Hey Sid!

The Derby

Hey Sid!

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"I'm making my first trek to the storied twin spires of Churchill Downs for the 2023 Kentucky Derby. Can you offer any advice on how to look great without overdoing things?” – Grant W.
Sid and Randall are both pictured standing in front of the colorful tie display in the Sid Mashburn Atlanta shop. Sid is holding a light blue poplin dress shirt, and Randall is holding the Wm Brown Bullseye Tie in Brown.

 neckwear is not optional

Hey Grant. I love this question.

We’ve dressed a looooot of people for the Kentucky Derby over the years. Most of them come in with exactly your perspective: “I want something with a little bit of pop… but I don’t want to go crazy.” And while I’ve never been myself, I know that this is a place where people do kind of go crazy… you’ll see all types. It’s kind of like Coachella for preppy people. So, yes, I hear you with not wanting to overdo things. 

If you’ve been reading this column for awhile, you know my lead singer theory of dressing – where you want to have one element of your look that’s your strongest piece, and everything else is singing backup. Good, quality voices that enhance the lead but don’t steal the show themselves. But if there were ever an appropriate occasion to sort of push the limits of this theory and get some more, let’s say, assertive backup vocals… it’s the Derby. It’s like that girl who sang on Dark Side of the Moon. This is the time to bring in the Clare Torry. Power vocals. 

But you still want to start with one piece as your anchor. Some guys dig a statement jacket, some guys like party pants. I’m in the second camp – I love a pair of colorful trousers. And some guys are most at home in a bright-as-heck bowtie. ESPECIALLY at the Derby. With that in mind, I went over to the Atlanta store and picked out a handful of outfits using a different lead singer from each category. I got some help from Randall, who’s been in the business forever and easily styled who knows how many outfits. Millions. I love his eye. So, depending on where you like to play things up, here are a few outfit ideas c/o me and Randall. We even invited Wm Brown.

When the jacket’s your lead: This jacket is really pretty. The creamy bone color in the ground keeps it from feeling too Eastery. Virgil No. 3 Jacket in Aegean/Forest Check Hopsack + Spread Collar Dress Shirt in Pink End-on-End + Silk Knit Tie in Hunter + Slim Straight Jean in White Garment-Dyed Denim + Italian Penny Loafer in Cigar Suede

When the suit’s your lead: Randall and I went back and forth on the neckwear piece for awhile, and you could make the case for the tie kinda stealing the mic here. I like how the highs and lows in the weave pull out the texture of the Prince of Wales check. Virgil No. 3 Suit in Brown/Bone/Orange Plaid Prince Of Wales Hopsack + Spread Collar Dress Shirt in Sky Awning Stripe Poplin + Linen Woven Tie in GreenItalian Tassel Loafer in Dark Chocolate Suede

When the shirt’s your lead: This was a surprising one… it shouldn’t work, but it does. It’s so easy to just go for a navy blazer but the Pacific blue color is actually perfect with this stripe. Spread Collar Dress Shirt in Orange/Pink/Blue Multi Stripe Poplin + Ghost Blazer in Pacific Wool Hopsack + Silk Club Tie in Brown Wm Brown Bullseye + Dress Trouser in Mid-Grey High-TwistHandsewn Penny Loafer in Chocolate Suede

When the pants are your lead: This one is the real Hall and Oates of the bunch. Granted, I’ve worn this jacket so many times that I tend to think of it as a neutral/backup piece. He and the pants are both pretty expressive, but they’re singing the same song. And I’m wearing a riff on this today, so… it’s like every day is the Derby. Garment-Dyed Field Chino in Grass Canvas + Virgil No. 2 Jacket in Chocolate/Bone Houndstooth + Spread Collar Dress Shirt in Sky End-On-End + Silk Knit Tie in Navy/French Blue DotItalian Penny Loafer in Chocolate Suede

When the bowtie’s your lead: I’m not a bowtie guy myself but if you are… again… this is the time. Go big. Silk Bow Tie in Light Blue Kinsey Stripe + Spread Collar Dress Shirt in Lavender Gingham Poplin + Ghost Blazer in Navy High-Twist + Slim Straight Jean in Natural DenimItalian Tassel Loafer in Cigar Suede

So there you go. Not a boater hat nor a seersucker suit to be found. But you will notice that every single one of those looks has some neckwear in it. I’ll say it: for the Derby, you need a jacket and you need a tie. Ann pushed back on this – she was like “are you sure you can’t wear a polo under a blazer? — and the answer is no, you cannot. Not for me. If you’re going to bet on the winner, you need to look like a winner. It is what it is. And then one last thing. For these looks, I was assuming you were starting from scratch… BUT if you’re working with vintage, I’d say the lead singer approach is a little more ironclad. If you have a pair of GTH Lilly pants from the 60s, keep the rest super simple… throw on a navy blazer and a white or blue shirt and call it a day. Same deal with a patchwork jacket… go for a solid blue shirt and khakis or blue jeans.

Okay, Grant. I hope you have fun on your maiden voyage to the Derby… and I hope you have fun with what you’re wearing. You’re going to see all sorts, and hopefully you’ll get a kick out of the outfits without feeling like you’re part of the parade. Oh, and my picks are Major Dude or Instant Coffee for the win. Enjoy.

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