Truth be told, there are no hard and fast rules in fashion. Style is just too personal a thing to really pin down with strict guidelines on what looks “good” or is being worn “correctly.” However, I do stand by the idea that rules can be incredibly helpful if you’re not sure where to start when building an outfit or in those moments when you just can’t be bothered to put a lot of thought into what you’re going to wear. They are a secret weapon for creating a no-fail wardrobe full of pieces you can feel confident pairing up knowing you’ll always look put together and stylishly chic. To that end, here are four rules I use for deciding what shoes to wear with skirts to ensure your outfits are on point every single time.
I’m a Fashion Editor—Here Are My 4 Rules for What Shoes to Wear with Skirts
mini, midi, maxi
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Updated Oct 17, 2024
Jeremy Moeller/Getty Images
Jeremy Moeller/Getty Images
1. The Shorter the Skirt, the Shorter the Heel
A great rule of thumb for choosing the best shoes to wear with short skirts is to remember that the shorter your hemline gets, the lower your heels should be. A micro mini worn with sky-high heels will really throw off your proportions and make your torso look squashed, but a kitten heel or pair of flats looks much better. (Don’t worry, your legs will still look miles long and fabulous, even in a flat boot.) And while you definitely don’t have to wear your longer skirts with heels, it can help define your figure a bit amidst all that fabric.
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2. Leave at Least One Palm-Length Between Your Hem and Your Shoe
I love to use this rule for both dresses and skirts, specifically in maxi lengths, to avoid dragging your whole outfit down, making it feel bottom heavy and dowdy. The rule suggests that there should be at least one palm width between the top of your sneaker and the hem of your dress. Or, if you’re opting to show off your socks with a colorful or sporty ankle or calf sock, you should leave one palm width between your sock and the hem of your dress. This helps keep your proportions in check so you won’t be swallowed whole by a full maxi skirt.
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3. Keep Your Vibes in Line…
Sometimes the most obvious shoe is the best shoe. Tennis sneakers with a tennis skirt, loafers with a pleated midi, sandals with a linen wrap skirt—feel free to lean into the idea of “first thought, best thought.” Consider where you are going and the inherent aesthetics of your clothing, be it office-appropriate workwear or sexy date night cocktails, and choose the shoe that best fits the tone.
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4. Or Go Totally Wrong
The Wrong Shoe Theory asserts that your shoes and your clothing don’t need to have the same vibe in order to look great together. For example, you don’t need to wear your workout sneakers only with leggings and sweatshirts—they can look even cooler when paired with jeans and a blazer or a dress and trench coat. In testing this theory myself, however, I did find one asterisk I’d want to stick on the Theory, which is that swapping fashionable for practical works much better than the opposite. Replacing simple Keds with a sky-high stiletto heel felt far too mismatched for loose denim. So if you’re going to go for an “opposites attract” moment, try replace your go-to shoe with something that feels much more practical, like swapping flats for sneakers or heels for loafers.
