We already detailed our search for
The Boot: The Dicker by Isabel Marant
Pros: They're a cult classic, beloved by style icon Kate Bosworth, and we've never seen someone not look super chic while wearing them. They're also only 2.5" high, so, comfort.
Cons: They're pretty ubiquitous, a little trendy and there are a ton of knock-offs, some of which are pretty convincing and a whole lot cheaper. Still, none of them quite match up to the original. They just have that je ne sais quoi. Though suede is a little tricky to wear year round if you live somewhere that has seasons and might therefore rain on your expensive shoes.
The Boot: The Pistol by Acne
Material: 100% Calfskin
Pros: With smooth black leather and a clean silhouette, these guys are tough but still sleek and put together. And apparently the ankle hits at the most elongating part of the leg, so that's always good.
Cons: We can't really think of any, other than the fact that they're a bit pricy--it's mostly about personal preference.
The Boot: The Rover Bootie by Marais USA
Material: Nubuck leather upper, leather heel
Pros: Not suede, clean silhouette, pretty affordable and a pretty short 2" for those afraid of heights.
Cons: They're on the pointy side, so you'd have to be into that. Marais shoes are also tricky to find in stores, so you may have to buy them online without trying them on. Though, we've never been unhappy with a purchase from them.
The Boot: The Newbury by Rag & Bone
Material: Lambskin leather
Pros: Very cool, universally flattering, and a little more affordable than the Dicker and the Pistol. Plus, everyone says they're incredibly comfortable and we love the worn-in look.
Cons: They're pretty ubiquitous and a little slouchy.
The Boot: The Mars by Rachel Comey
Material: These are calfskin leather, but they come in a variety of fabrics.
Pros: They're low and comfy, the cheapest of the "designer" booties and have a hidden elastic on the inside for extra comfort, making them easy to put on without a zipper. And they're a little less ubiquitous than some others. Also, I'm wearing them right now and you definitely want to dress like me.
Cons: They're a pretty specific look and may not look good on everyone. To me, they're very Brooklyn.
The Boot: The Zip Code Boot by Madewell
Pros: They're pretty affordable and kind of the perfect marriage of the Mars and the Dicker--a leather upper with a stacked wood heel.
Cons: It's honestly tough to think of any. They may not be as elongating as some others.
The Boot: The Bright Fire High Heel by Joie
Material: Suede/leather upper, leather lining, leather sole
Pros: 4" if you need some height, cool two-tone effect, chic, pointy silhouette.
Cons: Maybe a little tall/dressy for everyday, depending on what kind of person you are. Also suede = bad for rainy situations.
The Boot: The Jodhpur by Swedish Hasbeens
Material: Leather upper, leather lining, rubber sole
Pros: Super practical, comfortable and they say to the world, "I'm a person who's cool and hip but also cares about comfort."
Cons: They're kinda weird-looking.
The Boot: The Eliana Double Zip Ankle Boot by Ecote
Material: Faux leather
Pros: Looking for a cheaper version of the Pistol? Here it is. This is probably the best looking under-$100 bootie you'll find.
Cons: It's faux leather; the graininess looks a little cheap and these probably aren't going to last you that long.
None of our picks strike your fancy? Here are some others that may appeal to your tastes. Clockwise from left: