Kentucky Derby Plus Size Vintage Style Outfit Ideas

Plus Size Pin Up Style Kentucky Derby Day Outfit with Beautiful Purple Fascinator

plus size pin up style kentucky derby outfit and accessories including gloves and fascinator


I Love Dressing Up for Kentucky Derby!


For an Accessories Czarina such as myself, Kentucky Derby Day is like a second Christmas -- or maybe a third Halloween -- Mardi Gras being the second one? Haha. Anyway, what I'm saying is, when the point is to dress up in clothes you normally wouldn't wear, in a fancy outfit, sign me up! I even wore little gloves with my rings over them, all Hollywood Glamour style. 

My Plus Size Pinup Style Kentucky Derby Outfit in Green and Purple


plus size pin up kentucky derby outfit of the day with 1950s style swing skirt and purple fascinator

I'm depressed that the whole outfit came out so blurry but it is really hard to use a smart phone while wearing fancy gloves. And the Uber was on its way so I didn't have much time to pose for myself. But as you can see, I chose green, black and purple as my outfit colors for the Derby watch party I went to. The emerald green swing skirt dress is from SammyDress.com. 

purple and black accessories for Kentucky Derby outfit including shirt black gloves and purple fascinator

Accessories Are the Key to a Fantastic Kentuck Derby Outfit


This gorgeous fascinator was a gift from my mom for my birthday a few years ago. I've worn it to a wedding and a bachelorette party. And I've lent it out for Derby Parties to others in the past years. This was my first time wearing it for Derby Day. I want an excuse to wear it everyday though. Haha. Though it's like chocolate ganache. Use sparingly so it doesn't lose it's special-ness. I have no idea where these cloves came from, but I think they might have belonged to my great aunt Betty. On a day like Derby Day, it's okay to go a bit overboard on accessories. That's why I'm wearing earrings and a necklace and a facinator and gloves and rings over the gloves. Not my usual MO. It all works, though, if you stay with the same color and add things in neutral colors in addition.


1950s Style Vintage Style Plus Size Pin Up Kentucky Derby Outfit Details


  • Swing skirt emerald green dress - SammyDress.com, $10
  • Purple cardigan - Target, $10
  • Fascinator - gift from shop in New Orleans
  • Purple chandelier earrings - gift
  • Purple beaded choer necklace - gift
  • Black belt with gold clasp - H&M, $8
  • Short black faux silk gloves - hand-me-down
  • Quartz cocktail ring - Old Navy, $10
  • Beaded bracelet - gift
  • Stockings - CVS, $6


Yikes! Looks like my advice for a snazzy outfit is to get really beautiful accessories from friends and family as gifts? Time like this, when I see how many nice things I have given to me by others, I really am so very lucky to have such thoughtful people in my life! Love!!!