So I decided to lean into my tomboy side for casual style too and looked especially for pants on my shopping trip yesterday. I went with a friend who's a long time fan of G-star denim. I always considered this brand too cool for me (or let's stay neutral and say 'urban') but finally made a visit with her. Lo-and-behold: I found the perfect pair of midwaist tapered jeans at half price!
They are very soft and stretchy yet with a substantial feel. My friend claims they really last. The waist height looks timeless to me (though the style probably very nineties) and doesn't dig into my tummy like a higher waist does.

I also got a pair of combat trousers. Have been pinning these like mad lately out of nineties nostalgia and because the sturdy 'worker style' fits my forties tomboy aspirations. A bit outside my comfort zone perhaps, but a steal so worth a shot.

I took some time just now for a quick styling session to show how I might wear these. The jeans look like they'll work as well now as in warmer weather. The combat pants I hope to wear in spring with a black leather jacket when I want to look badass ;). Apologies for all the creasing.

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