I go to the Kentucky Derby almost every year (the official Kentucky Derby style guide is my first stop each season). I bring my brother, Nate, and my partner. I style both of them, and I wear some pieces myself. I like color. I also hate sweat marks. So I test stuff. In sun. In crowds. With spilled mint juleps. Here’s what held up.
Why listen to me?
I wore a men’s seersucker jacket in size 36S. I wore the hat, the undershirt, and the sunglasses, all day. I also broke in the loafers at home. Nate wore the full suit and tie. I did the cleaning after. So, yeah, I lived with this gear.
The look that won the day
Short story? Linen plus seersucker plus a real hat. Not a cheap costume set.
- Jacket: Brooks Brothers seersucker jacket, blue-and-white stripe. Light. Air moves. It wrinkles, but it looks fine. I love it. I also kind of hate it. You’ll see why.
- Pants: J.Crew linen-cotton pants, light tan. Size 31 for Nate. They breathe. They don’t stick to legs when you sweat.
- Shirt: Mizzen+Main Leeward dress shirt, white. It’s stretchy and dries fast. I wore it under the jacket too. No stiff collar rash.
- Tie: Vineyard Vines bow tie, pink gingham. Cute. It kept its shape. But the neck strap scratched a little near 3 p.m. Small thing.
- Hat: Brixton Panama-style straw hat with a navy band. Shade matters. This one didn’t flop or pinch. I wore it and stole it back and forth with Nate.
- Shoes: Allen Edmonds Cavanaugh penny loafers, walnut. Classy, but they need a break-in week. I wore them with thick socks at home first.
- Socks: Bombas no-shows. They actually stayed put. Thank you, heel grips.
- Pocket square: Some cotton one I grabbed from J.Crew. White with a blue edge. It soaked up a splash of julep. Then saved the shirt. Smart little napkin.
Much of that palette came from browsing Penny Chic, which nails Derby-day color balance without veering into costume territory. I even published a deep dive on every item I tested—see the full breakdown in this full review.
You know what? That mix got compliments from strangers in line. Plus, the guys didn’t roast in the stands.
What didn’t work (and made me grumpy)
- Fast-fashion suits. We tried one from H&M. The shoulders puckered, and the seat ripped a little when Nate sat on the bleachers. It looked fine in photos, but felt cheap.
- Pure polyester shirts. Hot. Sticky. They trap smells. One hour in the sun and—whoa.
- Slim belts with shiny buckles. They dig in when you sit. Plus, they glare in photos.
- Flimsy straw hats. The wind near the paddock ate one. It folded like a taco.
Real-life Derby stuff no one tells you
- Security lines feel long. If your collar is tight, you’ll hate life. Leave a finger of space.
- Clear bag rules mean pockets matter. That’s why I like jackets with inside pockets. Tickets. Lip balm. Small sunscreen. Done.
- It’s humid. Your back will sweat. I wore a Uniqlo Airism v-neck under the dress shirt. It kept sweat off the outer fabric. Sounds odd, but it worked. I briefly considered some of the more extreme comfort hacks floating around—there's an honest review of adult cloth diapers that convinced me to stick with a good undershirt instead.
- Julep sugar stains. Cold water plus a Tide pen took it out of the pocket square and the shirt cuff.
If you roll into Louisville the night before the race and realize you still need a driver, last-minute tickets, or even someone to show you around, a quick browse of OneBackPage classifieds can connect you with locals offering services, rides, and other race-day essentials so you’re not scrambling on Derby morning.
Heading south after the race? Plenty of fans crash in nearby Clarksville to dodge Louisville hotel rates and soak up a lower-key bar scene. For up-to-the-minute local listings—everything from last-second room rentals to on-call massage therapists—check out the dedicated Clarksville board at OneNightAffair Bedpage Clarksville where the curated ads let you lock in a spot or service fast without wading through unrelated posts.
Seersucker love-hate
I love seersucker. I also hate it. Here’s the thing. It breathes and looks classic. But it wrinkles like a picnic blanket. After the race, the sleeves had deep bends at the elbow. Not gross—just lived-in. Steam fixed it fast. I hung the jacket in the bathroom while the shower ran hot. Ten minutes later, better.
Fit tips that saved us
- Tailor the waist. Even cheap pants look sharp when the waist fits. I took in Nate’s pants one inch. Cost was small. Look was big.
- Hem no break. A clean ankle helps loafers shine. Ask for a slight break or none.
- Collar comfort. If you do a bow tie, don’t choke the top button. A half size up in the neck can help, and the tie will hide it.
- Shoe break-in. Wear loafers with thick socks at home for three nights. Ten minutes each. No blisters on race day.
Budget vs. splurge picks I actually used
Budget-ish that didn’t flop:
- Uniqlo Airism v-neck underlayer
- J.Crew Factory cotton-linen pants
- Brixton straw hat (not the cheapest, still fair)
Splurge that felt worth it:
- Brooks Brothers seersucker jacket
- Allen Edmonds loafers
- Vineyard Vines bow tie (holds a knot, bright colors)
Skip:
- Polyester dress shirts
- Paper-thin straw hats
- Shiny belts
Care after the chaos
I spot-cleaned the lapel with cold water and a dab of Woolite. I let the jacket air on a wide hanger. Pants got a gentle wash in a mesh bag, then hung dry. The loafers got cedar shoe trees right away. They kept their shape and lost the smell. The hat? I brushed off dust with a soft brush and kept it on a shelf, not a hook.
One more tiny thing: color
Light blue suit, pink bow, tan shoes. That’s safe and sweet. If you want bolder, try a green linen jacket with a navy tie and white pants. Just pick one loud piece. Not all three. The crowd is a garden of pastels, so you can have fun. You don’t need clown bright.
If you're still hunting for inspiration, Town & Country put together a sharp visual guide to men's Kentucky Derby outfits that helped me refine these combos.
The verdict
If you’re dressing for Derby, go light and breezy. Linen or seersucker. Real straw hat. Loafers you have broken in. A bow tie if you like flair, or a knit tie if you want chill. Keep a pocket square handy for spills.
I’ll buy the same jacket again. I’ll keep the loafers. I’ll skip the cheap hats. And I’ll pack that small sunscreen every single time. Because sun on a white collar? Not cute. But a cool, comfy look that lasts all day? That’s the win.