I know. I do the same.
Download the ‘Stylebook’ app (there are other apps but I’m using Stylebook). I’ve had it for years and years but always got overwhelmed. Don’t get overwhelmed. Start small.
Start uploading content based on this cruise rather than everything in your wardrobe. (I’ll tell you at the end my method of uploading and be on hand for support if you decide to try this).
Upload your sandals first because you’ve chosen those for very good reasons. Plus one pair of smartish shoes. (Google the 5,4,3,2,1 method which suggests a third pair of shoes, but I stuck with 2).
Then upload four ‘bottoms’ in your cupboard that you wear and like. I went and bought jeans off Halara because of social media advertising and have to say they are fab. Make one bottom smartish - like black trousers/skirt.
Next, pick out five tops in your wardrobe. Look through everything - you might find stuff you haven’t worn for ages. I did.
Once you have these items all in the app, mix and match the items using the ‘looks’ feature. Consider swapping out anything that is standalone (only appears in one look if doesn’t go with anything else) - either introduce something else from your wardrobe to take its place or now shop specifically for an item you KNOW needs to go with items you’ve already got. So, you see, your shopping is no longer aimless.
The looks feature really helps to pick out combinations, quite quickly too. You’ll find, for example, your ‘smart top’ can be made more casual with jeans (or similar), but look super smart with black trousers and accessories. It’s faster than trying everything on.
At this stage I started to focus on accessories because they are small and you can take a bunch of small things to make an outfit look different. It was ridiculous how many people told me I looked nice just because I tied a scarf around my neck 🙄. I ended up trying to upload most of my jewellery and shawls and scarves to the app to mix things up in the looks as well.
I also went and bought a jacket, but I was shopping with purpose now instead of my usual panicked scatter-gun shopping. I also have lots to return that I can see won’t get worn much because they don’t integrate with my favourites.
Once you’ve got a bunch of looks created you can create a packing list from them. My final packing list had 25 items on it, which made up 13 looks (I was away for 3 nights!) Of those items, 13 were clothes, the rest shoes and accessories. I’ve attached examples of looks from my list.
What I still can’t help with is ‘style’ and ‘critical judgement’ - and I still have strong opinions on judgy-fashion and how horribly it affects women. (See for example some of the comments in response to sandals you had narrowed down as a choice). So I’m sure someone will come along to my looks and say ‘I wouldn’t have put that top with those jeans’ or something similar.
So I haven’t cracked ‘style’. But I did think I looked like I had “made an effort” - which is another horrible category we get judged on.
On the shopping: if you see something you think might be nice you can download and add it to the app to preemptively test it with clothes you’ve already got there.
—- My Stylebook method. I take a photo of the item in good light usually on my laminate floor. I then take it into the adobe express app and one click remove the background there ( don’t start the free trial). Stylebook can remove the background but not as cleanly as adobe express. That’s the image I upload.
I’ll keep checking on this thread if there’s anything else I can help wrt process or using the app IF you think you might like to try this approach. I really hope this helps. I know how horribly stressful it is.