15 Dresses to Pair With Black Heels This Holiday Season

Sponsor Content Created With Who What Wear, Target

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(Image credit: @collagevintage)

When it comes to holiday party dressing, it seems like every year we’re confronted with the same conflict: wanting to wear something new and wow-worthy while simultaneously trying to save what’s left of our cashflow for the many gifts we have to buy. We’re guessing you can relate?

Well, not to brag, but today we’re actually bringing you the ultimate solution—15 killer dresses, all of which are under $40 and look perfect with something we all have in our closets: black heels. Of course, if you’re looking to upgrade those, we’ve also included seven stylish pairs in our roundup, all of which are also under $40, thanks to our very own Who What Wear collection at Target. We know, it sounds too good to be true, but lucky for all of us, it’s not.

So, what are you waiting for? Shop the affordable dresses and shoes that will make your holidays so much better below!

Editor-at-Large

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.