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Your desired look would be completely incongruous with the life of a Greenwich plastic surgeon, so I have no choice but to wholeheartedly recommend against any further pursuit of the Dior Homme image. If you'd like to stand out amongst your surgical cohorts in an edgy fashion, might I suggest getting a "skull and bones" window decal for your Bentley?
You really don't look bad. Much, much better then the first pic. Grow your hair out or something if you wanna be cool. Jacket looks slightly long though but still seems to fit pretty well.
That jacket looks fine. It looks like it fits, although I am not crazy about the collar. Skinnier jeans might work better. I don't care for the boots but that is just me. This doesn't look like a catastrophic failure. Why are you saying you can't pull it off? It sounds like you are not comfortable taking this leap right now. If that is the case, you shouldn't rush into it.
Skinny black coated jeans, military inspired beat up black boots, slim but drapey loose crew neck white shirt or RO style tank/tshirt, and you can even keep the leather jacket. Good to go
Check out Lova and BBlessings recent lookbooks. I think it's a good compromise between classic preppy and interesting modern. Also, do yourself a favor and find a place where you can find some good skinny jeans to try on. See how it feels. I think you'll be surprised.
Your desired look would be completely incongruous with the life of a Greenwich plastic surgeon, so I have no choice but to wholeheartedly recommend against any further pursuit of the Dior Homme image. If you'd like to stand out amongst your surgical cohorts in an edgy fashion, might I suggest getting a "skull and bones" window decal for your Bentley?
This is a the first time I took a WAYNT photo and I definitely look different than what I've seen in the mirrow.
Also, if raw jeans fall in a closet and no one is around to hear it, does it make a sound?
Nothing wrong with dressing a certain way if that's what your life is like. You're going to be a doctor, not an artist. There's no need for you to be edgy, and in fact it seems a little inappropriate.