Vanessa Trump strikes us as the pop in of woman who’s most comfortable in jeans and a T-shirt.
In the now-viral post, she’s wearing a white tank and dark denim.
But sometimes this uniform hasn’t served her well.

And then there are fancier occasions when her looks have seriously missed the mark as well.
It draped beautifully off the shoulder and flaunted her toned back.
This look missed the mark, however, thanks to its material.

Natural fabrics, such as silk and linen, are the worst culprits for wrinkling.
Short of getting her dress steamed in the bathroom, Trump had no hope of recovering from this creasing.
A lighter bag, in a metallic or neutral shade, would have complemented the look better.

When she began dating Donald Trump Jr., she continued to mingle with N.Y.C.
But even this exposure to upper echelon living didn’t mean she always dressed appropriately.
Other guests were more dressed up, including Trump Jr., who donned a suit.

Other women were in dresses and heels.
It just missed the mark because it wasn’t appropriate for the occasion.
This wasn’t even a stylish enough outfit to be sitting in the last row.

It looked more appropriate for the nosebleeds at a Britney Spears concert.
Add in boots worn over the skinny jeans, and it all screams 2006.
And why the deep black boots?

They don’t look right with the rest of the look, throwing it out of balance.
A year later, she hit the red carpet while attending the annual Operation Smile gala in N.Y.C.
Unfortunately, everything about her look for the event felt off and somewhat Trump-ified.
Like in this instance.
There’s also something about her posture that makes Trump look like she’s uncomfortable.
So the parents didn’t have any newborns or kids on the way and hit the town.
This time it was for another Operation Smile event, held in Beverly Hills, CA.
And it was a gala.
That’s right, a gala.
Where you get dressed up in formalwear.
Not an oversized, unflattering tunic and black pants.