Inspired by Southern Charm: Our Favorite Past Looks from the Kentucky Derby

It’s Kentucky Derby week, and no matter how you may or may not feel about horse racing and its place in the world, it’s not debatable that the Kentucky Derby is one of the most exciting and colorful design inspiration events of the season. After all, how many events truly embrace the majesty of elaborate hats? But it isn’t just the hats that draw us in. It’s also the unique merger of exuberant color and put-together southern refinement that make the styles seen at the Kentucky Derby so alluring. We could go on and on about what inspires us the most about this, but we’re visual people and presumably so are you. So instead we’re putting together a curation of some of our favorite images of past Kentucky Derby styles that make us sit up and take notice.

Fascinators Have Nothing on Kentucky Derby Hats!

Bright and Beautiful Hats: Our Favorite Kentucky Derby Styles

Color, color and so much color. If you’ve even briefly glanced at the Jan Leslie collection, then you’re aware of her obsession with the brightest and the boldest colors. We’re obsessed with this collection of hats we found in an image from the Examiner. The bright oranges and pinks blend together for a color combination we simply like to refer to as chirpy. We truly wish there were an excuse to wear such amazing statement hats on a daily basis. Alas, we’ll celebrate the Kentucky Derby at home with our own chirpy hats!

Bright and Colorful Summer Popsicle CufflinksFor the man accompanying a woman in such a spectacular hat, may we recommend matching her joyful and color-bold choice for the day with our Summer Popsicle Cufflinks in three equally enthusiastic color choices.

A Hockey Great Shows You How to Keep it Classic and Derby-Styled

Sidney Crosby: Our Favorite Kentucky Derby Styles

We admit to being huge hockey fans at Jan Leslie, so we’re always curious what Kentucky Derby aficionado Sidney Crosby of the Pittsburgh Penguins is wearing. He may be sweat and guts on the ice, but we think he’s the perfect picture of how to capture youth and refinement in one look with this Derby look from 2014. It’s a touch of preppy with a touch of celebration.  While he’s sticking with shades of a neutral palette, he’s mixing it up with a loosened tie to let you know that he’s not “too” buttoned up. We love it.

There Are No Words for the Joy of Tara Lapinski and Johnny Weir

Tara Lapinski and Johnny Weir: Our Favorite Kentucky Derby Styles

Of course we were joyful (and admittedly obsessed) when Tara Lapinski and Johnny Weir brought their equally ostentatious love of style to Olympic Ice Skating commentary, so we thought it was pure brilliance when NBC retained them to also commentate on fashion for the Kentucky Derby last year. They did not disappoint. Tara’s goddess hair and Weir’s circle of roses hat? Perfection does not say enough.

We’re In Lust With This 1970’s Throwback

Seventies Style Throwback: Our Kentucky Derby Style Favorites

We’d like to thank Popsugar for digging through photo archives to find some amazing photos of Kentucky Derby styles from decades past. Even though this look is from the seventies, we’re dreaming it will come back! A tailored look for women is hot and on-trend again, and when paired with these unapologetically masculine angled fedora-style hats, it emphasizes sexy femininity more than anything.  Sometimes is not the biggest hat that gets noticed but the most captivating look, and we definitely would argue that this look is fully captivating.

Black and White and Minty

Black and White: Our Favorite Kentucky Derby Styles

What goes better with the vibrant green “accessory” of a Mint Julep better than classic black and white? Nothing! Or, a better way to say this would be to ask what’s the perfect accessory for a feminine printed black and white Kentucky Derby dress with a giant, ladylike matching hat? Obviously it’s the vibrant green of the mint in your Mint Julep!

Of course, we could go on and on, but we’d encourage you to get up this weekend, make your own Mint Julep and watch the Kentucky Derby parade of fashion while relaxing in your home in your own fun fashion choices!

Perfect Dapper Accessories for the Kentucky Derby

Inspired by Southern Charm: Our Favorite Past Looks from the Kentucky Derby
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Inspired by Southern Charm: Our Favorite Past Looks from the Kentucky Derby
We’re taking a look at our favorite styles from past Kentucky Derby events as we get ready for this year’s festivities. And of course we’ve got some style tips.
Jan Leslie