We follow trends, we buy into them, let them vanish and then wait until they find their way into the scene again. That’s just how it is, and it applies even to other parts of our outfits, including footwear. But we find that sometimes, it’s worth a lot more to invest in pieces that have more than just long shelf lives—they’re also versatile enough that even when they’re picked up every time, no one would dare question the choice. The reliable Chelsea boot fits the bill, and is a great addition should you want to spend on booties that you can maximize. Although they now come with more unconventional elements, the classic appeal is still there, guaranteed to put your shoe rack into a better state.
This fall, add more to your collection by shopping for the season-appropriate shoes, some of the kickiest pairs already rounded out below:
1. Trademark Delphine croc-effect leather ankle boots
Made in Italy, the Delphine Chelsea boots, courtesy of Trademark, is an utter delight to the eyes. The croc effect in the chocolate-colored leather is lovely, and it is flexible enough to look stately with bottoms of your choice. They are made more desirable with the ease one can pull on and off the shoes.
2. Tod’s low heel ankle boots
You can trust Tod’s to deliver in producing a sturdy pair of boots, but these shoes also help show the chic in you with its slanted heels that look amazing with denim. Italian-made, these Chelsea boots also feel luxurious with its soft suede.
3. Alexander Wang Spencer Boot
When done right, animal prints can be worn throughout the year. Just take a look at these Spencer boots from Alexander Wang—the leopard print is exquisite on the military-inspired silhouette. It can be worn regardless if you’re shooting for a feminine or rock and roll look. What’s more, the Spencer can easily be the highlight of your getup.
4. Saint Laurent Loulou 50 suede Chelsea boots
We can’t get enough of Saint Laurent’s Loulou Chelsea boots. Even though it relies on a classic silhouette, the shoes are made more covetable by their ease of wear and the top quality construction. The black suede is complemented by the block heel bearing a logo of the label.
5. Rag & Bone Alsen patent-leather Chelsea boots
The Rag & Bone Alsen has just the right amount of edge we need from our good ol’ Chelsea boots, making them the perfect pair for denim and leather. The heels, measured at around 3 inches, help elevate the look, but so does the black patent leather, constructed expertly in Italy.
6. Common Projects Suede Chelsea boots
Common Projects’ boots are made for season-to-season wear, and that’s not just because it takes on a classic construction. The color, besides being in lovely pastel, is a chic match for many dresses, skirts and pants, regardless of the temperature. The plush boots are made in Italy with velvety suede, and are equipped with comfortable rubber soles that treat the feet with each step.
7. Ludwig Reiter Suede Chelsea boots
Ludwig Reiter has a long history of creating impeccable and durable booties, and these shoes only add to the already expansive list. They have a modern edge despite being Chelsea boots, and with time, they’re promised to look even better. Pair these with cropped jeans for the shoes to have more impact.