The internet, quite literally, went wild when Sally Fields, then nominated for her third Academy Award, wore sneakers under her red Valentino gown to a Vanity Fair after party. And for good reason, too. Sometimes you just need to forgo the heels and wear a pair of comfy shoes to an upscale event because why not? There are no rules when it comes to what pair of footwear should be worn to certain outings, so why should we care if we’re wearing sneakers to prom or heels to the grocery store? Check out some of our favorite shoes to dress up and down that can be styled with any outfit.
These seem to be the most obvious choice when it comes to dressing shoes up or down. The trend of wearing sneakers on the red carpet goes as far back as the 2000s, when singers like Rihanna and Kanye West started promoting high-end sneaker brands on the carpet in designer clothing. Ever since, we’ve seen an increase in the amount of sneakers worn by celebrities to fancy events, so there's no reason why we can't too. Trainers are the perfect shoe to transition from casual chic to elegant updo given that they can be styled with nearly everything.
An all white trainer can be designed for casual but is easily upgraded to dressy. You can wear sneakers with any workout fit walking your dog or to your next yoga class, but the monochromatic color can also be paired with a mini dress in any shade for an anniversary dinner or date night.
Casual trainers with neutral color motifs like intertwining black and white stripes or all silver lace ups are great for a bit more pop to your outfit. This color palette looks best paired with a black blazer over a white t-shirt and jeans for an upscale casual fit or with a long beige trench over a black maxi dress for toned down elegance. The silver accentuates any dress for a black tie event but also looks chill with a crop top and skirt combo.
Sneakers with specific detailing or bold patterns can easily be worn with maxi skirts and dresses in the summer for days outside while also styled for business casual for workdays at the office. For a fresh look, try a flatter sneaker that's typically worn with jeans to dress up with trousers and a silk top.
Loafers are the epitome of dark academia. The first thing that probably comes to mind when you think of loafers is private school uniforms complete with a plaid skirt and dark blazer. But lately, they’ve really come into their own, making a seamless transition from corporate to casual during the work week. Loafers have been dressed up and down since the days of Audrey Hepburn and Grace Kelly, falling off for a bit in the ‘70s before rising to popularity once Princess Diana made them her staple shoe in the ‘90s.
Lately, loafers have made an appearance as a work shoe that can be worn out and about for an after work drink or to a fancy work event. While typically styled with long trousers, you can dress loafers up with a black mini skirt, sheer black tights and ruched white socks.
Burgundy loafers add a pop of color no matter how you style them, and they definitely complement the monochromatic prep school style. Try pairing them with cherry red socks, a plaid skirt and a cherry red sweatshirt over a white button down for a classy take on the casual school uniform style.
Ifyou prefer a chunkier, more platform option, chunky slip-on loafers work well paired with cropped pants and short skirts. For a more traditional loafer à la Princess Diana style, two tone penny loafers are in for an after-work drink or with a midi dress for a night at the museum.
This one might be surprising, but cowboy boots have made their way to the top of the list of shoes most worn on a night out. Bella Hadid is no stranger to dressing cowboy boots up or down as the model is frequently seen out in her favorite pair of brown M.L. Leddy’s while out with her boyfriend Adan Baneulos.
Most pairs of cowboy boots sold in stores have etched in designs and a stiching pattern typically seen on authentic cowboy boots. They come in various shades of brown, black and red if you want to alternate between colors, taking a page out of Bella Hadid’s book and styling them with mini or maxi denim skirts and a crop top for any occasion.
The shorter version of the cowboy boot are often worn in black, white and silver, each of which can be dressed up or down. If you’re feeling bold, try the silver with a mini dress on your next bar crawl, and if you want a more subdued look, opt for the black under a pair of baggy jeans. If you want an even shorter version, cowboy boots that are just short of an ankle bootie can be styled with bold prints like cheetah for an unexpected outfit. These are fun to play around with, especially if you play around with different colored tights in the winter for a cute concert fit or a day at the outdoor markets.
Longer western cowboy boots may be more of a vibe for a nicer night on the town, with bootcut jeans and a black silk top or a denim mini skirt with pleats. If you’re really into cowboy boots and practically can’t live without them, bright red leather boots are a classic example of a shoes perfect for any occasion. For winter, pair them with longer fur coats for a dressier effect.
