Derby Fashion: or how not to look like the Queen Mum

Myself, left, posing with my choice for the "Most Stylish" attendee at last year's Boulder Derby Party.

by Anna Jensen

Derby dressing is really not that difficult, but take one look around at any stylish Derby party in any town and it's easy to see that when hats come into focus, a lot of women's style savvy appears to go out the door.  
Although I have yet to attend the event at Churchill Downs, I have attended and been a guest in the Queens Enclosure at Royal Ascot WHILE attending Fashion School in London so that makes me doubly qualified to pass judgement on horse racing attire.  Kidding, only kidding.  Honestly, it is a very different and therefore difficult occasion, sartorially speaking, for ladies and gents alike.  Hats are undoubtedly the centerpiece of most women's outfits today, ranging from exquisite to ridiculous, but why has having an ostentatious or eye-catching one become the thing to strive for?  First, let me backtrack to how The Kentucky Derby became such a fashion and celebrity event in the first place: marketing.  That's right.  Back in the early days of the race, the "Sport Of Kings" had a pretty sleazy reputation here in the U.S.  Racetracks were not a place for women of any standing and races were not at all the kind of social event they were in Europe.   Events like The Epsom Derby and  Royal Ascot required full morning dress, much like what we consider "formal attire" for men, but with a daycoat, and an appropriately fancy dress and accoutrements  for women.  These continental fixtures drew the upper class and were as important as anything else on the social circuit. Derby founder Col. Meriwether Lewis Clark Jr.' s idea was to send a carriage-full of high society ladies around to talk about how they were going to _be picnicking at the horse race and what lovely clothes they'd be wearing to create an aura of chic around the race.  Hats at horseraces have always been a "thing" mostly because they are a stylish way to keep the sun off.  Hats at the Derby and elsewhere didn't become SO outlandish until around the 1960's due to ladies competing to stand out now that the races were televised.  So, whether you are headed for Kentucky, or any one of the wonderful parties going on in Denver and beyond, here are my tips for looking like you belong in Millionaire's Row:

 1. Start shopping early.  If you see a good "Derby Hat" any day of the year in any city or country, buy it.  Seriously.  You know how hard it is to find a special occasion dress when you're under the gun?  Same for a great Derby hat, times 20.  If you are under the gun, you're lucky that this year hat's are so "in" you can find adorable ones everywhere from Target to Charlotte Russe to Nordstrom and many boutiques.  For Denver shoppers I'd say Neiman Marcus has a wonderful selection of quality milliners, after that you can head any direction in Cherry Creek to find a dress to work with it! Which brings me to #2

2. When you're planning your Derby outfit, start with your hat or fascinator.  Fascinators only came into the common fashion lexicon on this side of the pond  after the wedding of William and Kate...and essentially a piece of felt covered by fabric, netting, feathers, etc. and attached to the head in a variety of ways.  The bonus with fascinators is they are sometimes more comfortable, definitely less hot, and they don't give you the dreaded hat-head look once it's removed.  If your hat or fascinator is more ornate, go for a more simple sheath or flowy chiffon dress that doesn't take away from or compete with the hat. 

 3.  You don't need to have your hat match your dress which matches your purse which matches your shoes.  That just looks like you're trying too hard or you are indeed the Queen's mother.  Just make sure there is a unifying theme.  In general- a more elaborate hat calls for a more simple dress, a more elaborate dress calls for a more simple hat.    ​

4.  ​Plan for your footing!  If you are going to a party where your on the grass you really don't want to be sinking in and ruining your heels in the grass.  Either pick up some  "Solemates" heel protectors (Bed, Bath and Beyond or Nordstrom) or find a beautiful jeweled sandal or ballerina flats.  I think with most Derby attire being colorful, and wanting to keep the hat as the star of the show, nude tones are a good choice for footwear.  "Statement" footwear is usually just going to be overkill.   

Kevin Marr, Editor of Sir and Sport Magazine and Mike Field attend the 2015 Boulder Derby Party

 5.  For the men out there, have some fun!  This is such a great opportunity to pull out the pastels, the seersucker, the bowties, bowlers and derby hats. Seeing a man get out of his comfort zone and transform into a southern gentleman, a preppy stud or anything out of the ordinary scores definite points with the ladies.  That said, you don't want to totally look like you're part of the cast for "Newsies" so I'd avoid too much of the rolled up sleeves/vest/cap look that was oh-so-popular last year and the "I'm just gonna put on anything colorful that I can look".  Choose a seersucker blazer paired with khakis and a white shirt, or some cheerful spring-hued pants with a white shirt and complementary hat are good ways to ease into it until you're more confident.  Remember to wear a nice belt and good shoes and if you're really wanting to look smart and charming go with the bowtie...it worked for the men's style winner (below) last year!  

Myself, left, with my "Judges Choice" award winner who I just couldn't resist for his dapper attire and charm! Boulder Derby Party 2015