It’s prime boot-buying season. The temperature is chilly, the weather is unpredictable, and your rotation of outfits is heavy on rich textures. Even when perusing affordable shopping destinations like Zara and H&M, boots tend to fall on the more expensive side of the price spectrum, so any pair you bring home will be an investment meant to hold up for more than a single season and work with dressy and casual looks.
To me, the best boots fall into a few key categories, and I always try to make sure I have at least one of each in my rotation any given season. First, there are the practical everyday boots. Think equestrian-inspired or moto styles. These are sturdy, comfortable, and able to handle my daily commute on the subway. Next up, there are party boots. These are styles with a higher heel pitch and may come in unexpected colors or materials, such as horsehair or silver leather. Next, there are the cozies. This category includes Uggs, hiking boots, and rubber rain galoshes. Lastly, there are booties, which I consider the most versatile option of the bunch.
Once I have each of these categories squared away, I’m a little more open to my whims, perhaps picking up a trendy style for the season ahead or opting for a beloved silhouette in a fun new color or material. Ahead, I’ve collected 31 of my current favorites to help you kick-start your lineup of cute boots.