With another Kentucky Derby in the books, it’s time to get down to the most entertaining portion of the Derby and that’s the people-watching. Only at the Derby can tell the personality of someone before you approach them based off how obnoxious/classy their hat is.

From celebs to casual fans, this year was no different. Some are beautiful and others are tragic, but they are all entertaining.

Nick Lachey & Vanessa Minnillo

Both huge sports fans and Vanessa always looks great. I think I’m partial to the smaller hats rather than a huge hat.

Aubrey O’Day

The former Danity Kane member on P Diddy’s Making the Band is doing porn by now right? If she’s not, its only a matter of time.

Maria Menounos

I’m a big fan of Maria and when I first saw the hat, it looks cute but paired with her dress, I wasn’t a fan. Its a little much. Though from the neck up, she looks fabulous.

Erin Andrews

Speaking of how important the “whole Derby Package” should look, Erin Andrews pulls this off fantastically. The picture of her neck up is cute, but seeing her in the whole outfit, the only words that come to mind is just “Wow”.

Lindsey Vonn

Its hard for the Olympic skier for the US team to NOT look good.

Betsey Johnson

Even fashion designer Betsey got behind a program for Breast Cancer raising money for every one of her hats sold. Her style is usually very flirty and eccentric, which means a perfect combination for a Derby Hat.

Marissa Miller

I really doubt if I typed anything here, anyone would read it after the words “Marissa Mill…” are read.

Tom Brady

I want to try and not make fun of the NE Quarterback as I think this outfit is actually pretty damn cool, but the fact that it is Tom Brady wearing it, just makes the outfit lose a touch of cool factor. I’m not sure why and it doesn’t make sense, it just is.

Classy Hats

Your hat shows your personality, so should you wear a classy or goofy hat, chances are your personality will shine brightly through it. Another Derby, another chance for a great people and hat watching. Here are some of the best we found…


Crazy Hats

Photos courtesy of E Online, Sports Grid, Styleite, and Terez Owens