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Helpful hand: How to give your best guy friend a much needed makeover

Every guy has that one friend who simply isn't up to speed from a fashion sense when it comes to his wardrobe.
Everything from his hairstyle to his footwear scream anything from outdated to downright ugly, but as his friend you have one of two choices. You can look the other way and leave his clothing and style sense to him, figuring that he'll either figure it out or it really isn't any of your business.
The other option: stand up, be honest and tell him his clothing is a hindrance more than helpful and set him on a path to put bad fashion in the rear view mirror. Although this can be a touchy subject, you also have to remember that you're doing this for his own good, and you're trying to revamp his attire for a number of reasons, perhaps so his work outfits aren't holding him back at the office or his personal life isn't all it could be thanks to his pleated khaki pants, sneakers and old man jeans.
So as a close, personal friend, what exactly has gone wrong with your favorite male friend?
Let's start at the bottom: the shoes. Tell him that his tennis shoes or sneakers should be saved for the gym and that he might want to invest in some dress shoes for work and casual slip ons to pair with his favorite pair of jeans.

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And speaking of those denim mom jeans your male friend is currently wearing, find them, take them and burn them as quickly as possible. Now your buddy isn't going to go from zero to 60 just yet so if he's wearing outdated jeans, you might want to avoid getting him skinny jeans or anything too trendy. Let him graduate from his Wrangler jeans and move into a relaxed fit or boot cut jean that fits better and isn't stone washed disaster from the waist down or that ugly blue, bland denim color.
As long as you're changing those jeans, why not adopt a better selection of tops as well as bottoms. That means your tendency to buy shirts too big or too small needs to be replaced with shirts that fit just right and follow a simple game plan: plain color, neat and clean looking, rather than that printed or striped pattern you've been inclined to wear for years.
In the long run, your male friend is going to thank you for telling him what's wrong with his clothing choices, even if the immediate reaction isn't a positive one after you remind him just how bad his fashion choices are.

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