Having a mega clear out - but facing some tough decisions!

[Notcontent]

So - following another thread, about having some sort of mid 40s crisis and hating how I look, I decided to finally have a mega clear out of my clothes and try to keep the stuff I actually wear - not stuff that’s actually rather nice, but is just not me anymore/makes me feel frumpy.

However - where do you draw the line? E.g. about 7/8 years ago, as a major treat, I bought a pair of the Acne ankle boots that were all the rage and copied by everyone. They are still in excellent condition but I just never reach for them (as tend to wear flats on a daily basis) and fear they probably now look dated. Or not? I also have various heels that I have not worn in about five years... Should I keep them?

You need an honest friend to help!

I tend to use my sister because if I look crap in something she tells me.

I'm not familiar with the boots, but could you get them out and keep them somewhere accessible, and if you don't wear them within 6 months then sell them / donate them?
They're no better in your cupboard unworn than being given away.

Doesn’t sound like they fill you with joy, so Kondo would say sling them.

Yes, I do need an honest friend but sadly don’t have anyone I could really ask!!

If they are the Pistols I've kept mine they are a basic ankle boot. I still wear them occasionally.

Why don’t you have a look on Pinterest for some of the outfits you can create, using your existing clothes, with your boots first. Basically, try to find a way to make them more current, if possible - hard to say without having seen them

You could post a picture of the boots on here for honest-yet-tactful (mostly) views from S&B-ers?