I see only two options to this one:
- Wear your favorite jeans and don’t try too hard with anything new
- Go to a shop and try as many models as you can, until you’re happy.
- A first date is anyway an occasion when you want to impress/appear at your best, but without giving too much pressure or emphasis to what’s happening (at least if you want to make your potential partner feel relaxed about things);
- Fashion should be, as you are sensing, at your service (and not the other way round). So any item you’re going to wear should be in good proportion with your body and features. And there is no other way to achieve this, than trying things on – I cannot help that much without seeing you and what you are considering.
Here some general rules to choose denim:
- Length should be in proportion with your size. Loose fabric reaching the top of your shoes shouldn’t be bulky or super tight either.
- Rise (the crotch!) follows the same principle: good proportion, no baggy or extremely tight fabric.
- Width should gently follow your leg shape. Again: no bulkiness, no super sexy stretched denim.
- Pocket: go simple with a classic stitched pocket that shows your butt
- Wash: unless you have a passion for distressed or ripped denim, I would again go for a classic choice, so the eye can notice the body, not the frills.
Enjoy your date!