I also appreciate that this isn't he 'help elisiX thread'.
I'm clearly not entirely sure what I want and I've gone about things the wrong way perhaps with my purchases, but I can live with that. Nothing I've bought is 'rubbish'. However I recognise that I need to learn how to pull certain things together to achieve the desired result. There's 3 or 4 scenarios I have in mind and I see them as requiring me to dress differently for each. I may be wrong, but here goes.
Firstly some context. I work in a casual office where most people dress terribly. Think software developers in Metallica t's and ponytails. So there's certainly a reason for not overdoing it unnecessarily in my office. When I have important meetings or clients visiting, I like to dress up to look more professional but it's certainly not required of me. It's just something I like to do.
1. Work Casual - This is essentially the 'workwear' look which you see from me most of the time. Slightly preppy, but essentially jeans, chinos, oxford shirt, plaid, etc. This is in many ways how I always have dressed but I've tried to pay closer attention to fit. Sleeves, shirt length, cuffs and so forth.
2. Work Formal - I use the term formal loosely, but I'm talking about throwing on a blazer, button down tucked-in shirt and not wearing sneakers - though essentially the same clothing as above.
As above per 1., with some old, very average no name blazers which I've owned for years.
My intention is to buy a couple appropriate blazers for this purpose.
3. Weekend/Work Casual 2 - This is me trying to embrace some of the more relaxed fits I see on here with more luxurious materials and brands. These fits have also crept into 1.'s territory for days when I am positive I wont be seeing clients.
4. Evenings - I see this as being essentially 3. with a blazer for dinner with friends etc.
In terms of boots/shoes from my original question for Friday evenings (for 4. above), I think these MMM side zips fit the bill. Although as suggested, a Chelsea boot would do the same thing. Again, thinking slim black denim (or trousers), and a t or shirt with a casual blazer like the Barena I linked earlier from TBS.
Edited by elisiX - 8/10/13 at 8:30am