Kentucky Derby Style feat. Michael Andrews

May 3rd, 2013

Derby season kicks off this Saturday in Kentucky.

Along with the Southern tradition of horse racing comes the equally exciting Southern tradition of dandy tailoring.

Michael Andrews is a Southern gentleman turned NYC bespoke clothier, so we couldn’t think of a better person to give us some ideas on how to dress for this weekend’s Derby (or Derby party).

    1. Fine Linens


    Derby style is all about lightweight tailoring (think linen and seersucker) in preppy Spring colors (like florals and pastels) finished-off with dandy accessories (like bowties and boater hats).

    So embrace your inner Southern gentleman and have some fun with it – this is one of those occasions when you can’t really be overdressed.


    A custom-made equestrian inspired scooter helmet is a nice touch too, you know, for those of us watching the derby on TV and cruising around the big city.


    Navy shoes are underrated.

    They have an appealing richness in the Spring/Summer and they work with just about everything – from conservative grey suit pants to preppy red chinos.

    Mike also has the perfect pant break to show these beauties off.


    2. Madras Man


    If there is ever a time to wear a madras jacket, it’s to celebrate a sporting event involving horses.

    The trick to pulling-off such a bold jacket is keeping the rest of the look simple. Mike rocks it with a white shirt, navy rep bowtie and light blue trousers.


    The hidden-placket shirt is a nice subtle touch, it keeps the look sharp and streamlined.


    Nothing says “watching a classic outdoor sporting event” like a pair of spectator wingtips.


    3. Not Your Father’s Seersucker


    Seersucker is the obvious choice come Derby weekend, so don’t expect to be the only guy at the party wearing the traditional ribbed stripes. One way to keep it fresh is to find it in an unexpected color (seersucker is a type of cotton fabric that comes in many colors, not just light blue/white).

    Or you could take it a step further and break out a two-tone micro-gingham seersucker, in which case, you’d be a boss.


    Looking to make a lightweight jacket look more “Spring/Summer”? Swap out the dark buttons for light tortoise or white (like all three of Mike’s jackets in this post).

    Michael is also great at mixing-and-matching his suit separates. For example, here he uses the waistcoat and trousers from a light navy Spring suit to anchor down the patterned seersucker jacket.

    And there’s that white hidden-placket tuxedo shirt again…probably the most versatile shirt a man can own.


    A light-medium brown loafer is a great choice for anchoring down colorful, lightweight tailoring.


    Thanks for reading.

    Yours in style,

    Dan Trepanier


    Photography by Alex Crawford

    • Edward

      I love this guy’s style.
      We love horse racing in the UK. The glamor, the pomp (as we call it), the tradition.
      The blissful swagger of being a true Southerner, says champion.
      Come race day, I could see this being being an incredible outfit. Tailoring, bright and sharp. Really like it, go daddy!

    • http://undefined Robert

      I do find this post rather unfair, as Michael’s closet is virtually a swatch book and a creative imagination. Remarkable none-the-less. Michael is a great guy and wish him and his company nothing but the best!

      • Dan Trepanier

        Unfair, eh? Don’t hate the player because he plays the game.

        • http://undefined Robert

          It’s my jealousness taking over..I strive to look as polished as Michael and co. I have recently had the pleasure of getting to know a few of the associates in the DC location. Couldn’t find a better group in this line of work.

    • Tom

      Questions for the style blogger: What other blogs influence this blog? What blogs/tumblrs do you think are presenting good content? Noticed that you don’t regularly credit or mention any other blogs in menswear.

    • Professor Black

      Look one is yummy.

    • Dylan Nie

      I have to say I must agree one of the other comment about the “Madras Man” look, the bow tie bothers me a bit. The pattern on the blazer is crazy enough, then adding the stripes on the bow tie takes the attention away from the blazer, so I think it would be much better to leave the bowtie off in this look. Other than that, I think the outfits are brilliantly put together!


    • The Promethean Man

      The linen blazer is crackin’ but I can’t handle the madras. It’s way too much for me, though I think it’d be easier to look at if you toss the bow tie and open up the shirt a little.

      Great post!


    • Theguybehindthelens

      The two tone micro gingham jacket in seersucker is too dope. Keep these killer posts coming guys.

    • Harrison

      Diggin’ the hidden placket shirt!

    • cam

      great post…I was at the oaks today and will be at the derby tomorrow (born and raised in louisville after all). of course no one there is dressed better than me thanks to you guys ;)

    • Miguel

      Fine outfits, specially the last one, the shoes are killing it.

    • Brady P

      Great looks all the way around, I’d expect nothing less from Mr Andrews. That last look is incredible… Subtle details that look very sharp, gingham seersucker, matching suit pants and vest, hidden placket shirt, etc. Just great.

    • http://undefined Robert

      The Seersucker jacket is my next purchase…making my next appointment now! No one can touch MAB right now, Alex, this is the definition of “killin it.”

    • Kiel

      Homie picks a pair of shoes! Dang!

    • Justin

      Wow, all three of these outfits are amazing. The buttons in number three are a great touch, I never would have noticed if you hadn’t pointed them out, but they really make a difference!

      I also like how this post teaches general advice on how to wear something that really stands out without being abrasive.

      Also the fits are fantastic, +9000 to his tailor!

    • Mr E

      I could swear the tie in look number one is a Liberty of London print because I own a similar (if not exact) one.

      Is there any way we can look into that?

      • http://undefined Robert

        I contacted the FBI. They put it on their priority list. ;)

    • Dub

      THE Michael Andrews, killing it. Of course everything is draped to perfection. Especially like the 3rd ‘fit.

    • Michael

      Love the light navy pants and vest in look 3. Sharp!