The recent overlap between midterm and gnat season has made it… difficult to enjoy the last couple of weeks. The only thing getting me through is the anticipation of the first in-person Dillo Day since 2019.
Given this year’s theme – Return of the Rodeo – the obvious way to start the search for fit inspiration is by scouring Pinterest for cowboy-inspired outfits. From Rango to Brokeback Mountain, Dolly Parton to Orville Peck, there’s plenty of style inspiration to be found in cowboy movies and among country music stars.
That being said, if you want to be more subtle about incorporating the theme – or if you take the route most celebs did at this year’s Met Gala and ignore the theme completely – here are five potential places to start your Dillo style journey.
1. 2000s red carpet fashion
With the exception of kitten heels, which are not ideal music festival attire for obvious reasons, casual red carpet fashion of the 2000s – think Ashley Tisdale – is the perfect source for Dillo fit inspiration. By swapping out heels for cowboy boots like Taylor Swift did in this Academy of Country Music Awards look in 2006, you can easily take a look from the red carpet to the Lakefill. With a new, nostalgia-fueled mindset, outfits like these can be easily assembled by combining items you already own. I suggest starting with this 2005 Rihanna look that is so incredibly important to me:
2. Disney Channel
In a very similar fashion (pun intended), outfits featured in anything that Disney Channel put out before 2015 should absolutely be emulated. Look beyond the excessive Disney layering, which hopefully won’t be needed, to find more summery looks. An obvious choice for Return of the Rodeo is Miley Cyrus’s iconic “Hoedown Throwdown” fit, but you could also begin your search by streaming the second-greatest sequel of all time: High School Musical 2. (Number one is obviously Shrek 2.) Sharpay Evans’ and Gabriella Montez’s summer wardrobes both leave me speechless. Speaking of HSM2, I highly recommend pulling a Ryan-and-Chad-style switcheroo with your friends to create fun outfits without having to buy anything new. Basically, if y’all don’t pull up to Dillo like this, I’m going to be disappointed.
3. Literally just Lenny Kravitz
I tried to avoid naming one person as an inspiration source in this story, but I fell down a Lenny Kravitz rabbit hole while researching and couldn't help it. Can you blame me? If Dillo is as warm as I’m hoping, accessories are going to be very necessary to take people's fits to the next level. From skinny scarves and necklaces to more functional items like sunglasses and belts, Kravitz is the ultimate inspiration. If a button-up top is your go-to concert or festival wear – understandable, it’s a classic – channel Kravitz, specifically his style in the 90s, and build the rest of your outfit around it.
4. Dillo Day’s very own daytime headliner
I didn’t know a ton about Remi Wolf before she was announced as Dillo’s daytime headliner – just a few songs and a vague idea of what she looks like – but she has quickly become one of my biggest style inspirations for the event (and in general). Her Instagram looks like a board I would meticulously curate on Pinterest. Remi’s style has a lot of range but is always (A) colorful and (B) maximalist. While her signature fuzzy hats may not be ideal headwear for a sweaty music festival, some looks, like the one she wears on her debut album cover and this personal favorite, translate a little better. The Remi fit below, for example, has all of the perfect elements of a Dillo fit – comfy sneakers, flowy fabrics, and lightweight accessories that make a statement.
5. Total Drama Island (hear me out…)
Just like that, we’re back to childhood media. Let me clarify – I’m not encouraging that we turn Dillo into a theme party where everyone dresses like a character from the Canadian animated series. Rather, I am arguing that everyone at this school can find some sort of style inspiration in the wide range of aesthetics represented by the show’s contestants. Izzy, Gwen, Lindsay, Leshawna, Heather … all of these characters and more provide easy-to-follow blueprints for unique Dillo fits. And If they can look good in these outfits while running from serial killers and bears, you’ll look good in them dancing to “Photo ID” while day-drunk. And if you are trying to dress on theme, Geoff’s open button-up/cowboy hat combo might just be the perfect look.
Though I hope the end of the two-year-long IRL Dillo drought will motivate people to go harder with their festival fits, I am already mentally preparing myself for an absolutely absurd amount of basketball jerseys – new Dillo drinking game idea anyone? All jokes aside, wear whatever the hell you want and I hope you all have a sexy, safe, gnat-free Dillo.
Thumbnail graphic by Bailey Richards.