longbough

I just get what feels and looks good on myself.

I won't characterize my stuff in any particular way but I have a decent variety. If I buy more expensive stuff it's only because I "know" what I'm paying for ... not because I'm a "label whore" ... quite the opposite. There's crappy (poor quality) brand-name stuff as well as great off-brand stuff. It helps to know your materials and construction ... and to know what goes into the construction of, say, a good suit, for example.

There are Armani suits and jackets that look great on the rack but look ... overstated (for lack of a better term) when worn IMO.

On the other hand, the best suit I ever owned was made for me by a friend of a friend ... this little old tailor in the back streets of Lima, Peru - who built me a complete suit for the cost of materials plus $150 for his labor. I would have purchased 3 or 4 up front if I hadn't been so arrogantly skeptical from the start. Boy was I wrong. 2 fittings later I had a suit that felt like no other ...

When I lived in the UK I purchased an unconstructed David Moss herringbone jacket for only 50 pounds (it was on sale - being discontinued). I swear it was only 2 weeks later the exact same jacket appeared as a new Hugo Boss item for 150 pounds! It was the EXACT same item with a swapped label (both made in Malaysia, too, as I recall).

Moral: Know what you're paying for ...

At the moment I'm wearing a John Varvatos print shirt, a pair of bootcut 7's jeans, Prada leather belt and black Bruno Magli Manado loafers (no socks).
But tomorrow I'll probably be wearing a simple Gap black T-shirt under a comfy Woolrich forest tremont shirt and Citizens of Humanity Evans jeans ... albiet with brown Prada loafers (the Pradas are overpriced for the construction IMO ... but they look and feel really nice).

If price is no object go to Saks Fifth Avenue and try trousers from Dolce & Gabbana and Ermenegildo Zegna. Actually it seems I own more Zegna than any other name - I just like their stuff ... shirts, and trousers. For shirts also try Hugo Boss, Richard James and Prada.

I don't know what your budget is ... but at the very least you should try these items to get an idea of the look you'd want. Then shop around for the "look" rather than the brand name. You can get shirts from Express Design Studio, for example, that have the same cut as the Hugo Boss shirts. I have a couple of their shirts which look great at a fraction of the cost. They look about 90% as good on me as my Hugo Boss and Richard James shirts. The more expensive stuff certainly feels better because of the fabric.

If your sole object is to look good ... don't skimp on the shoes. A great pair of shoes will make an otherwise nondescript outfit elegant ... conversely, a terrific outfit will be destroyed if your shoes are lousy. John Lobb, Bruno Magli, Loake, Prada ... all have nice shoes. And don't rule out Ralph Lauren shoes, some of which are actually from Edward Green (excellent English shoes).