You Can Sew It—But Can You Accessorize It? (The Joan Accessory Hunt)

Mad Men's Joan Holloway: Not a woman with accessory problems. (And yes, I know she wears pointier shoes than that, but those are shoes I actually own, so: close enough.)

So, tell me: am I the only sewist who is excellent at coordinating colors and textures and prints to produce an adorable outfit... and woefully uninspired when it comes to accessorizing said adorable outfit?

Which is a problem, since accessories can take your look to a whole other level of awesome... or totally destroy it.

Especially with something like my Mad Men challenge dress. Joan is not a slapdash accessorizer--unlike me, she is all about a total, polished look. So the above is a rough sketch of how I plan to achieve...

The classic Joan accessories:

1. A gold-tone pen necklace. Found easily via 1928 jewelry.
2. An elegant gold-tone brooch. I considered one very similar to hers, but this lovely Corocraft double leaf brooch I saw at the Today's Vintage booth at the Brooklyn Flea market yesterday just called out to me. And it was $10. Sold! (And now the first and only brooch I own).
   
3. Elegant earrings. I believe she's wearing pearl studs in the above. I already have a pair (wore them for my wedding and job interviews), so DONE.
4. A classic frame-style handbag. I couldn't find any on Polyvore (and they don't let you clip from Etsy or Flickr), but here's one from Etsy that is very Joan...
   

   Source: etsy.com via Mikhaela on Pinterest

   
   ... though I'm not actually going to buy this particular one. I may just go with a structured eggplant-colored leather tote I already own (from DSW clearance years ago) as "close enough."
5. Pointy-toed pumps. Authentic or not, I just do not DO pointy toes or spiky heels. The above shoes--Tsubo Eeini pumps in "nude" with a sturdy low heel--are the closest I get.
6. A self-fabric belt. I'm making a self-fabric bow belt to go with my dress, so DONE. (or will be done).

But anyway: back to my usual accessory struggles. It's really rather sad. I'll spend twenty minutes carefully composing a coordinated clash of dots and stripes... and a moment or less on choosing a scarf or a bag to set it off. I don't even own a properly fitting sunhat (and I'm corpse-pale enough to REALLY REALLY need one). And when it comes to coordinating bags and shoes? And mixing or not mixing black and brown leather and gold and silver tone jewelry or... ARGH.

As Exhibit A, I present...

The boring accessories I wore EVERY DAY in college, even with dresses:

• Earrings: A pair of sterling silver hoop earrings from the ear-piercing store. (I'm still wearing these. Almost every day. Could I have more boring ears?!)
• Necklace: A thin barely noticeable delicate-looking necklace with a charm on it.
• Scarf: None ever. (not counting winter scarves, obviously).
• Belt: Also none ever.
• Shoes: Doc Martens boots. With a steel toe. (I got into this habit while working in a shipping hub at UPS in order to protect my toes. It wasn't until I stopped wearing these constantly that I realized how freaking HEAVY they were. Ouch!)
• Bag: A backpack. The day hiking kind, not the fancy kind.
• Watch: Digital. The running kind. Except I wasn't a runner. (It's hard in steel-toed boots).
• Hats, brooches, pins, hair accessories, other miscellanea: Ha ha ha ha.

Now, don't get me wrong. There are some...

Accessories I totally GET now:

• Glasses. I love my glasses. I have two pairs that fit--one brown, one bright green--and I should probably match them to my outfits better, but whatever. Hurrah for cute spectacles! My current favorites are these cat-eye Bevel brand glasses, mine are bright green:
  

  Source: contactsandspecs.com via Mikhaela on Pinterest

• Shoes. Over the past seven years I have carefully curated a very small collection of comfortable yet cute retro-influenced flats, heels, boots and sandals with round toes and sturdy, low heels (if any). Go me! I do need to clean out some shoes I have worn past all repair, but it's generally in good shape. These Miz Mooz lovelies (which I'm wearing today) are a good example:
  
  
  
  Miz Mooz pumps
• Necklaces. The brighter the better:
  

  I keep mine on a set of pegs on the wall and admire them daily. And I'm trying to gradually replace the cheap bright plastic Forever 21 costume jewelry necklaces like the above with equally inexpensive but much fancier looking bright vintage costume jewelry necklaces.

But there are many more...

Accessories on which I continue to be clueless:

• Scarves. Own a bunch, even some vintage silk ones, but no idea when/how to add or how to tie them. I need to play with this. Somehow I always feel like instead of making things more fun, they make me look frumpier/older.
• Belts. Considering how much I love working the whole hourglass silhouette, I own/wear hardly any, mostly the cheapo pleather kind with the big round buckle.
• Hats. I have a huge head and finding hats that fit--never mind hats I actually like--is a challenge. So I have one ugly sunhat that pinches my head. Maybe I could make some (at least the breezy simple cotton kind). The only winter hats I have are self-knit.
• Bags. My husband frequently asks me when I'm going to stop lugging around a gigantic bag that can swallow the universe, because he worries I am hurting my back. He has a point. My mom got me a giant Brooklyn Industries bag--similar to this one:
  

  ...but brighter with a magenta print--when I needed to carry a breast pump to and fro from work. I hung up the pump horns months ago, but I'm still lugging the bag (now with the sweater I'm knitting inside), and I don't have a smaller bag for more casual occasions or running about on the weekends. I literally carry this suitcase-sized bag EVERYWHERE. It makes no sense and I must stop.

• Earrings. Yeah, still wearing the tiny hoops I got from the ear-piercing studio. In 1990-something. Every day. Ok then!
• Watches. I wear the same casual black leather-strapped watch. Every day. But it least it has a traditional, not digital, face, and nice typography.
• Rings. I wear my wedding ring. That's it!
• Brooches/Hatpins/Hair Accessories/Misc.. Er...

But whatever. There's no time like the present to start playing around with and exploring these things, and this Mad Men challenge is a great opportunity for that!

So, readers: are you an accessorizing superhero, or a accessorizing slacker? Are you better with some items than others? And is all this stressing over accessories just totally unnecessary and far too much work? Please confess!

P.S. Also--what do you think of my Joan accessory plans? Is the pen necklace fun, or too cliched/costume-y/obvious?