You'll be surprised at how super easy it is for any man to get dressed this way. Just a grey hoodie teamed with a dress shirt. Get a little creative when it comes to footwear and add a pair of white and navy athletic shoes to the mix. This ensemble is a bright example you can still be fashionable while bundled up. As you slip into your 30s, you want to start dressing more maturely. If that's the case, outfits like this are a never-failing option.