Dress in a grey crew-neck t-shirt and grey ripped jeans, if you prefer to dress for comfort without looking like a slob to look stylish. A trendy pair of black suede chelsea boots is an easy way to power up your look. When leaves are falling down and fall is in full swing, you'll love this combo as your uniform for unpredictable fall weather. Those who are curious how to stay stylish as you mature into your 30s, you have your answer.