Kentucky Derby Style: Race Day Ready with Vineyard Vines + 20 Questions with Derby Drew

Alright, we’re really doing it friends. Drew is making his real debut on the blog. I mean, he was in this post but he was an unwilling participant. Today we’re going all in.

A fun, albeit totally cheesy and corny, fact about Drew and  I – our first Derby together was when I knew he was the one.  I asked him as we were walking in if we could do this forever and we’ve been to ALMOST every Derby, and every Derby weekend, since. We only missed once for a wedding in Miami and that year, we went to Oaks and flew down to Florida on Derby day. Yes, we are crazy people who love Derby more than Christmas.

It’s one of the only days of the year where we can abandon most of our daily responsibilities – kids, work, more kids – and just have fun. This once-a-year carefree attitude has earned him the nickname ‘Derby Drew.’ Not sure where it came from but it’s stuck and just like Santa Claus, he only makes an appearance once a year.

In honor of our favorite day of the year and his blog debut, I thought I’d let Drew do most of the talking and give some of his Derby tips. So without further ado, here’s 20 Questions with Derby Drew.

{Note: After going through these with him, I realize Derby Drew clearly hasn’t flipped the switch for the season yet so I had to throw in some notes which are all in italics.}

  1. When was your first Derby?
    I don’t even know. Probably the infield when I was in high school so probably ’98 or ’99.
  2. Do you remember who won? More importantly, do you remember any of that day?
    Nope and nope.
  3. What makes Derby different than any other sporting event?
    The atmosphere. It’s kind of electric with the booze and the colors and the gambling. It’s like a classy tailgate.
  4. Why do you go to Derby every year (don’t say because I drag you)?
    It’s part of being a Kentuckiana, it’s tradition.
  5. Favorite Derby week event?
    I kinda like the Parade. {Yes, that was a surprise to me too. Nothing against the Parade but really? I don’t think he’s been asan adult.} I don’t really go but I like to watch it on TV. And it always lets me know that Derby is two days away. I was in it once. That’s a story for a different day though {okayyyyy…}.
  6. What’s your favorite Derby tradition?
    It’s probably two-fold. The cliche answer is ‘My Old Kentucky’ home right before the Derby but my favorite thing we used to do was go to Ben’s {his best friend} Aunt Judy’s house to pre-party and sing Christmas songs. I think we need to do that again this year. {Agreed. More on the backstory of this very random tradition in this post}
  7. What’s your first stop when you get to Churchill Downs?
    To buy a program or a Mint Julep, or both.
  8. What should a first-timer do at the track?
    Go to the infield. Make a bet. Have a Mint Julep. Not necessarily all at once but bonus points if you do.
  9. Infield or clubhouse?
    I think there’s an evolution. Younger me would for sure say infield but I don’t think I can hang anymore. So now it’s definitely clubhouse. But I’d always be down to try again.
  10. Most ridiculous Derby memory?
    I mean, it’s hard to pick just one. Last year I went on a knee scooter in the rain. {He tore his achilles tendon three weeks before Derby which ended up being mildly helpful, we got to skip most lines.}Or the year we made it up to 5th Floor for the Derby race.  {There used to be a dining room area there which doesn’t exist anymore, I think it’s where the Finish Line Suites are now. We started in the Paddock, in the rain. Somehow, last minute, we got invited by a random work contact up to a fancy area where we had no business being after a day with the herd in the Paddock. Drew spent the entire time trying to talk the cops into letting him into Michael Jordan’s party in the room next door.}

On Drew: Vineyard Vines Seersucker Blazer
Iced Mint Julep Breaker Pants | Kentucky Derby Helmets Jockey Tie
Cole Haan Original Grand Wingtip Oxford
On Me: Vineyard Vines Off the Shoulder Run for the Roses Dress 
Fascinate Designs Fascinator


Derby Accessories

11. How do you pick your Derby outfit?
I usually have you do it.

12. Do you think you should coordinate with your date or do your own thing?
I think you should do whatever your date tells you to do.

13. What tips would you give guys coming to Derby for the first time when picking their outfits?
{At this point, Drew and I have a breakdown over his inability to provide any sort of valuable answers… next question}

14. Any other tips when it comes to Derby? i.e buying tickets, getting to the track, making bets?
I would make sure you know how you’re getting to and from the track. And if you’re Uber-ing you need to know where the drop-off/pick-up is. Remember that time I got into a fight with a taxi driver? Yeah, you can’t do that. Hire a driver. {Pro tip: We have a college kid that drives us all weekend and it is PERFECTION.}

15. Any Derby don’ts?
Don’t run out of cash. Bring plenty of cash because the ATMs tend to run out of money towards the end of the day.

Derby Looks for Guys


16. How do you pick your Derby horse?
I listen to what the more knowledgeable people say and try to bet what they do. But let’s be honest, we don’t normally have one horse. We normally have like a dozen Derby bets. {It’s true. We usually have an enormous pile of tickets.}

17. Favorite Kind of Bet?
I’m a big exacta box and superfecta guy. I also like the Derby Day Pick 6. {Where you try to pick the winners in six consecutive races.} Oh, and do a Show bet with your group. Everyone throws in $20 and you keep doing Show bets with the winnings and see how long you can keep it going.

18. What should you bring with you to the track?
Obviously your phone but make sure to download the Twin Spires app before you get there so you can bet on your phone instead of standing in long lines every race. Plus, if you run out of cash, you’ll still be able to bet.

19. On a scale of 1 to 10 how embarrassed are you by me at the Derby?
Oh I thought you were going to say about this post. Um… probably like a 5. ‘Cause by the time Derby hits I’ve already had a full week with you where you’re super extra, so by Saturday, I’m pretty used to it. As long as you don’t ask me to take a lot of pictures then I’m not super annoyed.

20. Can we go to Derby every year?  Yes.

Derby Dresses
Rapid Fire

Oaks or Derby? Derby

Party the Night Before or the Night After the Race? Night Before cause then you just get up and keep it going.

Mint Julep or Budweiser? Mint Julep

Exacta or Trifecta? Exacta

Bow Tie or Necktie? Bowtie but not for looks but because when you’re at the track, your tie doesn’t hang down and get in your way when you’re reading the program or eating or making bets.

Prints or Bright Colors? Both.

Fascinators or Hats? Fascinators as long as the feathers aren’t too big.

For guys, hat or no hat? I always like hats but have never worn one to Derby… yet.

2 Comments

  1. Reply

    Baili Taylor

    April 24, 2019

    Love love love this and you guys!

  2. Reply

    Kelly

    April 24, 2019

    Could not love this more!! Love the Derby Davis’❤️

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