Go for a pared down but laid-back and cool choice pairing a bomber jacket and a pink sweatshirt. To infuse a more laid-back vibe into your outfit, make dark green canvas low top sneakers your footwear choice. If you feel uninspired by your transitional weather fashion options, this outfit just might be the inspiration you need. Those wondering how to pull off cool off-duty outfits as you go through your 20s, you have your answer.