Tiered mini skirts, Juicy sweatsuits, the rise of Uggs, glitter makeup — I navigated the 2000s testing out each of these trends. But, of all the things to come out of the early aughts, cowboy boots were a personal obsession. Yes, once designated to rodeos and ranches, the distressed, embroidered footwear came unexpectedly — and briefly — to rule the trend cycle nearly 20 years ago, and has seemingly returned to reclaim some fashion territory (along with a number of other trends from that decade). Considering my torch for the style has never truly burned out, I'm incredibly excited to find fresh ways to wear cowboy boots this fall.
I purchased my first pair of Western boots when I was 19. The year was 2004 and Sienna Miller championed the style by wearing many a pair on a number of red carpets. I, of course, promptly scooped up some camel-colored, knee-high leather cowboy boots with an elaborate white butterfly design. After wearing them to the bone for most of that year, by 2005, the trendy shoes slowly made their way to the back of my closet as other shiny new shoe styles came to focus (hello, UGG boots).
Fast-forward some 15 years and, like everything else from the 2000s, cowboy boots are officially back. Thanks to brands like Ganni, Brother Vellies, and Isabel Marant (to name a few), the boot that's often been seen as kitschy or costumey has been transformed via thoughtful detailing, embroidery, and sleek silhouettes. As a strong loyalist to all things early millennium, I'm clearly on board.
That said, with time and age comes wisdom, and the unfortunate style choices I made as a 20-something are definitely behind me. At 34, I've been reacquainted with my beloved cowboy boots (I still have the same butterfly-printed pair!), and this time I'm approaching things a little differently. The frilly micro-mini dresses and frayed denim skirts I emphatically paired with my boots of yore are long gone and, these days, I've found elevated and sophisticated separates make for the best options. Oversized check blazers, chic shirt dresses, and high-waisted leather shorts have all proven to be great matches for footwear with a little western flair.
To prove how far I've come, ahead, the three grown-up ways I'm wearing my cowboy boots in the fall. We're finally reunited, and it feels oh-so good.
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How To Wear Cowboy Boots In The Fall: With Tailored Separates
One of the best ways to lend some sophistication to your cowboy boots is by pairing them with classic, high-quality pieces. Tailored blazers and bootcut denim are a great place to start.
How To Wear Cowboy Boots In The Fall: With A Dress That's Not Of The Prairie Variety
Although voluminous prairie dresses might be the trend du jour right now, when paired with cowboy boots, they can put you in kitschy territory. Instead, opt for a simplistic streamlined style — like a crisp shirtdress — to balance things out a bit.
How To Wear Cowboy Boots In The Fall: Opposite's Attract
Opposites attract in the best unions. And while leather shorts, cozy knit sweaters, and western footwear might seem like they hail from different parts of the fashion universe, when united, they can create perfect harmony.