What does your guy like to do for fun? Does he putter about the house playing handyman? Maybe he's into the great outdoors, backpacking, hiking, fishing, etc.? The clothes you buy should work well for his hobbies and how he moves while doing these hobbies. Guys who play ball want clothes they can get dirty without feeling guilty. Guys who enjoy race car events want stuff that's comfortable and that you can easily remove food stains from after an event. Still other guys like clothes that require little "maintenance"; they wash the clothes and wear them and the clothes never need an iron.

Cool clothes are subjective things. Some guys would argue that heavy metal band t-shirts are cool. Others would argue that leather jackets are cool. Edgy is sexy with a twinge of scary but in a good way. There are clothes for that type of guy too. Trendy and hip have their own shopping category as well. Thankfully, you can find all of the above on a handful of websites for men's clothing. As you search, it helps to keep a list of your man's clothing likes, dislikes, sizes, and styles nearby. If you have heard him mention certain things he really likes but does not currently own in his wardrobe, you can look for those items too. Check clothing descriptions for fabric content, especially if and when your man has an allergic reaction to certain fibers and textiles. Then you can find exactly the right item or items to purchase and give him as a gift for the next holiday coming up.