Usehername,
Think future work and places you'll be going not who you would like to be with.
a person's gotta work out 2 things in life:
Where they are going
Who they will take with them.
In that order - failure tends to spell divorce.... actual or relationship rescue...
as somebody old enough to be your mom

I'd suggest
Over the years I've tried to second guess what *someone special* would like and dress that way. Sometimes I'd guess wrong. Even worse when I ask them. Then they tell you and you think "ick" but then try it and waste money! (double ick!)
OK, so think this through (I really wish I had when I was younger...) -
meet man 1 - he likes "a", then you get with man 2 and he likes "b" etc. You end up with a mish-mash of stuff. There's something to be said for being willing to please somebody but only when the relationship is well established. My preferred dress mode is kind of scruffy practical/casual these days (but on the neat end of scruffy spectrum). Now the last man I dated was very particular about his appearance and I tried hard not to attract his look or comments of disapproval if I didn't measure up to his standards. Well silly me for trying. At my age I should have worked out that this spelled Trouble. Yep, after a few weeks he turned out to be a neat/control freak.
Moral of the above stories - dressing to impress may not work and it will cost you ($ or stress/second guessing).
Partly because of the various work roles I've had in life I go for sleek classic items (saves on shopping trips!) that mix/match. Doesn't have to be expensive, just quality materials. If I like something that's "in" I purchase cheap chic (ok, that is ick!). So when needed I can dress up. I even own 3 skirts and 3 dresses. 3 of those were from trying to "dress up" to impress a man. See, you can get older and not wiser....

At work we had image consultants come in for us "techies turned to sales support staff" - and that helped get me a bit more adventurous in style and colour but some of the advice was just icky IMO.
But you know what works is what boosts your confidence and you feel at home in. Nothing is more attractive than somebody who is comfortable in their hearts/minds, skin and clothes!
When I do go shopping

I spend ages staring at what I think I'll purchase, then try it on and really analyse how I feel in it, how it looks and weather it works in with the rest of my gear and all the quality/cost/fashion durability stuff. If it doesn't feel right on me I never get purchase it. Stuff that doesn't feel right when I buy it never feels good when I wear it later. I can never describe what I'm looking for in advance but I know it when I see it. So shopping can be very quick for me if the right stuff is around.
These days I wear just nice pants, tops and sport/travel sandals/shoes. Durable and easy care ... I seldom have to dress up (phew!).
With your figure you can wear anything really - a slim figure can wear anything but keep lines and materials simple to appeal to your INTJness and to keep from having things that go out of fashion and force you to shop again!