How-To: Make A Retro Dress Modern

Q. Hi Jordan!

I’m a bridesmaid at my friend’s wedding in November, and will be making my dress out  of a dark eggplant chiffon and using a vintage pattern

I’m not sure what shoes to wear with a long, flowing dress like this in the winter. Are strappy shoes too summery? I don’t want something matronly, and closed-toe shoes under a long funky dress can feel kind of stuffy if they aren’t sky-high.


A. First, I love how original you’re being with this dress - I especially like the longer version on the left, and think that if you change up the sleeve a little (maybe going for a 3/4-length sleeve or making the dress sleeveless), it’ll maintain that great retro vibe while still looking modern.

See? It’s actually not all that dissimilar from this gorgeous Haute Hippie dress.

Just for fun, here are a few more ruffly ’80s-throwback dresses (L to R: Dolce & Gabbana, Miu Miu, Roland Mouret, Dolce & Gabbana).

For shoes, you definitely want to play against the vibe of the dress a little, and you’re right: close-toe shoes with a heel low enough to dance in all night run the risk of looking a little…mumsy. (Do people still say “mumsy”? Did they ever?)

So my suggestion would be either cage heels (although strappy shoes are fine for weddings year ‘round, a cage style is a bit more unexpected and fun) or a peep-toe pump with some interesting details. In terms of color, eggplant can work with everything from black to metallic to snakeskin to nude - although if you go for an unexpected shade you may want to check with the bride first, to make sure that she doesn’t mind and that it won’t clash with the bouquet. (Above, clockwise from top left: Prada, Nicholas Kirkwood, Alexander McQueen, Roberto Cavalli.)

Finally, for your accessories I’d go modern and streamlined: an envelope clutch that matches your shoes, simple earrings, and maybe a bangle on one wrist.

Bridesmaid Style: Simple Black Dress

Q. Hi Jordan, I have chosen this dress from ASOS to be a bridesmaid in my friend’s wedding, but am torn between keeping it at its current length or hemming it so that it hits me right above the knees. Could you offer any styling suggestions?


A. I love that dress, and actually think there’s no hemming necessary: it’s very elegant in that midi length. In keeping with the slightly retro, Audrey Hepburn-ish feel, I’d say go for a simple slingback pump in gold (‘cause it’s a party!) and add a couple of slim bangles…and then go the Angelina Jolie route and add some emerald earrings for pop (and to give a nod to Spring).

P.S. For those of you who are as into this dress as I am, just an FYI: it’s $90 (!), and also comes in hot pink. Love love love.

Product info after the jump.

J. Crew bangles, Stella & Dot earrings (or try these if you want something a little fancier), Kate Spade slingbacks.