Outfit Oops: What I Wore and Why It Didn't Work

This weekend, I had a bit of a dilemma. The lovely Frances from Polka Polish paid me a visit, and we had a great day of shopping and kvetching before taking a few photos for our respective blogs--and herein lay my dilemma. I don't like what I wore.

Frances looking adorable!
Photo courtesy of Polka Polish

In theory, this outfit ought to work-- it has texture, a focal point, and an unexpected fun piece-- but it just doesn't. And as I looked at the terrific photos Frances sent my way, I wondered, what should I do with beautiful photos of an outfit I don't like?

Photo courtesy of Polka Polish

It hit me that this is actually a great opportunity. It's always really inspiring to see gorgeous photos of outfits that work wonderfully-- they're great how-to's. But sometimes it can be useful, particularly when you're still trying to find your "look," to see gorgeous photos of an outfit that doesn't work: a "how-not-to," if you will. So, though I hope it won't be an often-occurring series, I thought I'd write a breakdown of a look that's just a little 'off,' and talk about why it doesn't work.  Besides, it's good for my vanity, and a reminder that hey, not everyone can bring their A game every day of the week!

So close!
Photo courtesy of Polka Polish

I think the impetus for this outfit came out of two things: the weather, which has been dreary despite technically being Spring, and an awareness of the balance of menswear/femme-wear I've been posting. It felt like I might be trending a little far on the tux/suit end of the spectrum, so I decided I'd femme it up a little by wearing a springtime skirt that, thanks to its silk makeup, has to be worn during the more brisk weeks of the season.  To keep the flowers as the focal point, I thought it'd be best to go with a cream shade on top, and to add texture, I decided on a cashmere sweater. Finally, since I felt I might look a fool wearing 100% springtime in 40-degree weather, and because I like mixing in unexpected elements, I added one of my favorite winter hats.

The result was almost-but-not-quite, and I think you can tell in my posture, it doesn't feel right.  Why?  Because these ideas work--for someone else.

I think there's three structural reasons it doesn't work on me:

1. Shape: 

Because I don't have an hourglass shape, wearing monochrome with no cinch at the waist actually padded out my waistline. It also flattened out my er, already small bust line. I think this is an important lesson in color blocking--it can be used to glide over trouble spots, or it can bring attention right to them. Use with care!

2. Shoes:

Wearing laced shoes with a longer skirt can sometimes make the already-short line of the leg look more fragmented, and this seems to be particularly true due to the pattern at the bottom of this skirt. Essentially, the shoes, combined with the single color from shoulders to hips, shortened and widened the figure. Ouch.

3. Hair:

Totally works in isolation! With everything else, though...Photo courtesy of Polka Polish

This is partly a mix of eras that doesn't work-- a 30s bob with a 50s skirt-- but I don't totally subscribe to single-era dressing.  I think the issue here, for me at least, is that a 30s bob is playing on androgyny, and the rest of my outfit is out-and-out femme. It makes for a slightly odd gender presentation. I've talked off and on about gender presentation, and how as a queer lady, wearing menswear or feminine dresses project very different messages about my identity. Since I feel somewhere towards the middle of the spectrum, I like to play with both styles, and I'm pretty comfortable with androgynous looks as well.  But for some reason I can't quite put my finger on, blending androgyny and femme doesn't work as well as femme/masculine or out-and-out androgyny.


The outfit I'm wearing here would be more ideally suited to someone with a fuller bust, slightly longer legs, and a looser wave set.  But body type and hair style aside, the outfit also totally conflicts with my own sense of style.

When I put this together, I thought a little too much about what I should present.  I thought I was being too androgynous, so I went femme, when really I'm much more comfortable wearing a blend of masculine and feminine.  So here is what I wish I'd worn:

As you can see, I stuck to my guns about the fur hat and floral skirt combo, and it's quirky, but I think it works. What I switched out were my shirt and shoes: I swapped the feminine cashmere for a more structured, collared shirt, and the laced shoes for heels that helped ground the blue stripes of the shirt.

A defined waistline and more spare detailing at the foot make a huge difference.

  Is it period-perfect? Well, no. But I think it's much more figure-flattering, thanks to the visible ribbon at the waist, and the vertical stripes that help elongate a more defined torso.  Basically, the top and bottom halves are balanced, rather than dragging attention from the shoulders straight down to the hem.

It seems paradoxical, but pairing the skirt with another pattern actually makes the florals pop more than they did against a neutral.

Comparing these two outfits, for me at least, teaches a great lesson about silhouette and styling. It also highlights one of the very most important rules of life and style: To thine own self be true. Wear what you like and what makes you feel good, and you'll look good.

Though I'd always prefer to demonstrate a look that works, I hope parsing out why something didn't work is helpful as you put together your own outfits.  And if and when I slip up again, I'll be sure to show you how and why!