For a classic and casual menswear style, wear a charcoal plaid wool blazer and grey chinos — these two items play beautifully together. White leather low top sneakers will immediately tone down an all-too-polished ensemble. Seeing as the weather is getting chillier with each day, this outfit appears a good choice for the transitional season. As you're moving from your 20s to your 30s, you want to start dressing more maturely. In this case, looks like this are perfect as inspo.