To pull together a relaxed look with a twist, you can dress in a grey hoodie and a white and black plaid flannel long sleeve shirt. If you're hesitant about how to round off, a pair of grey leather low top sneakers is a good pick. It's a viable option when it comes to picking out a standout look for unpredictable fall weather. Those who are curious how to dress fashionably as you drift through your 20s, you have your answer.