They both would make you look like you are trying too hard to keep up with the trends. Sexy perhaps but you're gonna wear them like for 3 weeks before everyone has already seen ENOUGH of them lol!!!

I tend to prefer more expensive MATERIALS for clothes, not the LABEL that's all trendy. Like, take a skirt like that, but instead of worn out denim, maybe like a tweed and worn with 80s leggins and a pair of stilettos. Hint! Spend the $$$ on your SHOES, jewelry, and handbag!!!
The jeans are cut too low (I'm ignoring the HORRIBLE wash, and all the holes) again giving the try-too-hard look. Jeans are funny... they might look great in the catalog but it's an item of clothing you REALLY need to just spend several hours shopping for and trying out the different cuts in person. It is pretty tough to nail it the first time out of a catalog, unless it's a classic from like JCrew or GAP that you have experience with how they cut their clothes.