Reach for a black parka and blue chinos to feel completely confident and look neat and relaxed. Change up this ensemble with a more sophisticated kind of footwear, such as these loafers. While dressing for cold weather can be a bit daunting, outfits like this one make you feel excited. As you reach your 30s, you probably want to start dressing like a grown man. That's when getups like this are a never-failing option.