This man has no understanding of color theory or putting together appropriate outfits. As far as dressing like a frumpy middle-aged office worker, he's got the style down. But his individual choices are cringe.
But wearing warm browns/dark oranges with black can be done, but they typically look better with brown bottoms. The sweater doesn't suit that style of skirt either. The outfit would look better with wide legged pants, even black pants. Or without the sweater.
The black blazer with navy dress is a miss too. Black technically goes with everything, but it doesn't look good with navy. You can get away with black shoes, but not a black blazer. White would be a better choice for navy. Navy doesn't always look the same on different pieces due to dye uptake on different fibers and variations on the dye itself, so it's better to use something with more contrast.
Others may disagree with me (but if you do, you're wrong) but pink and red usually look terrible together. A light pink will work with red, but a bright/dark pink competes too much with red visually to make it attractive. The sweater itself doesn’t match the skirt either. Fair Isle sweaters are usually causual, so again pants would be a better choice. A fair Isle cardigan could work with a skirt, but this sweater just screams denim. A large statement necklace will get absolutely lost in the details of the yoke too.
I'm far from a fashion expert, but I feel like most women would know these things. We pick up on these rules during school and church as teenagers, mostly by observing other girls (assuming mom doesn't tell you the rules). Over time you learn that certain things just look right - or don't look right. It's very much a female socialization thing that men will never understand. Men compete with other much differently, women do it with clothes/makeup/hair.
Every women he knows is thinking "oh honey what is you doing honey no" when he walks in a room. But I guarantee they tell him he looks great and that these are his colors/he has great style when he asks for advice. Because that's what we do to people we don't like. People we do like get told "oh honey no" when they ask if something looks good that doesn't. Sometimes if they don't ask!
