Try teaming a trenchcoat with a long sleeve shirt to exude manly elegance and polish. For something more on the daring side to complement your look, add charcoal athletic shoes to your look. As you can see, this look is a really savvy pick, especially for weird fall weather, when the temps are dropping. Think it's hard for middle-aged men to nail edgy off-duty outfits? This combination is a powerful demonstration of otherwise.