One of the most elegant ways to style such a hard-working menswear piece as a charcoal blazer is to wear it with a grey dress shirt. If in doubt as to what to wear in the shoe department, stick to black suede loafers. We recommend this one if you're in search of a winter-appropriate outfit that's as stylish as it is functional. Interested in fashion for guys in their 40s? This combination is definitely worth saving to your inspiration folder.