80s era garments often present a unique styling challenge; they're often a wild print, an exaggerated fit, or in the case of this houndstooth double-breasted day dress, they have a strong "office power suit" look that at first glance, doesn't seem to translate well into how we might dress today.
Personally, I like to tackle the challenge of styling a strong 80s "workwear" piece by roughing it up a bit. It seems counterintuitive to do this; pieces that are inherently strong silhouettes are pieces we are always told to "soften" with more feminine touches. However, with this particular dress, it just doesn't work. To my mind, the houndstooth print is really the main character here, and I didn't want to convolute that with a bunch of fussy romantic accessories and shoes.
I went with equally strong accessory pieces and shoes that lend more of a boho Western-meets-street vibe to this dress, neutralizing its 80s secretary feel and giving it a more universal, go anywhere appeal. And an added bonus? Blousy 80s dresses are comfy! And.....the holy grail of dress attributes, this one also has pockets!
But I digress - really, the most important accessory to consider pairing with a dress like this is your shoes. These open toe slouchy Donald J. Pliner booties (Y2K era - bought secondhand in the mid 2000s) provide just the right amount of toughness without being overly studded or embellished. In fact, I'd go as far as to say that swapping-out an expected pump or heel with a vintage dress really is the key to bringing the look into the current decade. In this case, it's a nod to the era, but not walking around looking like an extra from Working Girl with Melanie Griffith. Am I showing my age? Meh, whatever.
So give it a try. The next time you're vintage shopping or thrifting and see an 80s dress that speaks to you but can't see how the strong shoulder and/or oversized styling is going to translate, grab something unexpected to pair with it. It will probably surprise you!