The wrong pair of shoes can derail your entire outfit and your mood. Add to that the fact that “office appropriate” doesn’t always mesh with those strappy Sex and the City Manolos, and that unpredictable autumn weather can be brutal on suede, and you’ve got a recipe for style frustration. The good news? We’ve gathered a lineup of comfortable, wearable footwear to carry you stylishly through the season. Paired with a timeless staple—the classic bootcut jean—these picks are effortless, versatile, and won’t have you limping or regretting your choice five minutes into the day.
Pumps
Sometimes, simple is best, and there’s a reason a heeled pump is a classic. Evolving from the modest heights of the 1950s to the platform heels of the 2010s, within the pump family, there’s something for everyone. The simple bootcut silhouette provides the perfect partner for your pumps, with the slight flare creating an elongating illusion even for those on the shorter side.
Cowboy boots
Cowboy boots have been having a moment this summer, but the original accompaniment for these horse girl faves is the classic bootcut jean – a silhouette that was quite literally designed with them in mind. Whether you lean into full rodeo chic in a breezy shirt or opt for the more boho look, the cowboy boot and bootcut jean combo is a tried and true option, whatever the weather.
Ballet flats
This season, we’ve seen every iteration of ballet-inspired footwear on the streets, but simple flats are the unbeatable option when it comes to a comfy-but-cool shoe. Available in just about any shade and fabric you can imagine, the Noughties classic is perfect for unpredictable days and goes well with everything from a floaty midi-dress to classic bootcut jeans.
Mary Janes
If you’re after a bit of height without sacrificing walkability, Mary Janes are what you want. With their low square heels and secure straps, these are a style that pairs form and function. Just as suited to the office as after-work drinks, paired with bootcut jeans, Mary Janes will see you from AM to PM with ease.
Loafers
Vintage-inspired loafers are huge right now. Thanks to Kendall Jenner, Bella Hadid and Anne Hathaway, these back-to-school shoes are here to stay. Combine them with bootcut jeans, a button-up shirt and a blazer, and you’ve got an easy office outfit that’s simple but still cute.
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