I typically only go brown shoe/belt with blue pants.
As far as sizing... I just order 2 or 3 sizes and just return the sizes that don't fit. It works very well at places like J.Crew where you can return everything right to the store.
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2014 CC R-Line DSG | 2010 S4 Sold | 2010 BMW 135i Retired | 2006 Lotus Exige Sold