Vintage/pinup fashionistas: what can I wear on my head with this dress?

August 4, 2015 6:15 PM

I am attending a company party where the theme is somewhere along the lines of "vintage Havana." The event will be held in the evening and there will be Cuban dancing, cigars, cocktails, etc. I bought this dress to wear to it but I am totally stumped about what to do to decorate my head as I am growing out a short haircut that is not salvageable on its own. More details inside.

I am currently growing my hair out from a pixie and it's in that awkward stage where basically the only thing I can do is pin back the bangs and sides. Trust me, I have tried curling it, faking some pinup girl bangs, finger waves, etc. and it's no bueno. Headbands on their own aren't enough. I think a hat or fascinator may be in order. Maaaaaaaybe a scarf that is artfully tied in a bow or something but I'd need VERY detailed picture/video instructions on how to achieve that and not look like I am appropriating religious headscarf culture.

Can you direct me to something that will be fabulous without looking costumey with this dress? Budget is $100ish. Please don't just say "a white cloche" because my imagination sucks. Photos or links to actual products please!

Also, please, no advice on styling my hair, as I am 99% sure it is just not going to work. I really think distraction via elaborate head-thing is the best option here.

Bonus points if you can direct me to a brick-and-mortar shop where I can buy in Portland OR this weekend or sometime in Seattle over the next week, or a website that will ship it to me within a week. Thank you!

posted by joan_holloway to Clothing, Beauty, & Fashion (28 answers total)

Is a wig an option? You can get a really nice wig for $100ish. This place has good reviews.
posted by juniperesque at 6:20 PM on August 4, 2015 [1 favorite]

40s tie up scarf. Detailed pictorial here scarf
posted by asockpuppet at 6:29 PM on August 4, 2015 [4 favorites]

The dress is what, 1950s era wiggle type? How about a humongous fake camellia on a comb behind your ear? Or a wide white brocade-covered headband, but even that is a little anachronistic, I think.
posted by chesty_a_arthur at 6:33 PM on August 4, 2015 [6 favorites]

Could you wing something with your bangs and do the 40s scarf thing with a fake ponytail/bun? Here's a youtube vid that shows how to tie the scarf.
posted by Klaxon Aoooogah at 6:34 PM on August 4, 2015

PS NO CLOCHE THAT IS 20S ARE YOU MAD
posted by chesty_a_arthur at 6:34 PM on August 4, 2015 [13 favorites]

this Etsy seller might be a good resource.
posted by chesty_a_arthur at 6:39 PM on August 4, 2015

TIE IT IN A HEADSCARF!! Here's how to tie a bandana. It's the EASIEST thing in the world. You can use anything that's square and about 22x22 inches. If you get a silky type fabric you may need to use a pin or two. I do this to my hair a lot. (It's better than a hat.) Something like this may work. Here's just a solid white or solid green. And a striped one. In fact I'm wearing a gray bandana right now!
posted by Crystalinne at 6:50 PM on August 4, 2015 [1 favorite]

Green fascinator here.
Fascinator with veil but the black might be too dark depending on your coloring and time of day.
Pinky Jewelry is supposed to have fascinators.
Cochina Couture looks promising.
This looks pretty and festive and ships from Redmond.
(Lovely dress. Sympathies on the growing out a hairstyle. I'm with you.)
posted by Beti at 6:56 PM on August 4, 2015 [1 favorite]

Turban? Or a half-turban? but I was really thinking of a headband with some silk flowers/fruit on it and a little veil attached but I can't find an example.
posted by TWinbrook8 at 6:58 PM on August 4, 2015

I think a green flower hair ornament or floral fascinator with green would be just the thing. How about this one? Or this bigger one?
posted by amtho at 7:22 PM on August 4, 2015

Depending on your sensabilities, you might find this banana fascinator really fun, but this hibiscus tiki fascinator is probably a little more appropriate but still fun.
posted by OrangeDisk at 7:37 PM on August 4, 2015

Cocktail hat
https://www.etsy.com/listing/113716099/cocktail-hat-sage-green-sinamey-bow
posted by Ideefixe at 7:39 PM on August 4, 2015 [2 favorites]

No hat; big earrings.
posted by oneirodynia at 7:43 PM on August 4, 2015

You really don't need to spend $100 on a wig, especially if it has bangs to conceal the hairline. Get a cheap black wig with a Bettie Page cut and you'll look fab. Go to a costume store and you can probably find one for like $15.
posted by Ursula Hitler at 8:10 PM on August 4, 2015

Browsing the University of Miami's photograph collection for some pictures of actual Cuban women led me to these ladies. I think a single, large red flower would look lovely.
posted by MsMolly at 8:45 PM on August 4, 2015 [1 favorite]

Response by poster: Thank you for the ideas so far! I am currently liking the idea of a wig, but my husband thinks they are tacky and would rather I make the fascinator thing work. I am not worried about perfect accuracy in terms of what decade to go for, but I definitely want mid-century sleek stylish rather than, say, late 60s Carol Brady.
posted by joan_holloway at 8:50 PM on August 4, 2015

Agree, a big flower would look beautiful in a lovely short 50s-era hairstyle, which could totally be achieved with a growing-out pixie, e.g. a Kim Novak bouffant (curling iron or rollers could take you there), or a gamine-style cut, as seen on Shirley MacLaine, Liz Taylor, or Audrey Hepburn. (Also Ava Gardner)
posted by cotton dress sock at 9:01 PM on August 4, 2015

Not the bandana/scarf, it's what factory workers did on the job to keep their hair away from the machines.

Nthing turban or fascinator.
posted by brujita at 9:12 PM on August 4, 2015 [1 favorite]

Can you show your hair? With face blurred out if you'd rather not be identified? A lot of updated vintage fashions can be a bit overwhelming.
posted by easter queen at 9:56 PM on August 4, 2015

Also, I vote no to scarf as that dress is crying out for something more glamorous IMO.
posted by easter queen at 9:57 PM on August 4, 2015 [1 favorite]

Response by poster: Basically I have Carol Brady hair right now, minus the longer curled-up bits below the neck. It's wispy and greasy and covering my eyes.

For more detail: the bangs are below the brows, and I have HUGE sideburns. I can't do a cute Shirley, Liz, or Audrey. It needs to go back.
posted by joan_holloway at 10:18 PM on August 4, 2015

I forgot about Marilyn, kind of unbelievably - could a hairdresser style you into any of these kinds of styles? Afaik, temporary (non-peroxide) dye could help your hair take a curl, with some heat and lots of hairspray, but a stylist would know better tricks than that. (Sorry for the hair talk, but you've got to do something under the fascinator, right?)
posted by cotton dress sock at 10:51 PM on August 4, 2015

I feel like you should channel Lucy Ricardo going to Cuba and go with something feathery. This place is in Portland and looks very promising.

I think the right search term for you is "cocktail hat" because fascinator will send you to all the upselling wedding stuff.
posted by Mizu at 11:54 PM on August 4, 2015

Seriously, get a Bettie Page wig from the costume store. It's easy, it's cheap and all night long people will tell you how good you look. (Pretty much any woman can rock a Bettie Page 'do.) With that hair and that dress, you'll tear up the joint.
posted by Ursula Hitler at 12:55 AM on August 5, 2015

The dress is fantastic! I think the flower idea is great for that style -- something like this, say.
posted by taz at 2:17 AM on August 5, 2015 [1 favorite]

Turban or flower. The scarf is too casual for the dress/event.
posted by kariebookish at 3:46 AM on August 5, 2015 [2 favorites]

A vintage bandeau hat would be charming. They were popular in the 1950's, especially for cocktail parties. It's kind of like a wide headband made of buckram with wire around the edges, and then covered with velvet or silk and trimmed with all sorts of lxurious materials. You see a lot of flowers, feathers, and birdcage veils. They're comfortable to wear, look great with short or long hair, and are easy to secure with bobby pins. Since they're relatively small, vintage ones can be well withing your price range.

Here's a pretty green one on etsy.
Etsy search for "bandeau hat 1950s."
Cute and inexpensive white one from ebay
Sweet and simple ivory model with a bow, that you could add more colorful trim to if you wished
Not green or technically a bandeau, but I liked the tropical feel
Pretty green feathers, but doesn't come as far down on the sides


Anyway, there's a whole wide world of affordable vintage hats out there to explore!
posted by The Underpants Monster at 8:45 AM on August 5, 2015 [2 favorites]

I think the bandeau is a great idea.
posted by easter queen at 6:30 PM on August 9, 2015