Halloween Costuming...Preppy style

Lately I've been thinking of Halloween.... not a big ole' surprise, surprise eh during this month of October? But costuming, and what we choose to costume ourselves with, has been on my mind since running across the above photo of my husband and I dressed-up for a Halloween Ball the month we first began dating back in 1989. (We're standing in the hallway of my college dorm)

We could have gone to the festivities as I guess just about anything and once at the dance, it was glaringly obvious that most party-goers had come in about the wildest formations of "anything" they could muster. However, being both raised-Preppy, James and I 1.) sought Anglophile and historic inspiration, 2.) found the best class of costume to be had around town and 3.) coordinated our theme and so... I was the "Lady in the Tower" of London and James but of course was the Beefeater Guard of said tower ;)

This past April we enjoyed touring around the actual Tower of London together which was a blast and being there kinda' brought us full-circle to the theme of many a Halloween ago.

For my 40th Birthday blow-out-bash a few years back, we again coordinated our costuming efforts. This time, since we live out on a small island, we went for a local-flavor theme that had me dressing as a Mermaid and James simply gearing-up in his flyfishing apparel. That evening was such a fun celebration with the house literally packed-full of folks and our good friend Don "won" the best costume award with his quite amazing Don Juan impersonation: cape, sword, black mask, clothing n' tall boots and an attitude to match. He was hilarious!

SO in the spirit of Halloween and all-things-Preppy, here's a listing of Prep and Non-Prep Halloween attire to get a laugh out of and perhaps even some costuming inspiration from:

Prep Costume: going as a rendition of the family gardener complete with muddied Wellie boots

Non-Prep Costume: going as Larry the Cable Guy

Prep Costume: any Royal entity or actual personage... purple, ermine and crown is optional

Non-Prep: any current Hollywood "star" especially if the face is some full-head rubber mask

Prep Costume: a classic Vampire, Witch or Ghost

Non-Prep: Freddy Kruger, Jason, Michael Myers or any other low-budget film slasher

Prep Costume: one's mother's old Lilly Pulitzer maxi-gown aka Palm Beach circa 1970's

Non-Prep: doing the hobo-look because one has not thought of a decent costume in time

Prep Costume: Polo playing or English Riding togs

Non-Prep: Bowling League shirt and empty bowling ball bag carried for potential candy bounty

Prep Costume: looking subtely-sexy in a non-sexy costume

Non-Prep: those unfortunate tarty servitude French Maid, Pirate Wench and the like outfits

Prep Costume: classic Devil or Angel

Non-Prep: politician masks donned with an ill-fitting business suit

Prep Costume winner: dressing like-Daddy-does in a smoking jacket, leather slippers, pipe, etc.

Prep Costume loser: dressing like anyone Daddy or Mother hires including accountants, bankers

Hope you enjoyed a good tongue-in-cheek chuckle and Happy Halloween costuming to you all coming up!