NYC style blogger wearing Shoshanna windowpane dark charcoal dress with tights and tall black boots
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Meet The Parents

Meeting your significant other’s parents for the first time is the best!  If, by best, we mean terrifying, stressful, and potentially awkward.  At the very least, you can style yourself for success in an outfit that makes a wonderful first impression.  

Shop The Look ×

SHOSHANNA

Upton Dress (similar HERE and HERE)

SAM EDELMAN

Hai Tall Boots (similar HERE and HERE)

THEORY

Small Drawstring Bag

WOLFORD

Velvet De Luxe Tights

The Vibe:
Styling Tips:
NYC style blogger wearing Shoshanna windowpane dark charcoal dress with tights and tall black boots and theory bag
NYC style blogger wearing Shoshanna windowpane dark charcoal dress with black theory bucket bag
NYC style blogger wearing Shoshanna windowpane dark charcoal dress with tights and tall black boots and black bucket bag

There’s a lot riding on this meeting, and it can be tougher than any job interview you’ve ever had.  You want to put your best foot forward while simultaneously not coming across like you’re trying too hard.  Essentially, you want them to like you more than they like their actual child.

SO, opt for a dress that showcases your I’ve-got-my-act-together spirit along with effortless elegance that lets them know you’ll never be late for plans or forget to write thank you notes. The Upton Dress by Shoshanna should do very nicely.

 

SHOSHANNA

Upton Dress (similar HERE and HERE)


SAM EDELMAN

Hai Tall Boots (similar HERE and HERE)

In a classic black and white windowpane with special details at the shoulders and waist, this look has a soft polish about it.  A shorter hem calls for a little hosiery and a high boot, because if you don’t dress for the weather they’ll think you’re a lunatic.  A small bucket bag contrasts the checked pattern in the dress and also suggests that you enjoy geometry (and we don’t hate sending subliminal messages about your high IQ).  A high neckline gives off the impression that you will never embarrass the family. Keep accessories simple and delicate, allowing any maternal compliments on them to give you holiday gift ideas—be resourceful!


NYC style blogger Mary Orton wearing Shoshanna windowpane dark charcoal dress
NYC style blogger wearing Shoshanna windowpane dark charcoal dress with tights and tall black boots on city sidewalk

The right dress can take at least a little pressure off a potentially intense meeting with people you may be spending major holidays with for the foreseeable future.  When styled well, your dress can give you the confidence to deliver charming banter like a pro and exude an overall aura of awesome aimed in the parents’ general direction.  In sum, you’ve got this.

 

SHOSHANNA

Upton Dress (similar HERE and HERE)


SAM EDELMAN

Hai Tall Boots (similar HERE and HERE)

Check out more of my favorite dresses perfect for meeting the parents below!

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