2) Yes, you're good looking and when it comes to style already doing a lot of things right (actually you're doing much better than most guys I've seen).
1) Let's do this picture by picture (a quick critique),
1st picture: the details are a bit vague due to low quality of photo, shoulders on the jacket are a bit too wide but all in all, the fit is not so bad - for pick up, I'd take slightly too tight over too loose any day
Nice touch with the pocket square.
One thing I'd change is open a few buttons on the shirt. With this outfit the line between cool-sexy and tryhard-"look at me" is very slim and I'd prefer to see you channel your inner Johhny Depp and make the outfit a bit more laidback with a few shirts buttons open.
2nd picture: the hair is all over the place but overwise looking solid. One thing too consider: maybe a pocketsquare to add some color (something with a red flower maybe?). Full dark-on-dark outfits can work well if you feel like going full on James Bond mysterious persona, but overall they lack a touch of fun, excitiment.
3rd picture: Is this the same outfit? Can't really tell due to different qualities and angles in pictures.
4-7th picture: Now WTF has happened here?! That v-neck needs to burn, seriously
a) there's never a good reason to wear a v-neck with a pocket. b) the cut is way too loose. c) it looks like you're tucking it in, which agains is a big NO.
Gold accessories also look quite out of place. If you'd like to follow Mr. Depp and wear a lot of accessories that's great, but keep in mind that they all need to be from the same/similar "theme".
8?th (the one in leather jacket): looking great!
9th: Spot on!
All in all: your classier outfits are well executed, but the "trashy" laidback aspects need some improvement. Hair is very much hit or miss - sometimes they look quite good, in other pictures it looks like a bird's nest
One more thing I'd consider - suits and classy outfits tend to look good on a man, but they are not always the optimal approach for pick up (very easy to fall into the image of provider) - you might want to try out a bit more rugged-sexy look if it suits your personality.
Anyway, just few quick thoughts, hope it helps. Let me know if you have any further questions.