How To Win A Costume Contest

I Like To Dress Up...

I’m not very competitive in regular life but there’s something about putting on an amazing, jaw-dropping costume that suddenly empowers every part of me. In that moment, I do feel like I am the best dressed ever and if anyone tries to get in the way of that then I’m fully prepared for my own live action reenactment of the waterhole scene from Mean Girls. What I’m trying to say is that I LOVE costumes, costume contests, and any reason to dress up. So, of course, I love winning them.


I’ve won four costume contests to date, six if you count spirit week from my high school days - I don’t because wow was that amateur hour. With each win, I can’t help but get a little more cocky. It’s kinda like my version of cocaine. Each win comes with it’s own high. It’s addictive. It’s exciting. ​

There was my first costume contest win even back on St. Patrick’s Day 2015. I went as the Irish Marie Antoinette. I dyed my Victorian wig green and painted a large kid’s princess costume I bought from Party City. I added gloves, makeup, and a cute little sign that said, “Let Them Eat Cake” except cake was crossed-out with “Get Drunk”. I didn’t dress up to win the costume contest, but I would by lying if I said I wasn’t 99% sure I wasn’t going to win going in.

​This party took place at Conroy’s outside of Boerne, Texas. The competition was mostly drunk men in their 40s who wore green polos and were trying to have an excuse not to go back home to their nagging wives. I remember being SO excited when I won the contest at the end. Hearing people yelling my name and begging for photos. I realized in that moment that costumes were pretty freakin’ cool. The owner of Conroy’s later tried to deny me the $300 bar tab I won because he “Didn’t remember me” from that night. So make sure to never visit Conroy’s trash bar next time you’re near San Antonio. Regardless of the post-party drama, this win was really what I needed at the time to gain more confidence.

The second costume contest I won basically by just showing up. I went to an Oscars watch party at this swanky rooftop bar, The J. Parker, in Chicago. It was me and a bunch of older ladies watching the Oscars and drinking champagne. It was incredibly fun, but nobody else even dressed up. So I won. It was fun, but the excitement wasn’t quite there. However, I did appreciate the $50 gift card. ​

My third costume contest win was in Salem, MA on Halloween. This party took place in the middle of Salem at the famous “Rockafellas” bar. This win of “Best dressed” was maybe the most impressive of all because people in Salem take Halloween very seriously. The competition was high. But, so was the thought I put into my costume. Wearing a wedding dress I bought on Craigslist for $50, my Catherine D’Lish dressing robe, and a custom $150 feather masquerade mask from New Orleans, I won “Best Dressed” Halloween 2017. It was a helluva time. ​

The last won was less of a formal "win". My mother and I dressed up as princesses to attend/watch the Royal Wedding of Prince Harry and Meghan Markle. We had a front row "seat" from our VIP window at Bluegrass BBQ across from Windsor Castle. We saw Prince Harry & Meghan in their horse-drawn carriage as they left their nuptials. It was an amazing, historic day. We were interviewed for our costumes by Brad Blanks of CBS Radio, Telemundo, and featured in TMZ. 

Tips To Winning A Costume Contest...

After all of these wins, a few losses, and just enjoying dressing up - I have gained a lot of knowledge in the costume contest world. I figured why not share what I’ve learned to help others *hopefully* win a contest they enter?! It's a blast to enter any competition, especially one where your imagination can run wild. So, here are my tips. Take ‘em or leave ‘em. ​

Don’t Do It For The Money

The biggest prize I ever won was a $300 bar tab. & that bar owner didn’t even give it to me. So you can’t do it for the money. You have to feel inspired by your costume, and whatever you win is just an added bonus. Plus, what you spend to make your costume will probably cost the same, if not more, than the prize value. However, no amount of money (okay, maybe some amount of money) can give you the confidence boost high upon hearing that your outfit won. 

Think Outside The Box

People want to see something creative. I have lost other costume contests before and while my outfit might have been amazing, that doesn’t necessarily mean it was creative. You need that “wow” factor. Try to picture a costume that no one has done before. Add something new to it. Make it your own.

Be A Social Butterfly

When it comes time to vote, you NEED people to like you and your outfit. Be a social butterfly. Talk to EVERYONE. & not just about your costume, I might add. Compliment their costumes. Befriend people. Toast with them, drink with them. Take photos. Be silly and fun. If everyone in that bar thinks you not only have a fun costume but also a fun personality, then you can honestly win wearing a trash bag. Contests, of any kind, demand popularity.

Arrive Early, Stay Late

You need to make sure you arrive early, as many parties or bars/restaurants pick contestants to qualify for the contest near the start of the event. Also, the earlier you arrive the more people you can meet and impress. ​Make sure to not only get to the party early but also to stay late. Don't leave as soon as the win is announced, rather you win or lose. Celebrating after the costume contest ends is a great way to enjoy your win, or to still have a fun time even if you didn't. 

Have fun!

Winning a costume contest is incredibly fun, rewarding, and exciting. However, if you don't win you should still try to have an amazing time. This is something I'm still working on, which is strange because as I mentioned earlier I don't normally feel too competitive. However, for some reason when I lose a costume contest I feel personally attacked. 

The truth is that dressing up and attending a party of any kind should be fun enough. You don't need to win in order to enjoy the moment. There will always be more costume contests to enter!