Horse racing is SO much fun to watch. Growing up, my mom and dad would go to the Assiniboia Downs each year when we visited Winnipeg, Dad’s hometown. They would get all gussied up to go to a fancy dinner and bet on the horses. I remember the first time I got to go with them. It was right after high school graduation, and I was so excited to see the place I had heard so much about (and probably even more excited to order drinks because the drinking age was 18). We sat down to a delicious dinner overlooking the track, and Dad explained how the betting worked: win, place or show, exacta, trifecta, etc., He gave me $20 and told me to place my own bets. Mom and I would usually go by how much we liked the names of the horses, but Dad would be a little more methodical and choose the ones that actually had good odds of winning. It was such a fun atmosphere . . . people winning, losing, cheering their horses on. You couldn’t help but get caught up in the excitement. When the last race of the night came, Mom and I decided to pool our money to place a Trifecta bet (when you choose the selection of the first, second, and third place finishers in that exact order). A Trifecta is usually a long shot, but it can pay big if you win. So imagine our excitement when our horses came in first, then second, then third! In the right order! OMG! We had won, like $3,000? Maybe? We weren’t exactly sure how much, but it was a lot more than we had paid to make the bet. We were whooping and hollering and laughing — until — I realized what I had done. Maybe I got caught up in the excitement of things, or maybe (more likely) it was the 18-year-old drinking age, but when I had placed our bet, I mixed up the names of the horses. I had the right names but the wrong order. So our amazing win? That small bet that paid off big time? Didn’t really happen. On paper, at least. But hey — it makes for a good story 20 years later. (I’m still kicking myself.)
Mom hasn’t taken me back since (I don’t blame her), but we still watch the big races every year. My mom loves following the Triple Crown; I love an excuse to wear fancy hats and dresses. So when JCPenney asked us to take a look at their spring dresses, I was inspired to put together some fabulous outfit combinations in honor of this year’s upcoming Kentucky Derby (the first race of the Triple Crown). They have an amazing inventory of floral dresses and fancy hats, and the best bags, shoes and sunglasses to top it all off. It makes it super easy to put together a complete look that’s stylish and affordable. Win-win. (Unlike my betting.)
dress | shoes | hat | sunglasses | purse
Outfit Details
dress – Danny & Nicole Sleeveless Floral Fit & Flare Dress (wearing size 4), Super comfortable. I love that it accentuates my waist without being overly tight.
shoes – Qupid Women’s Amber Heeled Sandals, LOVE the floral accent — these are some fabulous statement shoes! (also in pink)
hat – Scala Solid Big Brim Derby Hat, The picture is a bit misleading . . . the actual hat has feathers and netting. Big and fancy!
sunglasses – US Polo Assn. Full Frame Sunglasses, These are like the quintessential oversize black sunglasses but for under $20 (also in tortoiseshell).
purse – Gunne Sax by Jessica McClintock Ivy Square Mesh Evening Bag, Wear with or without the chain strap, big enough for essentials but still small and dainty.
I had so much fun shopping for Derby looks that I couldn’t stop at just one, so here’s some more outfit inspiration — feel free to pin!
Derby Outfit Ideas: Dark Florals
This is the outfit I’m wearing in the pics. In the future, I can wear the dress dressed down with a denim jacket and flat sandals. The bag, sunglasses and shoes can all be worn on repeat with a bunch of different outfits. (LOVE the shoes.)
dress | shoes | hat | sunglasses | bag
Derby Outfit Idea: Peachy Keen
This hat is everything. I loved the color combination with this floral dress. The bag, shoes and sunnies are the perfect neutrals that can be worn again and again. (Bonus: you’ll have legs for days with those shoes.)
hat | bag | dress | sunglasses | shoes
Derby Outfit Idea: Pop of Red
I couldn’t resist this dress. I love the silhouette and the muted colors. Although you could wear this one with neutrals and let it be the star, I also loved adding the pops of red. Add lipstick and you’re good to go.
dress | hat | bag | shoes | sunglasses
XOXO,
Scotti
A huge thank you to JCPenney for sponsoring this post!! It was so much fun to put these looks together —great merchandise at a great value! As always, all product choices, thoughts, and opinions are my own. And readers, thank you for your continued support. It doesn’t go unnoticed, and is so very much appreciated!
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