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A guide to dressing for the Derby and other horse racing events!

Posted April 08 2019

Derby Dressing Guide

It's the first Saturday in May, 
Louisville, Kentucky. The sun is shining, the ground is a bit muddy, Spring has finally arrived. The aroma of fresh cut grass mingles with a waft of manure. Mint & bourbon quench your thirst as you toast the day. A horn rings out ceremoniously, signaling the arrival of some very important 4-legged athletes.

You can feel the buzz of excitement in the crowds around you. A stray feather from a bold fascinator blows past in the wind. As the band strikes up 'My Old Kentucky Home', you sing along with friends old and new. The excitement reaches a crescendo, and they're off!

Two minutes later, you celebrate victory or defeat. Roses are strewn upon the victor. More bourbon for the loser. The first leg of the Triple Crown has been settled. Happy Derby Day.

Alternatively, you could be like millions of more Americans, and be viewing this whole scene from the comfort of your couch!

The majority of us will tune in for the biggest horse races of the season from our local bars, or a party hosted by friends. What to wear to this party, you ask? Let's delve in!

Not a horse enthusiast? Not a gambler? Not a problem!

Half the fun of the races is dressing up, the other half is the booze - and we have you covered on the outfit.

Horse Races have always been a place to see and be seen, so your outfit must stand out in the crowd...or your living room. The brighter the better, and if you can throw in a Horse related pattern/embroidery, even better!


Outfits

Pastels are the hue of the Spring season. Wear them as Pants, Shorts, in the patterns of your Shirts and Dresses. A light Blue or Green Pant is just the right amount of color, paired with a bold check Shirt, and topped with a trusty Navy Blazer.

Complete the look with the 1920s inspired classic Boater Hat and a Bow Tie and you are, as they say, off to the races!

If you are not a pastel pant kind of gent, a well-tailored Grey Suit with touches of color in the Tie and Shirt will also feel Spring-y, yet not out of your comfort zone.

For ladies, dressing up for a Derby party is more fun, and certainly takes longer to plan, than the horse race itself. The fabrics of the season are Seersucker and Linen, and we cannot wait to pull them out from the back of the winter closet. Cocktail attire is the dress code for most horse races. A Cocktail Length dress will hit just above the knee and have a flattering fit at the waist. A Tea Length is also a great race day option, hitting at mid to high calf.

Bold colors are a great look, with some interest added from a flouncy sleeve or embellishment.

If you are going a more subdued route with your dress color, spice up your outfit with a colorful accessory, such as a hat or gloves.

A more casual look for an at home race party is a classic Tunic Top paired with tailored white pants and a cute raffia style wedge. As with the Mens style, any Horse related embroidery or patterns, i.e. horses, roses, etc are a great way to play into the day.


Shoes

Now let’s talk footwear. While the jockeys don their knee-high leather boots, you will find a classic Driving Moc more suitable. A loafer or moc with a gold or brass Bridle Bit accent adds in a horse related aspect and is a staple in every man’s closet. Invented and popularized by Gucci in the 1960s, the bridle bit on the top of the shoe is purely for aesthetic purposes.

If you are at home, or in the more casual sections of the infamous Infield at the races, a Boat Shoe is more comfortable and dressed down style to wear. This option is also a wardrobe staple, and good for year-round wear. Both styles are commonly worn sans socks. As the horse races are during the spring and summer, this sockless look works. If we experience a chilly early May, a bright stripe or whimsically patterned sock will add some fun to your look.

As you will be on your feet most of the day cavorting and watching the race, footwear for the ladies has to fit the seemingly impossible combination of comfort and style. A stylish high heel is the automatic go-to paired with a fancy dress, but we suggest looking into a wedge heel as well. If you are in the infield or a party, a more casual sandal such as a classic Jack Rogers is the way to go.

Depending on weather conditions, the infield can become a mud pit, and the stands are out in the rain. Both Men & Women alike may opt for Wellies or other stylish Rain Boots if the day calls for showers. There is a plethora of stylish looking rainwear nowadays from boots to coats, so your well-curated outfit will not be ruined!


Hats

By far the most iconic accessory associated with Horse Races is the Hat.

Both Men & Women will find their outfit incomplete without a chapeau.

The first Kentucky Derby was run in the year 1875, and the crowd was a sea of straw Boater Hats. You know the look: woven straw with a surrounding brim, traditionally adorned with a navy and red ribbon. Broad enough to provide sun protection, woven just loose enough to allow the breeze to flow through. Whether it be a Fedora, Bowler, Boater or Panama style hat, straw fabric reigns supreme.

On the ladies side, southern belle inspired wide-brimmed straw hats are the most popular.

Decorated with flowers, feathers or bows to express the wearer’s individual style. Although it is not required, it is considered good luck to wear a hat to the Derby!

Hats for women can range from chic & simple in the stands, to costume looking in the infield. A rule of thumb for choosing your hat is to make sure it pairs well with your dress. If you chose a more demure dress, you can add your excitement in your hat. If your dress is a bold pattern, we suggest going a more classic & subtle route for the hat.

A newer trend seen at Races around the country has been the Fascinator. Made from a small woven disc, and topped with feathers and netting, the fascinator is attached to the head via a comb or headband. This is a great headwear option, as it will not give you hat hair!

British aristocracy and wedding guests alike have been donning the ladylike fascinator for years. The fashionable new generation of British royalty, Kate Middleton in particular, have re-popularized this look.


Common Themes

When planning your outfits for the Derby, Belmont Stakes, Preakness or any other seasonal race, keep some themes in mind. Horse Racing has some of the most recognizable symbols in sports, which can add some fun flair to your outfit!

Roses, Bridle Bits, Horse Shoes, and Jockey Silks are some of the best themes of the races from which to pull inspiration. Bits and horseshoes on your Tie, Bow Tie or Pocket Square are a great tie into the event. Printed roses are a pretty pattern for a dress, and also make a colorful Tie print.

The racing silks that are worn by the Jockeys are always fun to watch. Each Jockey wears a different colored and patterned silk top, which signifies the horse’s owner. Perusing the archives of racing silks can provide great inspiration for your own outfit, and help with party planning!


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