Cheers guys - seems like we have a decent cross-section of tastes
I feel very much in a no-mans-land regarding clothes currently. I've never made much of an effort with how I dress and tend to be function-led; one of the reasons I love the combats is they'll hold loads of practical gear and are pretty versatile (the only time I don't wear them is for formal stuff; even for dirty work I wear old worn / knackered examples). At the last count I had 20 pairs having stocked up after my particular favourites were discontinued
I've recently bought a couple of really nice (Mountain Equipment) technical fleeces which currently get worn daily by default as I absolutely love them; however I have to be careful as to what I'm doing since they were bloody expensive. Now I know I like the sizing, cut and quality of the brand (tried on everything else in the shop and these were by far the nicest) I'll keep an eye out for used / discounted stuff from them.
I want to dress smarter and objectively can see how a jacket and shirt or whatever makes me look "better" although at the same time I feel somewhat uncomfortable since it doesn't really feel like "me". I pushed the boat out recently and went out in a blue pinstripe suit jacket, light blue shirt and chinos; which felt good at the time but looking back at the photos made me look a bit like an estate agent.. still love the jacket though so will look to dial things back a bit with a more casual white linen shirt and some black jeans.
To an extent it's the same with the suits; it does wonders for my non-existant self-confidence to look in the mirror and like what I see; however realistically I'm unlikely to get many legit opportunities to wear one.
I spent a good chunk of yesterday OCD'ing my suits in an effort to better understand what fits me. I measured the pertinent dims of all and made some notes on how they fit me (along with my current measurements and weight). This has helped me decide what to keep (sadly it looks like the recently-acquired blue Italian pinstripe effort will be going as the fit's not great) as well as reinforce that what else I have fits me reasonably well and allow me to shop for stuff online with more confidence.
Having (to an extent) just cleared out my wardrobe I'm now going through my chest of drawers in an effort to get a better idea of what I have, and what can go to the charity shop. Problem is I can usually think of a reason to save everything
Sorry for the doubtless boring ramble; I appreciate the ability to do so though as it helps square things in my head..