The wedding invitation arrived in one of those thick, high-quality envelopes that are expensive just to mail. I unfolded the cardstock and everything looked fine until I reached the RSVP information at the bottom. Race Day 2: Del Mar Races.
And suddenly I panicked. Literally stopped folding the invite and had a mini freak-out in my cramped Portland kitchen. Look, I love boozy brunch activities as much as the next girl.
Dressing up and pretending to bet on horses sounds fun to me! But knowing what to wear to the races has always stumped me.
Every Kentucky Derby party photo album on Facebook is full of what basically amounts to costumes.
Gigantic flower/bird/mullet headpieces. Skin-tight dresses that would make it nearly impossible to find a seat on a grassy field. Kill-the-toe painfully high heels.
It’s like being merry exclusively justifies whatever you decide to wear. Plus, I have form when it comes to race-day fashion fails. Three years ago I went to a Derby party here in Portland.
We’re not THE Derby, but this also feels like as big of a tradition in Portland as the real Kentucky Derby is in Louisville. I ordered what I thought was a legit fascinator from some crap website. It was cheap feathers glued to a giant headband with like, a baseball sock poking out of it.
I paired it with some unforgiving bodycon dress from H&M and horrible shoes. One of the photos from that day is still the template for my Instagram “worst pictures of me” collage. I looked like…I was wearing a costume.
Not a “person going to the horse races” outfit, but a “theme costume store sold me this getup and told me it was trendy” outfit. This wedding was going to be different though. Del Mar’s definitely not Kentucky Derby formal, but there are still actual rules and traditions to uphold.
Sarah’s family would also be there. People who would know the difference between stylish and Saturday-night-at-Saturday Night Live themed. Time to do this right.
Fortunately for me, my coworker Janet was originally from San Diego and has spent many a summer at Del Mar. So when I approached her in the break room/area with our single Keurig maker of coffee (this is not an adequate coffee setup but IT’S OKAY CALIFORNIA), she instantly knew what I needed. “Choose one statement piece and keep the rest of your outfit neutral,” she told me while rinsing out a coffee mug. “You don’t want to look like you tried too hard.” She sent me photos from her last trip to Del Mar and I immediately knew she was right. The people that looked best weren’t wearing the most obvious “showstopper” outfits.
They were putting together actual outfits that complimented each other well. They looked put together, but not “costumey.” Structured where they needed to be, flowy where it made sense. Neutral colors with one pop of bold or wild.
The same principles I use when designing graphics for work, basically. This whole epiphany was mildly embarrassing, because DUH KAITLYN but it also made me realize that I didn’t need to dress like Serena Van der Woodsen just showed up. I just needed to dress like a better version of myself.
Then came the budget reality. While Del Mar isn’t Kentucky Royal Ascot horse races money-consuming, “nice” still costs more money than I was hoping to throw at a weekend wedding. So I set a strict budget of $300 TOTAL to get whatever I needed.
Dresses/suits can be expensive as hell though, so when you factor in shoes + hat/fascinator + clutch/purse you really need to stretch that dollar. Dress came first because I felt like everything else would stem from that base. Fortunately for me, the dress code was pretty broad.
Business Casual to Cocktail Attire, so no super short dresses or tube tops, but nothing that OVERLY fancy either. So I started browsing online until I found the perfect dress at & Other Stories (during one of their random sales, of course) – a midi wrap dress in a mustard-y orange color that reminded me of the changing leaves we get in Oregon every fall. It’s quasi-trendy with the three quarter sleeves (helpful for AC and sunburns), has some waist definition that actually works with my desk-job body, and is made of a thicker material that doesn’t cling like an old sweatshirt.
All in all, this dress ended up being $68 on sale (originally $120, obvi) which I felt was perfect. Hats were harder. I knew fascinators were the easiest way to over-do the head portion of this look, but plain hats felt too “plain?” My friend Maya is somehow always effortlessly stylish (she also lives off of Ramen noodles but WHY IS SHE MAGICAL) and advised me to check out vintage shops first. “You’d be surprised how many racing hats you can find at a legit vintage shop,” she said. “Trust me, they’ve been around long enough that there are probably dozens of them at Goodwill, let alone one that specializes in designer clothing.” She was not lying.
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At House of Vintage (AKA Portland’s Church of Secondhand Designer Clothing), I found the most beautiful wide brim hat in camel colored felt. It’s from the 1970’s, has a subtle band detail around the base, and basically made me feel like Greta Garbo in a film about glamorous secrets at the racetrack. $35. And GOOD GOD were hats expensive on Amazon.
I found similar ones for $150+. My last hurdle was shoes. I learned my lesson from my last horse racing outfit that buying painful shoes is a bad idea.
But I had no idea what kind of surface I’d be standing/walking on at the Del Mar racetrack. Grass? Pavement?
Sand? NONE OF THESE ARE FLATTERING TO THIN HEELS. DSW was having a buy one get one half off sale when I stopped in so I kinda felt like I was cheating, but BOY did I stock up.
I found a pair of tan leather block heels with ankle straps that were surprisingly comfortable. I tested them out by walking around Powell’s Books for a few hours and was definitely still able to go home and walk normally after. Pair that with these easy black flats I was also able to justify since I needed them for work anyway and my shoe game was set.
Bags were last on my list, and also something I almost forgot about until I was packing Sunday morning. I didn’t want to carry around my typical canvas tote backpack but didn’t want to drop $200 on a designer clutch. Target saved me again with this cute structured satchel style bag in “cognac leather” (okay it’s leather-like material but IT LOOKS LIKE LEATHER GURL) that was big enough to hold my phone, wallet, andkeys but not distract from my outfit.
Sunday morning came and by the time I had everything laid out in my room I actually felt kind of good about how I looked. Everything complimented each other without fighting for attention. The colors worked together well and I knew I could move comfortably in everything.
Saturday: Driving down to San Diego was stressful though. Self doubting every outfit decision I made. Did I spend too much money?
Did I spend too little? Is my top too plain? Are my shoes too fancy?
WILL I STAND OUT FOR ALL THE WRONG REASONS?? ? Parking at Del Mar and finally getting my greetings kisses from Sarah and her mom, I knew I’d made the right choices. The people who looked best dressed weren’t wearing the most outlandish outfits.
They weren’t competing with each other to see who wore the most expensive-feeling clothes. They had good fabrics, flattering cuts, and accessories that complimented the whole ensemble. I felt appropriately dressed and not sticky-hot from hiding in the shade because my sandals had no soles.
Sure, there were people rocking it fully “costume” but in the best way. Wide brim hats that towered over their heads, form fitting dresses that made me worry about how these women were going to find seats on the grass, ridiculous shoes that were already causing problems by race two. When Sarah’s mom complimented my outfit (including my hat – WHERE DO YOU FIND THESE AMAZING THINGS GOSSIP GIRL) I felt proud of myself.
Actual accomplishment proud, not like I fooled YOU INTO THINKING I SPENT MONEY proud. It took me way too long to realize that what I learned from shopping for this wedding isn’t restricted to “what to wear to the horse races” type Instagram posts.
Anytime you’re given a dress code that feels intimidating or you don’t understand, take a step back and look at the spirit of the invitation.
Racing attire doesn’t mean over-the-top crazy clothes. It means dressing classy and celebrating the occasion by making an effort. Also learn from my mistakes and invest in some good staples that you KNOW you will wear again.
That dress is now my go-to for any fancy daytime occasions. That hat makes me feel fancy no matter what I wear it with. Invest in good shoes people, because there is nothing worse than a cute outfit ruined by blisters.
Most of all I learned that no matter what the dress code is, the most stylish people at any event will always be the ones who feel like elevated versions of themselves, not like they’re wearing a costume. They respect the dress code, sure. But they don’t let it limit their choices.
They invest in nice pieces instead of flashy ones. And they know that dressing appropriately is ALWAYS more important than dressing to be noticed.<
