closet mostly fall into one of two categories: medieval torture or exercise equipment. My little kitten heels and leather stiletto boots hold a special place in my heart and are worth every blister and foot cramp they give me. You couldn’t pry them from my cold, dead hands. Despite their impracticality, I would go as far as to wrap my foot in gauze just to sustain wearing these shoes to work. However, since my move to a walkable neighborhood, I feel increasing pressure to move towards footwear with less height and more cushion. Flip-flops sustained me through summer, but fall is creeping in and toes in the wild are no longer acceptable. I’m not willing to sacrifice style for the sake of comfort, so I have composed a list of fashion-friendly shoe options that achieve both.
Clog
The clog is the baggy pant’s best friend for an effortlessly chic look. Birkenstock of course has the iconic Boston slip-on clog and even has fur-lined options for colder months. Other clogs, like this pair from Zara, play with print to add interest to a neutral fit. While we still have some warmer weather, peep a little leg and wear your clogs with jorts and slouchy socks styled with a wife-respecter and crewneck sweatshirt or sweater that can be taken off and tied around your shoulders for a cool-girl casual-vibe Emma Chamberlain would approve.
Boot
The Frye Campus boot took off majorly as a trend for Fall 2023. While they may have been trending, these boots are more classic than trendy and have a reputation for quality and durability. Insider secret: The RealReal has a great selection of Frye for very reasonable prices. Personally, I have found several Frye-esque leather riding boots at every thrift for a bit cheaper as well. The horse-girl approved footwear will keep you comfortable all day and they are the only shoes I wear to music festivals and flea markets.
The rainboot, or wellies as the Brits call them, are another boot resurgence I love for fall. This glossy red pair from Hunter will look great with ivory lace and a tan trench coat. Fashion influencer Hayley Knowles opts for a classic Burberry printed pair to style her fall looks. NY Fashion Week saw several other styles of flat boots including mid-calf boots and slouchy knee high boots that both look adorable paired with a mini dress. I’m really loving this grey pair from Yume Yume. To add a playful 60s‑inspired twist to the same look, try Gogo boots by Melissa a glossy go‑go silhouette that really pops with mini dresses.
Ballet Flat
Ballet flats exploded back on the scene last season and brands have been designing every iteration under the sun. The ballerina staple has several great neutral options that can read very “office siren” if done right. Pair these black flats with a neutral capri pant, a tight, long-sleeve top or cardigan, skinny reading glasses, and a messy hair pin updo to get the look. This lace-up version from Etsy can be styled with a black midi skirt, blouse, and pearls for a Simone Rocha x JPG look. Still not satiated? Achieve a Ramona Flowers, “manic pixie dream girl” aesthetic wearing retro-futuristic ballet flats like the ones below with your favorite vintage jacket and patterned tights.
Mule
The mule is the LinkedIn-approved flat for fall. I love a pointed mule under a wide-leg pant because it gives the same silhouette of a stiletto boot or a kitten heel with all the comfort. Style a pair like these from Everlane with wide-legged denim, a loose button-down under an oversized, cable-knit v-neck sweater, and a slouchy suede tote to wear while sipping Pumpkin Spice and looking mysterious at the coffee shop.
Sneaker
When the rest of your outfit leans more polished, adding a sneaker can be the perfect element to play up the cool factor. Try applying Allison Bornstein’s “Wrong Shoe” theory: whatever shoe you would traditionally pair with an outfit, pick the opposite, and the result will be instantly chic. For instance, pieces like blazers, dress pants, and tailored skirts are from a different world than an athletic shoe, and that’s exactly why they look so cool paired together.
Loafer
My style tends to lean feminine and girly, so I initially had an aversion to the loafer. However, the loafers from Sandy Liang’s recent collection have completely won me over. Going back to wrong shoe theory, it would be interesting to pair the heavy, masculine style of the loafer with something feminine, light, and airy. Think a flowy or perhaps ruffled slip dress or even a tutu! Loafers are also great for invoking Rory Gilmore’s bookish fall aesthetic when paired with dark denim, plaid, and earth-toned knits.
Toe Shoes
If you’re looking at that heading with shock and disgust, you are not alone. Just like the Margiela Tabi, toe shoes may not be for everyone. Trend forecaster Anya (@fashunadict) does a great job breaking down why they might sneak their way into the fashion world. Are you brave enough to give it a try before it hits mainstream? Look to influencer Jessi Regina’s styling of her white ballet-adjacent toe-shoes with a sporty top tucked under a black corset and black voluminous skirt. I’d be lying if I said I wasn’t intrigued…
Shoe Inserts
These shoe options may fit the bill for being low to the ground and stylish, but these days comfort isn’t always a given. To give your feet some extra love, try installing some shoe inserts. I love these ankle pads for ballet flats to avoid friction and blisters. Plantar pads like these from Amazon are great for mules and any other shoe that has no strap or backing touching the ankle. Full orthopedic insoles are great for all sneakers and most boots. If you feel your feet are aching more than usual, visit an orthopedic doctor for more insert recommendations.
When you are looking for comfortable flat shoes with support, what’s your go-to pair? Let us know in the comments below!
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