I feel like most of us—or at least lots of us—have had one pair or another of these in our closets for decades. My first ones, from the late 80s, were from an Upper West Side store whose name escapes me (anyone remember? It was on Amsterdam, I’m pretty sure, and they sold Doc Martens and other clunky late 80s footwear, and the staff was appallingly rude). Then my next pair was from Freelance, and were purchased from the legendary Otto Tootsi Plohound on lower Fifth Avenue in the 90s. Since those days, I’ve preferred a Chelsea that’s on the clunkier side and I still do, but I like this pair because it manages to look clunky and polished at the same time.
The Chelsea boots I actually pull out of the closet most are, unshockingly, my Blundstones. I quite literally wore mine into the ground and ended up resoling them with Vibram soles and now they’re unstoppable. I also like this insulated pair for the chillier months.
This suede pair is in my shopping cart even as I type. Common sense almost always prevents me from buying suede, but suede doesn’t help matters by being so cool-looking.
Hey, if neuromas, bunions, or some other middle-aged foot maladies don’t prevent you from wearing pointy-toe boots, you could do worse than these; also, this pair from Madewell mines a similar vein for cheaper.
These are a bit more fashiony that I usually show, and I couldn’t wear them for more than an hour (that I spent mostly sitting), but I do think they’re cool.
From Vince, the ideal streamlined tomboy shape, with a bit of a platform sole.
I like the longer shaft and cap toe on this snappy pair.
And finally, a nicely streamlined pair that’s maybe worth the investment.
They NEVER go out of style! I've had the same ones for more years than I care to cop to. 😁 Love these posts because no matter what "hard stuff" I'm doing in a day, they represent a very welcome relief...nothing like a bit of "pretty" to lift a "Girl of a Certain Age's" spirits. 💜
Could we possibly get the fashion tips and rules around how to style Chelsea boots? What kind of pants look best/worst? Are we doing these with cropped pants only? Are leggings acceptable these days? I looove these boots but I'm always worried about which pants I am supposed to wear with them. Thank you!