If yer going to spend yar hard earned doubloons, it best bet be on a high quality pirate or wench outfit.  There be two way to think about about costuming.  

1) Buy a different cheap costume every year 

2) Buy a great outfit that you can improve or change each year.

The average cost of a halloween costume be $96 for men n' $77 fer women, which can get costly over time.  Ye could buy a new costume each year, funneling money into a flimsy costume that will last ye a single night, or make an investment in an amazing outfit that ye be proud to wear n' will last ye years to come.

If yer going to spend $770-$960 on costumes over a ten year span, why not put that money towards a timeless outfit worth wearing again n' again?

Cheap Costume: You don't feel comfortable wearing it, it may fall apart before the night is done, it may not fit right, many other people can be wearing the same costume. 

Quality Outfit: A high quality costume will stand out from the crowd of cheap outfits. More people will ask for a photo.  You will feel like a movie star for a night.  Be part of the cool crowd.  You'll begin building a character that will grow with each year you wear it.

Popularity of Costuming:Costumes n' costumed celebrations have been a part of cultures all across the world throughout history.  Halloween, the most widespread costume holiday, hails from a Celtic Gaelic harvest festival with roots in Scotland, Ireland n' Wales.  Halloweens popularity has spread rapidly over the years, n' has become more popular in countries like Russia, Japan, Canada, Australia, Dubai, Saint Helena, n' most of Europe.  These celebrations aren't just fer kids either; the number of adults that participate in Halloween has grown from a little more than half in 2003 to over 70% in 2018.
Many countries have either adopted halloween or have their own cultural equivalent; this can be seen in countries n' regions like Mexico, Latin America, n' Spain, where people celebrate their loved ones during Dia de Los Muertos n' often have costumed celebrations.  

Outside of holidays, costumes have become a major draw to conventions.  Over the past 10 years cosplay has entered the spotlight as comic, anime, n' sci-fi conversions have grown from an underground niche to mainstream event.  

Why Pirates: In the past 10 years there have only been two costumes that has been consistently relevant enough to be listed within the top ten popular halloween costumes- Pirates n' Witches.  In addition to pirates 10 year reign as some of the most popular costumes, wenches made the listing fer 7 of the 10 years.

Part of what makes a pirate costume such a worthwhile investment is the sheer amount events ye can wear it to- its one costume that ye can wear more than once a year.  There be pirate festivals, Talk Like a Pirate Day celebrations, tall ship festivals, costume parties, Disney Cruises, Pirate Weekend at Renaissance Fairs, n' plenty of games fer sport teams who use pirates n' buccaneers as their mascot.

Pirates have a long history n' spanned across every country that touches the ocean, which allows for all sorts of different periods n' styles of garb.  This versatility allows for pirate costumes to be easily altered fer other events as well; with a little modification a classic pirate outfit could be styled as a colonial for 4th of July or Revolutionary War events.