Wear a grey plaid wool blazer with charcoal dress pants - this look is guaranteed to make an entrance. For something more on the off-duty side to finish off this look, complete your outfit with a pair of dark brown leather desert boots. When it comes to dressing for fall, nothing beats a neat ensemble that will keep you snug and looking your best. In your thirties, you probably want to start dressing more maturely. That's when looks like this become very relevant.