When Should You Stop Wearing Sandals and Start Wearing Boots?
When should you stop wearing sandals and start wearing boots for the season? There’s no hard-and-fast date—and these days, the old fashion rules have a lot less to do with the calendar.
Seasonal dressing is increasingly about the weather, the outfit and the occasion. A warm October day may still call for sandals, while a cool September morning might have you reaching for loafers or boots.
Think of your shoes as one of the easiest ways to transition your wardrobe from one season to the next. Adding boots can make a summery dress or skirt feel instantly more fall-ready, while keeping the sandals and layering in denim, knits or other fall pieces can extend your warmer-weather wardrobe without the whole outfit feeling too summery.
So when is it really time to stop wearing sandals—or start wearing boots? Let’s take it month by month.
Sandals or Boots in September?
Sometimes the weather in New England obeys - meaning it gets cool the day after summer turns to fall, which is September 23rd this year. Yet with global warming, there really is not a predetermined day on which all toes must disappear.
We say rock those sandals until the weather turns chilly especially the heartier versions with a lug sole or chunky heel that naturally feel more fall than a strappy version. Warm earth tone colors also transition more easily into your fall wardrobe than sunny brights.
Can You Wear Sandals in October—or Is It Time for Boots?
Did someone say pumpkin spice? Come October it’s officially autumn but there’s no law that we have to pack up all our sandals. Though you can definitely do boots, on those warm sunny days go ahead and mix in sandals to lighten heavier fall pieces like denim or a cardigan.
If you aren’t convinced that it is cold enough yet to unpack your boots, some great alternatives are sneakers, loafers or ballet flats to bridge the transition. Check out our post, How to Style Skirts with Sneakers to explore sneaker looks this fall.
Can You Still Wear Sandals in November—or Is It Time for Boots?
Once the weather is consistently cold, it’s time to cover those toes and give thanks … for great boots! Especially those that are ankle height, whether it be a colorful bootie, a slouchy bootie, or “statement sole” bootie, which we love as our go-to shoe for late fall and early winter.
We love that the knee boot has returned and a classic riding boot always adds style and comfort. On more temperate days, opt for a dress or crop pant with a bare leg to lighten the look. On more brutal days, go ahead and wear heavy tights and warm socks under your stylish boots and achieve both form and function!
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Need help transitioning your style to fall?
No problem! Get one-on-one guidance and advice from our expert Stylists who are on top of the latest trends and style for the coming season! Not only will they help you find fresh new pieces, but they will also help you pair them with existing items in your wardrobe, for endless looks this fall.