Under $100: 10 Pairs of the Best Black Leather Chelsea Boots for Winter


Under $100: The Best 10 Pairs of Black Leather Chelsea Boots for Winter

I truly think it's safe to say: I have a 'thing' for Chelsea Boots. If I had to pick one flat boot to wear everyday for the rest of my life it would definitely be a black Chelsea boot. Why? Because they go with everything, they’re comfortable, chic, and sleek. The slight point at the toe of a Chelsea boot (all good and true Chelsea boots should have one!) is insanely flattering for your foot and leg line.

Do you have a certain part of your body that you’re not the biggest fan of? For me it’s my legs, so whenever I go shoe shopping I always look at how the shoe looks on my foot AND how it tapers my legs. Shoes are not about just flattering your foot, they are an extension of your entire leg, so you need to take care when choosing a  boot. I never realized the importance of how a shoe shaped my foot until I really started getting more into style and documenting my personal style for Navigating This. Worrying about shoe shape wasn’t something that I thought about, or maybe I did, but I just didn’t realize it. For example, I’ve never worn (and still don’t) shoes or flats that have a very round toe and short toe base. You know, the ballet flats or round toed heels that show your toes a little? Yeah, I don’t like that at all because it makes my toes look squished and cuts off my foot line. It also makes my toes look shorter and throws off the entire proportion of my foot. I only show parts of my toes in strappy shoes / sandals. Again this has nothing to do with how big my feet actually are, it’s how the shoe makes them look.

Find a Flattering Chelsea Boot

So this brings us to the question, what’s a flattering shoe? What will look on everybody. The Answer: A flat black Chelsea boot. The proportion of the shoe is flattering for ALL body types. It doesn’t matter if you have long legs, short legs, big feet, small feet, are tall or short, are thick or thin. Chelsea boots look good on EVERYONE. They are the Kelly Bag of the boot world. They never go out of style, and they ALWAYS look good with jeans, slacks, and dress (see here). I also wear mine with dresses and skirts and think they look great! Read more about what I look for in this pair of shoes here.


It’s Fall and the weather is changing, you probably need some new boots to carry you through the season. I suggest a Chelsea Boot, especially if you’re looking for something you can wear everyday. Do you already have a great black handbag? Awesome, grab some chic Chelsea boots and you’re set until spring. I don’t think women need to own tons of different shoes or bags to be chic or in style. It’s about having a handful of really amazing pieces and working with those pieces to create new looks. Below are some really amazing Chelsea boots all under $100!! I’ve been extremely particular about the ones I’ve picked and I wish I could own all of them. I can’t wait to see which ones are your favorites!


Thank you so much for reading. Enjoy the rest of your day!