Derby Fashion Gone Wrong

Vicki Gunvalson
WTH happened here?  I usually don’t share bad fashion, but the celebrity looks at this year’s Kentucky Derby were so awful, I couldn’t help it.  What a train wreck.  Why does everyone look tired, tacky, or just plain sloppy?  Yikes.  I really couldn’t find one look I loved.  So I ask you, who looks the worst?
Debra Messing (so unflattering and makes her look way larger than she is..hate the color too)

Travis Tritt and his wife 

Mary J. Blige

Kellan Lutz (only look that was descent)

Ginnifer Goodwin and boyfriend Josh Dallas

Cyndi Lauper

Steffi Graff and Andre Agassi

Lindsey Vonn

Gail Simmons (notice the Kate Spade bag–at least that’s cute)
All photos courtesy of Yahoo OMG
174103_$19.99 Totes & Reversible Hobos
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  1. I can’t even include Cyndi Lauper into any kind of worst dressed list- she just does her own thing (much like Bjork). I do agree that Kellan looks the most dapper, but I think Ginnifer Goodwin and her dude (he’s totally channeling the It’s A Brad, Brad World look and I’m SUPER into it) come in a close second- although the hat seems a little more like an afterthought. The crazy hats at Ascot totally win over this year’s Kentucky Derbsters.

    Primpin’ Ain’t Easy

  2. It’s funny but I saw a different picture of Debra Messing and thought she looked great! It just shows how difficult it is to be photographed all the time and in so many different angles. ;)

  3. I imagine it’s difficult to find a big colorful hat that looks good on you … I ALWAYS have a hard time finding a hat even as simple as a fedora that I think looks good on me, so I can imagine what I’d look like on Derby Day! ;) Happy new week, sweets!

    Sandy M ~ Ooh La Frou Frou

  4. Oh my. Hats are more difficult to pull off than people think. These are all pretty bad. I like Lindsey Vonn’s look minus the hat, it just doesn’t work with the dress.

  5. Vicki, Cyndi, and Gail all look AWFUL! (And what is wrong with Vicki’s face? She must have had work gone wrong, but it’s all bubbly and strange… Normally I’m not one to notice things like that, but it’s really starting to look scary… You think?)


  6. …actually, I’m no ‘hat expert’ by AAAANY stretch, but… the Derby obviously has the ‘tradition’ of ladies (and some dudes as well) wearing hats… and it seems like the philosophy (to me, anyway) is to go ‘over the top’ as to their gawdiness – i.e., something you normally would NEVAH wear in public… so, from that context, looks like most of these ladies are ‘in the spirit of things’, anyway! Now, as for the rest of their wardrobe…they’re on their own there… :-]

    hope ya had a Gingery weekend, Kori!!!


  7. I am so glad I’m not the only person that noticed how horrific the fashions were! Seriously, where were the stylists?!

    Chelsea (

  8. You’re right, nothing to get blown away by. The men dressed the best, in my opinion. I don’t know, but I like looking at worst dressed as well as best dressed posts. It lets me know they’re just as human as we are, and that calebs don’t look perfect all the time either. Thanks for the post!


  9. Hey Valene,
    I don’t usually comment back here, but couldn’t reply to you because you’re private…although I agree the awards shows often show less than stellar fashion, I have to disagree with you here. The colors combos are horrible (Mary J in bright red, and Travis Tritt’s wife’s pink accents?), the hats are boring, and the celebs look washed up…I’d love to go in and give them a derby makeover! :-) Kori xoxo

  10. I don’t see these as being bad fashion for the wonderful Derby! (Okay, maybe that hat on Lauper is way too large). But, seriously we can find far worse fashion at any given awards show. The Kentucky Derby looks are pretty good in my book!

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