Dylan Dreyer is usually known for polished, classy looks — but her 2019 appearance at the Kentucky Derby didn’t quite hit the mark.
In fact, fans didn’t hold back, calling it one of her most mismatched and confusing fashion moments.
A bold look that didn’t come together
Dreyer stepped out in a light blue dress paired with a bright coral hat — a combo that immediately raised eyebrows.
While each piece might have worked on its own, together they clashed badly, leaving the outfit looking rushed rather than refined.
Even her signature confidence (and killer legs) couldn’t fully save the look.
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Social media reactions were brutal
Fans quickly flooded her Instagram comments with mixed — and sometimes savage — opinions:
- “Hat is bad! But you always look great.”
- “Not my favorite dress.”
- “Nah. Not a fav.”
The criticism wasn’t just about the colors — many felt the entire outfit lacked the elegance typically expected at the Derby.
Even Tom Brady caught strays
In a follow-up post, Dreyer shared photos with Tom Brady and Von Miller — but the internet had jokes for everyone.
One comment hilariously compared Brady’s look to a character from The Mask, proving nobody was safe from Derby fashion critiques.
Derby fashion: hit or miss for Dreyer
To be fair, Dreyer’s Derby style has always been unpredictable.
- 2018: A major win — elegant navy dress, floral details, perfectly matched hat
- 2019: A miss — clashing colors and poor coordination
- 2025: Another debated look — described by some as messy and oversized
Despite the criticism, her willingness to experiment keeps fans watching.
The bigger picture
The Kentucky Derby is as much about fashion as it is about horse racing — bold hats, bright colors, and standout looks are part of the tradition.
And while Dylan Dreyer may not always get it right, her risks are exactly what keep her style interesting.
Sometimes it works beautifully… and sometimes, it becomes a viral fashion fail.
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