Advice In Style: Bag Lady Chic

I find it fascinating that what once is considered “ugly”, can suddenly (or more like gradually over time, but it often feels sudden) be in style and, well, attractive.  Trends are so interesting to watch.  It would be so funny to hop in a time machine in a normal outfit from today and see how someone in the, say, 1930’s would respond.  I think it would be quite amusing to hear what people from other eras had to say about today’s sense of style!

Years ago I remember being in Starbucks with my dad, and in typical “dad” fashion, he felt the need to comment on the garb of the youth.  He said: “I can’t tell who’s homeless and who’s dressed like that on purpose!”  (does it get more DAD than that?)  And while that does sound like a super parent-y thing to say to your young daughter, I think he has a point!  There is most definitely a style happening that once belonged exclusively to what we would call a “bag lady”.  It can be sort of a derogatory term and is kind of reminiscent of “cat lady”.  Both have bad connotations, but at the same time, are kind of hip now.  I mean, when I was in high school, we would have cringed seeing someone with a cat on a knitted sweater or a girl wearing a thousand layers over baggy jeans.  It would have been a faux-pas-faux-sure.  (do you see what I did there?)  And yet now, this is not so.

Before we break down this style, we must give props to the originators of this style.  The girls who brought bag lady from the streets to the runways…Mary Kate and Ashley.

27086, LOS ANGELES, CALIFORNIA – Saturday 20th December 2008. A homeless looking Mary Kate Olsen awaits her driver after eating at Cafe Vida in the Pacific Palisades. Photograph: ©Gaz Shirley/PacificCoastNews.com

See what I’m talking about?  The caption even SAYS she looks homeless.  But how much you wanna bet that outfit cost, huh?  And there’s my point.  Bag lady is now chic.  I thought I’d give some tips on how to rock this style…some of them are more facetious than others, but you all know I kid because I love. :)

  1. Nothing should be your size.  If it is, you’re doing it wrong.  The key to this look is wearing EVERYTHING oversized.  That means you’re sizing up at least one to two sizes.  All kidding aside, the way to make this look GOOD and not like you just have no clue what size you are, is to pick things that are oversized but still flattering.  You’ll see Mary Kate and Ashley wearing a lot of thin drapey oversized dresses that hang on them large, but because they’re drapey, they don’t look like you’ve gained 10 pounds.  Thin fabrics are usually a good idea, or heavier knits that hang instead of stand up on their own, adding bulk.  Also, oversized structured jackets and sweaters can look chicer than baggy coats…however, the whole “giant puffy jacket” look is most definitely having a moment right now.
  2. Your jeans should be baggy enough to fit a diaper in the crotch.  Please don’t WEAR a diaper, but you catch my drift.  As in the previous point, if you get denim that’s soft enough, it will hang heavier on you and won’t look bulky.
  3. Structured shoes are a must.  If you wear this look with something casual like tennis shoes, it will be bag lady in the WRONG way.  So loafers, heels, booties, and scrappy sandals will be your friend with this look.  It’s all in the details.
  4. Don’t go too crazy on the jewelry.  This look is all about the mass amount of clothing you’re wearing and if you try to layer a ton of big jewelry, you WILL look like you’re just wearing everything in your closet.

Here’s my “bag lady chic” look.  I’ve got my favorite boyfriend Levi’s that sit lower on my waist because they’re a size too big, an oversized drapey vintage cami top, and my huge structured coat.  Structured shoes and simpl(er) jewelry make it not TOO crazy.

Some people really don’t like to wear this look.  I understand that.  It’s not the most flattering or slimming, but it sure does FEEL cool to rock!  If you’re feeling shy about it, you can always simplify it a little and wear skinny jeans instead of the boyfriend baggy fit…that might help you not feel SO oversized!  It’s all about finding the way that YOU like to wear a trend, not how other people wear it!
Happy bag lady-ing
Katy