Dressing for the Kentucky Derby: each year it brings up a lot of questions. We can confidently say we are experts on this topic: Crittenden has been dressing gentlemen for Derby, Keeneland, Ascot and the racing circuit for over 20 years, and we are on the ground in thoroughbred country, in charming MIdway and our new Louisville location. During racing season, we've got guys lined up in the morning waiting to get their tie, jacket, pocket square--let us walk you through it, too.
We'll tell you what we told a reporter from GQ this week who called for tips on dressing for the Derby, as always, our top takeaways are fabric and fit above all.
- Dress for the weather
- Make sure your clothes, shoes and hat fit
- Lighten up any look with a light colored trouser
- Go for it with your accessories (tastefully of course).
1) General Advice:
- Derby in Kentucky is really a holiday, so we look at it as dressing as you would for say, Easter or a spring wedding. It’s not enough to just throw on a sportcoat and tie and be done—Derby is a time for your inner dandy to shine (but always tastefully and we cannot emphasize enough —fit first. Take advantage of a local tailor or fine mens shop and make sure, your jacket especially, fits)
- The biggest issue locally is the weather is quite changeable in early May; it can be warm, but more commonly it’s chilly or rainy ~50-60 F. One Derby within memory it even snowed...
- So while everyone wants to dress colorfully and festively for Spring, we recommend thinking a bit more practically. We always offer a 50% wool, 50% linen fabric from England (our friends as Marling and Evans mill weave the most beautiful practical spring weight) in a couple of beautiful spring colors, as it provides a bit of warmth but is also breathable (our sport coats, based on one owned by the Duke of Windsor that our founder, menswear industry legend Critt Rawlings bought at auction at Sotheby’s, are French-faced (ie mostly unlined), so the jacket is light and comfortable.)
- For this reason we also don't really recommend seersucker for the first Sat in May (Derby Day), since seersucker as you know is truly meant to be worn in the height of summer heat (July/Aug) though its associated with the "Southern Gentleman” and so a lot of our out of town visitors do choose it for Derby. We do offer a traditional cotton seersucker, but also a woven in Italy wool seersucker which is more practical and great if you can find it (we are sold out for this year already). One interesting look is a solid unstriped seersucker—we’ve been selling alot of this fabric the past few years in navy or even a periwinkle blue—a bit more re-wearable for most guys but still feels like Derby.
- A heavier weight Irish linen in a DB or even an SB peak lapel in any color makes a great elegant look, and we always recommend a vest in our ivory silk and linen—the vest especially gives the elegant spring holiday/traditional look, very Kentucky gentleman.
- Our big tip is any sportcoat you have (no super 100’s suiting here guys) with a pair of ivory gabardine, silk & linen (our signature spring fabric) or even on a cooler day a cream flannel trouser =so elegant. Ivory trousers make any outfit more “spring.” Very "garden-party-at-Downton-Abbey" which is the look we are going for at Derby.
- One interesting thing is that Thoroughbred racing is an international circuit and we have owners/interests from the UK, Ireland, France, Japan and UAE at every Derby. So the dress, while not the top hat and morning suit required at Ascot, is similar in feel, and we dress many customers for Ascot also, as the same crowd is attending many of the big races (owners/trainers/breeders/syndicate guys etc.)
- At the Derby, and most races on the circuit, coat and tie are required and the dress code is pretty strict (ie they turn you away!) so for actually attending the races mixing with casual pieces wont work. But for guys who are going to Derby parties not at the track, sure—throw a light spring blazer over a tee shirt or a knit shirt or linen shirt, but we still recommend a trouser rather than a 5 pocket jean. A great way to dress up a more casual look but have Derby spirit is by throwing on a boutonniere! (Unless you’ve got a bespoke jacket you’ll have to have to open up your button hole with a tiny pair of scissors, like Swiss army knife size—we use a seam ripper—but its super old school old Hollywood and amazing to add a rose or a carnation—instant Derby elan).
2) Footwear: The ultimate Derby shoe is the spectator and we applaud any guy who goes this far as it’s a perfect time for that classic Spring shoe. However a tassel loafer, a Belgian loafer or a Stubbs and Wooten-type slipper are all also elegant but festive and popular choices. We strongly believe in quality first, and if your shoes fit you well, then thats where comfort comes in—make sure your shoes fit, and dont try to break in a new pair that day—wear them around a bit or choose a pair that are already broken in, but of course polished and well cared for. (Please unless you are very elderly, no white bottom-sneaker/dress shoe hybrids)
3) Accessories: Pocket square is mandatory—the easiest way to add elegance and make your look finished. Tie is necessary at the races, but for outside Derby parties you can do open collar with a colorful pocket square. If a guy is more conservative and wants to wear a navy or neutral color jacket, we suggest a pink or lavender striped, checked or plain dress shirt for a bit of lightness and color, plus pocket square (we sell beauties from France in linen and cotton, but any light color, festive pocket square is where you can add a little kitsch—equestrian theme silk pocket squares fly out the doors here each spring.) At Churchill Downs and Keeneland you will need a tie, and bow tie or regular tie is a purely personal choice. If a guy is bow-tie curious, the Derby is a perfect time to wear one! Lighter colors are best, but as long as it’s coordinated (but NOT matching) your tie and shirt color you are good.
4) Finally, hats. Traditionally Derby is great time to wear a hat, but of course this is not style 101 for most guys and great hats are harder and harder to find. This is where our tips about looking for quality (which does NOT have to be expensive but you may have to look around a bit—we recommend Meyer the Hatter in New Orleans, JJ Hats in NYC, and Cable Car Clothiers in San Francisco have a nice selection that they are known for.) We carry Panama hats, light, easy to coordinate with most spring looks, in the Spring that are popular and sell out fast. Again, fit is very important for hats. I think the idea of the cheesy fedora is because lots of guys are buying a hat that is too small or the brim is too small for their height, etc. The trilby is the hat we most commonly see that looks cheap and too small. However, if a guy is going for it with a hat a GOOD quality (again doesn’t have to cost a fortune—we sell beautiful made-in-Ecuador Panamas that retail for $125-135) and well-proportioned, medium brimmed Panama is our top rec for Derby. You will see a cowboy hat or two at the Derby, but we recommend the Panama, or if a guy is a big hat wearer and wants to invest in a quality fur-felt fedora, Homburg, or even a bowler (like a boss!) we applaud you-- Derby is the time to go for it (tastefully of course).
Our main takeaway is make sure your tailoring fits (get out and take advantage of the deep knowledge at your local tailor or mens tailoring shop!), dress for the weather, lighten up your look with a light trouser, and go for it with your accessories. Let’s see more boutonnieres out there this year!
Happy Derby ya'll!