“Don Jr. has always wanted to look good in his father’s eyes,” they said.

Not all of Guilfoyle’s fashion missteps can be attributed to her connection to the first family, however.

The new U.S. ambassador to Greece definitely made some questionable choices at times in her pre-Jr. days.

Kimberly Guilfoyle pearls looking serious

We’ve gathered some of the most obvious examples and ranked them from merely unfortunate to totally cringe.

The attorney should have rethought her choice of dress.

As becoming as this ruffled number is, it closely resembles the traditional costume of flamenco dancers.

Kimberly Guilfoyle flamenco style dress 2005 San Francisco Fashion Week

And is that a hint of a peplum we spy?

If so, that also puts the dress amongGuilfoyle’s most outdated outfits.

The fur-collared coat just added more unnecessary shine.

Kimberly Guilfoyle green satin dress and coat with fur collar

This one gets amaisnonfrom us.

Alas, Guilfoyle’s look was marred as well.

Kimberly Guilfoyle temporarily forgot that particular guideline when she attended the 2011 Mercedes-Benz Fashion Week in Manhattan.

Kimberly Guilfoyle Newsom and Dan Abrams 2004

Minimal jewelry and a clutch or handbag was her basic statement.

So we’re not sure what happened here.

The result was a mismatch that looked more junky than funky.

Kimberly Guilfoyle in gray micromini with pink leopard print

In this case, it was a poor match both for men’s designer shoes and dinosaur fossils.

It also unfortunately revealed telltale pale lines rivalingDonald Trump’s worst fake tan fails.

Kimberly Guilfoyle gray dress black scarf black coat with piping

Kimberly Guilfoyle sheer lingerie dress Ermenegildo Zegna store