Pair a windbreaker with skinny jeans if you seek to look casual and cool without trying too hard. If you're puzzled as to how to round off, enter a pair of white high top sneakers into the equation. Keep this combination in your head come warmer weather, and we promise you'll save a lot of time getting dressed on more than one occasion. Wondering how to nail casual dressing as you slip into your 50s? This pairing is a practical example.