The Road to the Kentucky Derby is heating up, and if you’re planning on attending one of the major prep races (or just want to spend a day at the track in style) we have some looks perfect for the occasion. You can shop each look by clicking on the item you like, and no item in any set costs more than $55. Ready? Let’s hit it!
16MenSpring_01 by penelopemiller featuring mens shoes
Lands' End mens slim pantslandsend.com
Men's socksuniqlo.com
Steve Madden mens shoesstevemadden.com
Saddlebred mens short sleeve dress shirtbelk.com
Slim fit blazerhm.com
100% Silk Yellow Equestrian Horse Blanket Horse Racing Necktie Tie...smile.amazon.com
Our first look is perfect for an afternoon at one of the Southern racetracks, like Keeneland, Turfway Park or Oaklawn Park. Bright pants and ties are the de rigueur for Southern racing; that’s why we started with this pair of eye-catching bottoms from Land’s End for $49, then added a pink Saddlebred button-down for $20 and a bright yellow horse racing themed tie from Simple Luxuries for $39.95. Add a $50 blazer from H&M, a pair of comfortable but stylish shoes for $24 by Steve Madden, and a pair of simple striped socks for $4.30 by Uniqlo.
16MenSpring_02 by penelopemiller featuring mens tortoise shell sunglasses
Saks Fifth Avenue mens linen pantssaksoff5th.com
River Island mens cashmere socksriverisland.com
Dr. Scholl's mens oxford shoesshoebuy.com
Swiss Legend mens watchbluefly.com
Brooks Brothers mens long sleeve shirtgilt.com
Mens tortoise shell sunglasseskarmaloop.com
Bow tiesmile.amazon.com
Haspel Modern Fit Tan And White Striped Seersucker Two Button...smile.amazon.com
If you’re heading somewhere hot to go racing, like Gulfstream Park near Miami or Fair Grounds in New Orleans, seersucker is going to be your best friend. This tan-and-white blazer, made from the breathable material, is $49 by Haspel. The blue Brooks Brothers shirt is $39, the $25 bow tie is from Notch, and the linen trousers are $25 by Saks Fifth Avenue BLUE. The classic pair of wingtips are $50 by Dr. Scholl's, the socks are $10 from River Island; and accessorize the outfit with a pair of $25 tortoise shell shades by MQ Sunglasses and a handsome watch for $50 by Swiss Legend.
16MenSpring_03 by penelopemiller featuring mens gold watches
Forever 21 mens socksforever21.com
Vans mens shoesvans.com
MN Watches mens gold watchkarmaloop.com
BLACK BROWN 1826 mens fitted shirtlordandtaylor.com
Jeanstopman.com
Shengweiao Men's Zip Knitted Cardigan Sweater at Amazon Men’s Clothing...smile.amazon.com
If you’re heading to the Wood Memorial at Aqueduct in New York City, you may want to keep it casual – and warm! Start with a pair of dark-wash jeans like these for $50 from TopMan. The gingham shirt is $20 from Black Brown 1826, the sneakers are $45 by the ever-stylish Vans, and the socks are $5.99 from Forever21. Throw on a watch ($32, MN Watches), a horse racing-themed baseball cap ($25, AllPro Stores) and layer on a chunky sweater ($34, Shengweiao) to keep toasty.
16MenSpring_04 by penelopemiller featuring mens boat shoes
French Connection men s sportcoatusa.frenchconnection.com
Tommy Hilfiger mens boat shoesbelk.com
Mens watchamazon.com
Neiman Marcus mens dress shirtlastcall.com
Mens aviator sunglassespopmap.com
H&M chinos pantshm.com
Win, Place, Show Butterfly Bow Tieties.com
Santa Anita Program Kentucky Derby California Chrome Signed by Victor...ebay.com
Want to go to Santa Anita Park for April 9’s Santa Anita Derby? Be stylish and comfortable in a lightweight blue blazer for $50 by French Connection; add a $55 horse racing bow tie from Alynn Neckwear over a $45 Neiman Marcus white oxford shirt. The chinos are $35 by H&M, and the boat shoes are $32 by Tommy Hilfiger. The watch is just $20 by Xiaoya, and don’t forget a classic pair of aviators ($20, PopMap) to ward off the LA sun!