Marrying a black wool blazer and navy vertical striped dress pants is a guaranteed way to infuse your day-to-day arsenal with some masculine sophistication. A pair of black leather tassel loafers is a great option to complete your outfit. When it comes to dressing for weird transition weather, nothing beats a knockout outfit that transitions easily between seasons. So if you need outfit ideas on how to dress as you pass the big three-oh, this ensemble is ideal.