I don’t love the weather in Florida, but one perk is that it rarely gets too cold. That means I can wear peep-toe shoes year-round. I like to dress for the season and layer for fall, but instead of sticking to sandals all year I try to find a middle ground. This year I’m looking for the perfect pair of open-toe booties: a semi-chunky heel at a comfortable height, a side zipper, ankle length, and under $100. My current booties are in good shape but the heel is too high for everyday wear. I want a versatile style I can wear with shorts, skirts, and jeans without looking overly dressy.
Below are the options I’ve narrowed down.
Make It Strappy Bootie — $55
This pair is cute, but the ankle straps might feel bulky and could be unflattering on shorter legs. They have a fun, detailed look, but I’m unsure whether the strapping will work with every outfit.
Night Bootie — $49
I almost love these. The two-tone colorway is interesting, but I prefer booties that pair effortlessly with everything in my wardrobe. These would look great with a midi skirt and a chunky sweater, and I’m tempted to get both colors — but I’m trying to stay practical.
Two-Toned Booties — $55
The two-toned option is stylish and has a slightly edgier vibe. While it’s not a completely neutral option, it could still work well with casual outfits. I’m weighing whether the added detail is worth narrowing the number of outfits I can pair them with.
Overall, I’m leaning toward a bootie with a simple silhouette, a comfortable mid-height heel, and a side zipper for easy on-and-off. Neutral colors will give the most versatility, but a textured or two-tone pair can add personality for specific looks. I’ll keep hunting for something that balances comfort, versatility, and style without breaking the $100 limit—though I’m not ruling out buying two pairs if they complement different parts of my wardrobe.