Recreating Christmas Caroling Costumes through the Ages: Part II

Getting in the Christmas Spirit!


This article is a continuation of Christmas Caroling Through Time: From Fur Capes to Fistfights
and is Part 2 of Recreating Christmas Caroling Costumes through the Ages

If you want to step out of the norm and take on the adventure of caroling, there are three fabulous eras to costume from: ye olde Middle Ages, the classic mid-19th Century, and the rootin’ tootin’ 1950s. Each era has it’s advantages (warmth, thank goodness!) and challenges, but all of them are so much more fun than just parading around in your reindeer sweatpants.

If the Middle Ages seems a bit to “out there” and dealing with hoop skirts just makes you scrooge, then the 1950s Christmas Caroler may be right up your alley! With the surge in vintage clothing awareness lately, finding period or period-inspired 1950s pieces is easier than instant cocoa! The hardest part is deciding what color of pumps best match your dress. The 1950s caroler doesn’t even have to venture outside. Instead, she can be chauffeured by swanky automobile to her friend’s house for a dinner party in front of the fire. Put on some swinging Christmas records or gather around the piano and carol until the eggnog runs out!

A Christmas Special: 1950s

Dress or sweater/skirt combo
Stockings or tights
Pumps, oxford, or loafers
Coats, gloves and hats
Funky Christmas jewelry or accessories (optional, but highly recommended)

Go Green! (and Gold)

Vintage by FabGabs


Vintage by 4birdsvintage


Vintage by RococoVintage


Vintage by wildfellhallvintage


Vintage by TANGLeAndFoLd


Vintage by junquedujour


Outshine Rudolph!

Vintage by YeOldeAntiqueShoppe


Vintage by WearAreTheyNow


Vintage by KaytoesVintage


Vintage by gogovintage


Vintage by MissMartys


Vintage by OnlyFlowers3438


Vintage by Sweetbeefinds


Be a Snow Angel!

Vintage by RococoVintage


Vintage by jessamity


Vintage by vixenandvelocity


Vintage by swingkatsvintage


Vintage by dreamwyldevintage


Vintage by DalenaVintage



On Trend: 1950s Fun and Games!

Snow Sports

If you want to spread the 1950s Christmas spirit by caroling from door to door, ladies can opt for some ankle boots or loafers. You can also take your 1950s party around the neighborhood on cross-country skis. Other winter sports like skating and snow man building contests were all the rage.

Vintage by CarnivoreCockatiel


Tropical Holidays

The 1950s also saw the rise of the tropical island paradise theme, with Hawaiian Christmas music joining in the island mania! If you live where palm trees grow and it never snows, then the 1950s Christmas caroler is perfect for you. All things Hawaiian were in style, from Christmas cards with hula dancers to girls wearing Santa hats with their bikinis (perfect for you pin-up lovers)!

Vintage by alexsandras



Tips and Tricks:

The 1950s silhouette varied widely, from pants to skirts to gowns. If you want a quick, easy outfit, you can’t go wrong with a simple turtle neck, button-up sweater, and a knee-length flared skirt! If dresses aren’t your thing, try some high-waited, festive plaid slacks and a tucked-in, crisp silk shirt accented with a kitschy brooch.

Want to look authentic? Here are some classic Cuban-heel stockings with the sexy black seam up the back!

5 thoughts on “Recreating Christmas Caroling Costumes through the Ages: Part II

  1. This is great…makes me want to go caroling (after stocking up on clothes, of course). I especially love the full skirts & long sleeves…although being in Florida I might be better off with the bathing suit & Santa hat combo.

    Thanks so much for including my red heels!

  2. I’m just seeing this! Thanks for including my vintage earrings here! I’m in love with all the dresses you chose! That green one especially. Wowie!
    Vixen & Velocity Vintage

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