I’ve been on the hunt for the perfect pair of boots for roughly 3 years now. I’m pretty picky with everything I wear, but I reached a whole new level when trying to find something to put on my feet. I have scoliosis which means a bad pair of shoes can wreak havoc for days. I really can’t tolerate a heel of any kind, and it’s surprisingly hard to find a flat pair of boots!
I was all about the riding boot trend back in the day, but I’ve gravitated towards the bootie style in recent years. (Fun fact: I almost titled this post “The Best Brown Booties.” I would have had a lot of confused people stumbling on this page.) I scoured the Nordstrom Anniversary Sale every year hoping I’d find a good (affordable) pair but wasn’t having much luck. I really wanted something brown, simple, and comfortable enough to handle lots of city walking.
Enter: The Madewell Ainsley Chelsea boot. Guys, I’m obsessed. I had never bought a pair of Madewell shoes before, but I stumbled upon them and fell in love. Fortunately, it was shortly before my birthday, and my mom is pretty good about checking my Instastories. My husband’s cousin also reached out when I posted them, and she said they’ve been her go-to boot for years. Stylish and well made? (Or, made… well? It’s okay I hate myself, too.) Sold!
My biggest piece of advice is to go one size up if you have wide feet. I’m blessed with Fred Flinstone rock slabs for feet, and my usual size 10 was too narrow. I went up to an 11, and now they’re perfect. I’ve worn them for hours at a time while doing a lot of walking, and they require very little breaking-in time. They also come in black and a gold metallic. If you’re looking for suede, there’s a “Ramsey Chelsea” boot, but the heel was too high for my taste.
What’s your go-to pair of boots? Do you prefer the bootie style, knee high, or over-the-knee?