Looking at some of Amy Sherald other works such as:

[I.pinimg.com]

Here is what the MET has to say about 19th Century Folk Art

[quote]They are characterized by sharply defined forms, neatly organized compositions with clearly defined spatial arrangements, some with an almost mathematical precision and symmetry, generalized lighting, equal attention paid to all areas of the canvas, an absence of expressive brushwork, and an overall flatness and linearity. A current, compelling theory about the look of folk portraits is that they matched the face of the neatly and geometrically farmed agrarian landscape. In any case, it is important to recognize that folk artists worked according to criteria set by their rural clientele. As a group, the portraits describe socially reticent sitters eager to record a likeness but shy of declaring personality and emotion. Elements of pride and class status are apparent but circumspect. Portraits record lasting traits and conditions (some are even memorials to the dead), rather than transitory mannerisms and situations.[/quote]

Anyway, Sherald's work reminds me of a sophisticated version of folk art.

I didn't care for either portrait, although Barack looks more like Barack than Michelle looks like Michelle. But even with him ... what is up with him emerging from (or shrinking into) a hedge? Both of the portraits are just "odd" to me, but there's no accounting for taste and I happily leave it to others to have touche-kicking contests about the worthiness of these artistic efforts.

I think the dress is definitely her but I don't see the softness and confidence that is Michelle Obama.

Like @ToakReon and @Crimson67 below, I'd never recognize who the woman was without being told. Her arms are larger than life, she looks tired and bloated, and her face looks splotchy; not at all like the elegant and beautiful woman we've all seen in the media hundreds of times.

Did Donald Trump commission this portrait?

The portrait of Michelle is much more pop art style, while Jacqueline Kennedy's is painted in much more realistic detail. My personal preference is for the realistic detail, but it's more a matter of tastes in art than a reflection on the art.
I don't think it's a perfect depiction, but art is more about emotion than exacting detail.

I agree that it has very little resemblance to her. In My Humble Opinion

I'm not a fan of the Obama's policies and politics, but that is a beautiful portrait. It captures her essence well and is bold in its composition. It has a strangely traditional yet modern quality that exemplifies her status and seems to match her views. The use of color really moves the eye and creates depth. I wouldnt hang it in my house, but it is a nice change from the stoggy and puritanical portrait of yore.

Art is subjective. I've seen the portrait. I don't hate it, nor do I love it.
I don't feel that the resemblance is strong enough, but then, I return to the statement
that art is subjective. I'd rather look at an artist's perspective of Michelle Obama than I would an actual photograph of Melania T.