Anachronistic Dressing: A Tribute to the Past or an Insult to its Memory?

When one becomes accustomed to incorporating vintage items into his or her daily wardrobe, the question may soon arise as to whether or not pieces from different eras can be harmoniously matched and work together in one outfit. I used to flat out reject the notion of combining clothing from multiple generations... I shudder at the images burned into my brain of this attempt done wrong, like combining an adorable 50's housedress with 80's doc martins,

or a 70's hippie look with a chic roaring 20's hat.

Of course this is all subjective; who knows, maybe someone out there is pulling these combinations off as we speak, or Vogue may declare these looks IN next season and before I know it I'll find myself perpetrating these historical crimes that I now denounce. But fashion forecasts aside, lately I have been observing that mixing eras doesn't have to look confused and awkward, but can be a tribute to multiple moments in the past contained in one ensemble... when done right, that is.

Check out Regan from one of my favorite blogs La Meow combining 20's flapper with 70's punk.
Total badass anachronistic perfection.

The real question is, Why does Regan look so perfect whereas others just look poorly put together? What makes anachronistic dressing work, and what makes it fail? Regan suggested that her look worked because it's combining two rebellious movements in fashion.

Me and my roommate Jackie decided to throw together some anachronistic outfits of our own and have a little photoshoot to explore this conundrum. Did we succeed, or shall we be forever inducted into the historical nightmare hall of fame?

Here is my first attempt at combining eras. The hair is inspired by the 60's, the bow tie and blouse by 40's school girl, the ankle boots are from the 80's, the clutch is inspired by turn of the century tapestry bags, and the skinny jeans are modern!

Lace headband: Homemade

Blouse and clutch: thrifted

Bow tie: Antique store

Jeans: Urban Outfitters

Pink pixie ankle boots: Vintage 80's, found in Cincinnati

Jackie went eightiestastic with the gigantic sheep shirt and matching hair, but her spectator pumps are inspired by the ones that came out in the 40's though I doubt these particular ones are that old (I could be wrong, correct me if I am), her long necklace is 20's inspired, and her shorts-tights combo is distinctly contemporary.

Oversized sheep shirt: Vintage 80's, a gift from her friends' mom

Spectator pumps: thrifted

Jewelry and clutch: thrifted (?)

My next attempt combined some 70's high waisted jeans, turn of the century edwardian inspired blouse that buttons to neck with a ribbon tie, a fedora from the 20s, 80's green pumps, and a D&G bag that was popular over the summer (total knockoff btw!).

Fedora: Vintage from the 20's, found at a garage sale years ago.

Blouse: The Limited, hand me down from sister long ago before I outgrew her!

Jeans: Vintage 70's, found in Austin

Pumps: Thrifted

Dolce&Gabbana knockoff: some undisclosed street corner, of course.

And for her final historical hodgepodge, Jackie had 80's hair, a 20's inspired silk dress with 20's inspired long necklace, vintage pirate boots from the 70's, and a leopard print bracelet which I will mark as contemporary-- she made it herself out of a broken earring!

Dress: Urban Outfitters

Necklace: Thrifted

Pirate boots: Vintage 70's, found in Austin last year.

Animal print bracelet: Homemade.

I think we did a pretty good job! I think the truth is that fashion goes through so many cycles that in our day and age it's not unusual to see inspirations from different eras subtly paired. Perhaps the faux-pas occurs when too many distinctive pieces are competing for focus. In the movies and SciFi books, they always warn against playing with time-travel, but me and Jackie had a good time breaking this rule-- arguably too good of a time...