First, take a girl that is the kind of girl you want to game with you. She does not have to be a girl you plan on dating. It can be your brother’s wife. Just explain you want a woman’s opinion. That woman is going to dress you in the way that looks good to her. It will attract other girls just like her.
I usually buy her lunch, or if she sees something to wear that she thinks is cute, I buy that for her, if I have the cash.
Second, although custom tailored suits do look good, you can save a lot of money by buying off the rack and having it touched up by a tailor. Custom tailored=$1500 or more. Tailored off the rack=$300 to $500 for the suit + $100 for the tailoring.
Third, do not worry about this year’s fashion. Last year’s looks very good for many years and usually is about half the price.
Fourth, do not skimp on material quality. Better quality usually means it will last a lot longer. Cheaper material might look the same when bought, but will get thread bare much sooner.
Finally, if you are going to accessorize, buy quality. That $5 tie pin will make a $1500 suit look like $5. A $10 polyester tie will never fold right, but a $50 silk tie always looks sharp, even you don’t bother to tie it.
Oh, one last thing. Take special care of these. A crumpled tie, or a suit you left crumpled on the floor for a few days is going to be the attention grabber when someone sees you. And, it won’t be good attention. Also, get suits and ties dry cleaned by a high quality cleaner. $1.75 is ok for shirts, but not for expensive stuff. The cheap dry cleaners clean many items together. High quality cleaners clean single items at a time. Cheap cleaners will clean stuff, but high quality cleaners remove things like lint.