For an effortlessly sleek menswear style, choose a grey puffer jacket and navy chinos — these items go nicely together. Complement your look with white and green leather low top sneakers to make a mostly dressed-up ensemble feel suddenly fun and fresh. Be sure this ensemble is ideal for fluctuating fall weather. Those who are curious how to wear modern off-duty outfits as you work your way through your 20s, this combo should answer your question.