So there I was, staring at this wedding invitation from my college friend Sarah – you know, the thick fancy paper that probably cost more than my monthly coffee budget. Everything looked normal until I got to the bottom: “Day 2: Del Mar Races.” And I just… froze. Like, full-on panic mode in my tiny Portland kitchen.
Don’t get me wrong, I love the idea of fancy day drinking while pretending to understand horse betting. But race fashion? That’s where things get terrifying. I’ve seen those photos from Kentucky Derby parties and honestly, most people look like they’re heading to a themed costume party rather than an actual sporting event. You know what I mean – those hats that could double as satellite dishes, dresses so tight you can’t sit down, and shoes that guarantee you’ll be limping barefoot by noon.
I had firsthand experience with this disaster. Three years ago, I went to a Derby party here in Portland (because apparently every city needs to pretend it’s Louisville for one day in May). I bought what I thought was a “fascinator” from some random online store – basically a bunch of feathers and netting that looked like a bird had an unfortunate encounter with a craft store. Paired it with this bodycon dress from H&M that was so restricting I couldn’t even bend over to pick up my dropped betting slip without risking a wardrobe malfunction.
The photos from that day still haunt my Instagram. I looked like I was wearing a costume labeled “Generic Rich Lady at Races” rather than, you know, actual clothes that a real person would wear. The whole outfit was just… trying too hard? Like I’d googled “horse race outfit” and bought the first three things that came up.
But Sarah’s wedding was different. This was Del Mar, which isn’t Kentucky Derby level formal but still has actual dress codes and traditions. Plus, I’d be around her family, who definitely know the difference between stylish and costume-y. I needed to figure this out properly.
Lucky for me, my coworker Janet used to live in San Diego and has been to Del Mar multiple times. When I cornered her by the coffee machine (okay, our single-serve Keurig machine that barely counts as a coffee situation), she gave me the best advice: “Pick one statement piece and make everything else simple. You’re not trying to win a costume contest.”
She showed me photos from her last Del Mar trip, and I immediately saw what she meant. The women who looked amazing weren’t wearing the most eye-catching outfits – they were wearing well-designed pieces that worked together. Clean lines, good proportions, quality fabrics. Basically the same principles I use for graphic design, but applied to getting dressed.
This revelation was kind of embarrassing because it’s so obvious, but also liberating. I didn’t need to transform into some character from a period drama. I just needed to dress like a more elevated version of myself.
The budget reality check hit pretty quickly though. Del Mar might not require Royal Ascot level formality, but “elevated” still meant spending money I didn’t really have. I gave myself a $300 limit total – which sounds like a lot until you realize you need a dress, shoes, hat or fascinator, and a bag that doesn’t scream “I usually carry my life in a canvas tote from Powell’s Books.”
I started with the dress because that felt like the foundation everything else would build on. The dress code said “business casual to cocktail attire” which is frustratingly vague but basically meant no mini skirts, no strapless anything, and definitely no showing up in my usual uniform of vintage jeans and band tees.
After scrolling through approximately every website that exists, I found it at & Other Stories during one of their random sales – a midi-length wrap dress in this gorgeous rust color that reminded me of fall in Oregon. It had three-quarter sleeves (practical for air conditioning and potential sunburn), a waist that actually flattered my graphic-designer-who-sits-all-day body, and fabric that didn’t look cheap. Sixty-eight dollars on sale, down from $120, which felt like a victory.
The hat situation was trickier. I knew fascinators could go wrong fast, but actual hats felt intimidating. My friend Maya, who somehow always looks effortlessly chic despite also being broke, suggested I try vintage stores first. “Racing hats are classic,” she said. “There’s probably dozens of them at any decent vintage place.”
She was right. At House of Vintage (which is basically Portland’s holy grail of secondhand designer stuff), I found this incredible wide-brimmed hat in camel-colored felt. It was from the ’70s, had this simple band detail, and made me feel like I could star in my own film about a mysterious woman at the racetrack. Thirty-five dollars, which was a steal considering similar new hats were easily $150 plus.
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Shoes were my biggest concern because I’d learned the hard way that uncomfortable shoes can ruin any outfit. Plus, I’d never been to an actual racetrack and had no idea if I’d be walking on grass, pavement, or some combination that would destroy anything with a thin heel.
I ended up at DSW during their buy-one-get-one sale, which felt like cheating but also like smart budget management. Found these tan leather block heels with ankle straps – comfortable enough that I could walk around Powell’s in them for hours, but still fancy enough for the races. The second pair was these black flats that I actually needed for work, so the whole thing felt financially responsible.
The bag was last, and honestly, I almost forgot about it until I was packing the night before. My usual canvas tote wasn’t going to work, but I also couldn’t afford some designer clutch situation. Target came through with this structured satchel in cognac leather (okay, “leather-like material” but it looked convincing) that was big enough for my essentials but small enough to not overwhelm the outfit.
Standing in my bedroom the morning of the races, looking at everything laid out together, I felt… good? Not like I was about to perform in a play, but like I’d put together an outfit that made sense. The colors all worked together, nothing was competing for attention, and I could actually move in everything.
The drive down to San Diego was nerve-wracking though. I kept second-guessing myself – was the dress too simple? Was the hat too much? Would I stick out for all the wrong reasons? But when we got to Del Mar and I saw the other guests, I realized I’d gotten it right.
The women who looked most stylish weren’t wearing the most elaborate outfits. They were wearing thoughtful combinations of pieces that clearly worked together. Good fabrics, flattering cuts, accessories that enhanced rather than overwhelmed. They looked comfortable and confident, like they belonged there.
Meanwhile, there were definitely people who’d gone full costume route. Enormous hats that required special maneuvering through doorways, dresses so form-fitting that sitting looked uncomfortable, shoes that were clearly already causing problems by race two. They weren’t badly dressed exactly, but they looked like they were playing characters rather than being themselves.
I spent the day feeling appropriately dressed without feeling restricted. Could sit comfortably during lunch, walk around the grounds without my feet killing me, dance a little during the post-race party without worrying about anything ripping or falling off. When Sarah’s mom complimented my outfit and asked where I got my hat, I felt genuinely proud instead of like I’d gotten away with something.
Looking at the photos later (and actually liking them for once), I realized what I’d learned applies to way more than just race fashion. Any time there’s a dress code that feels intimidating or unfamiliar, the key is understanding the spirit of it rather than just checking boxes. Racing fashion is about elegance and celebration and making an effort – not about looking like a cartoon version of what you think rich people wear to sporting events.
The other thing I learned is that investing in a few quality pieces, even if it means spending more upfront, makes everything else easier. That dress has become my go-to for any fancy daytime event. The hat makes me feel instantly more sophisticated whenever I wear it. Good shoes are always worth the money because uncomfortable feet make everything else irrelevant.
But mostly I learned that the most stylish people at any event are the ones who look like elevated versions of themselves, not like they’re in costume. They’ve respected the dress code without being trapped by it, chosen quality over flash, and prioritized looking appropriate over looking noticed.
Now when I see those Derby party photos on social media – you know the ones, where everyone’s wearing increasingly elaborate hats and poses like they’re in a historical drama – I don’t feel intimidated anymore. I just think about how much more fun everyone would probably have if they focused less on looking the part and more on actually enjoying the event.
That Del Mar day turned out to be one of those perfect experiences where everything just worked. Good weather, decent luck with my very small bets, excellent champagne, and an outfit that let me focus on celebrating Sarah instead of constantly adjusting uncomfortable clothes. Which is really what getting dressed should be about – enhancing the experience, not becoming the main event.
