I hear you! Went through a similar process recently before a holiday to Tenerife. We went to a really nice hotel, so I wanted to look put together.
I played it fairly safe and stuck to classics too. Dressed for my body shape and in colours that suit me.
A few outfits I wore… Tailored black trousers from The Frankie Shop with a black waistcoat from Next, finished with chunky black sandals and a simple envelope leather clutch bag. I felt so chic.
An oversized linen blue and white shirt from Arket with tailored navy shorts, tan belt, and tan sandals and a nice basket bag from Sezanne.
Cropped linen trousers with a simple white tee, tan sandals… etc.
But this was just my holiday stuff. At home, I’ve opted for wide leg jeans and trainers, with basic tees and jumpers from Cos and Uniqlo. I love a cardigan too, worn as a top. In winter, oversized coats. I have one from Norse Projects that goes with everything.
My trainers are New Balance 990s. In classic shades. They’re super comfy. I’m avoiding adidas because everyone is wearing them.
For smart stuff, I have pointed flats or loafers. Pointed ankle boots. Slouchy trousers. Nice blouses or shirts. All in simple cuts. Nothing loud.
I love Parisian simplicity but I also love a little edge/street style.
My point is? Enjoy the process of seeing what you love. Be creative. Figure out your proportions and suitable colours. It makes the world of difference.
As for trends? I’d love a barn jacket or boxy oversized denim jacket. Alas, I look absurd in them. So I’m trying to figure out something current for spring summer. A cropped bomber jacket or cardigan with wide leg jeans or trousers seems to be the answer.
As for my trusty Gap denim jacket from two decades ago? I gave it my mum.