Tara Lipinski Tries on Kentucky Derby Hats - Vote for Your Favorite (and See What Johnny Weir Thinks She Should Wear!)

05/02/2014 at 02:11 PM ET

Tara Lipinski Kentucky Derby hatsCourtesy Tara Lipinski

Tara Lipinski and Johnny Weir were the talk of the Sochi Olympics thanks to their spot-on commentating and always on-point fashion choices. And now the dynamic duo is bringing their show on the road — first to the Oscars (see their very memorable try on session here) and now to the Kentucky Derby. Lipinski and Weir debuted their first fabulous hats today, with many more to come over the course of the weekend. And Lipinski was kind enough to take us inside her hat-shopping session before she left town. Check out her options and make sure to watch Johnny’s top topper advice for his pal, all below.

Obviously Lipinski is incredibly excited for the fashion, but second most of all, she says she can’t wait to immerse herself in the Derby experience. “I love the charm and lifestyle of the South so going to the parties and seeing all the amazing outfits and hats will definitely be a highlight,” she tells PEOPLE. “I also can’t wait to attend the parties and maybe try my first mint julep. I might bet on the race so you can be sure I will be screaming along the sidelines for my horse.”

And as it turns out, she has a little horse sense already, from her pre-skating years. “I have never been to a derby before. I owned a horse when I was younger and used to ride but it’s a very expensive sport and I had to choose between that or skating,” she says. “Probably made the right decision! With that being said I have such a passion for the equestrian culture and am beyond excited to attend.”

The former Olympic figure skater’s marathon styling session included tons of dresses (see above), shoes and — of course — hats, but she had a definite plan in mind. “The dress definitely came first,” she said. “My stylist and I were torn because there were so many amazing [hat] options, it was very hard to decide. We needed to see pattern and style to really decide what direction we wanted to go with for the hat.”

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Tara Lipinski Kentucky Derby hatsCourtesy Tara Lipinski

Lipinski kept an open mind when trying on her many options. “I have never worn a hat like this so I didn’t really know what to expect,” she says. “I love fascinators so I was drawn to them immediately but as I started trying on hats I realized I loved the unique shapes and angles. My hats were custom made by Louise Green and she is one talented woman!”

She gave us a preview of her top five picks, above. Clockwise from top left, she says of the ladylike white full-brimmed number, “This one has the big straw hat vibe going on that I usually love to wear — it makes me think of summer. I also found the shape interesting, the bent angle on one side adding some edge and flair.” Of the graphic black headpiece, “This is one of my favorite fascinators I tried on. The design is so fun and interesting, very chic and modern.” And the feathery pink one was a hit: “I loved the feel of a pillbox hat with this fascinator. The soft pink and white colors caught my eye!”

The large pink floral hat gave her ’90s flashbacks in a good way: “I love flowers but usually don’t wear very big ones on my hats. The last time I wore a Blossom hat was a long time ago but the proportions worked on this one. The flowers are so perfect, it looked real!” And finally, the super-girlie crisp white topper was a prime contender. “A white hat always stands out. I loved the softness of this head piece. The veil illusion is fabulous. Definitely a bridal vibe but paired with the right dress it will exude freshness and a crisp look,” she said.

She sent all her options to Weir for the verdict — check out his video, below. Will the two be coordinating at the Kentucky Derby? You bet. “We always find a way to tie something matching in. There will be a pink moment!” Sounds like they’ve already bet on a winner!

Which hat is your favorite? Do you agree with Weir’s assessment? Tell us in the comments!

–Alex Apatoff

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Showing 8 comments

Bob on

I hope Tara chose the light, airy, youthful, white outfit. It suits a spring, outdoors, day event. Large hats overwhelm her doll-like proportions, so no to them. I do like the 40’s acorn cap style on her. (She’s so cute in anything!)

Fran on

I love the white SHERELS HATS fascinator. Just looks so glam and brightens Tara’s beautiful face!

Phil Cheeze on

Are she and Weir a couple ?

Caroline on

Tara Lipinski LOL? How is she even relevant? Is this 1995???!!!!!

ProudAmericanWoman on

Johnny Weir prancing around in ladies hats and basically cross dressing on national TV is just sick- a disgrace. I’m terrified at what is considered normal behavior these days and presented as acceptable to children. Boys and men of tomorrow are so doomed (and therefore the girls and women). God help us.

Karen on

Give these two a show already!

sue on

Are those cheeks real?

Sacrè on

Please stop trying to make these two happen. It’s NOT working.

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