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Male Makeover: Telling your favorite male friend he's outdated doesn't have to be difficult

Whether they're in the midst of a mid life crisis or on the cusp of 29 and still dressing like a college student, men sometimes forget what decade it is and just how they should be dressing.
It's not always so much about age but whether or not your ensemble comes across as fashionable or forgettable.
Such is the stylish roller coaster that is how men dress, and whether or not it's appropriate for you, as their friend, to spout out the one word that will make them cringe: makeover.
Telling a close male friend that their look is outdated or flat out repulsive isn't an easy chore, and should be reserved as a task that is done seamlessly, rather than coming out with guns blazing and making them feel too bad about their wardrobe too quickly.
You may want to suggest a shopping trip as a birthday gift and then begin to nudge them in the direction of jeans from this era or perhaps a nice collared, button up shirt that is fits them well. Far too often, the attire isn't made a priority and just any, old T shirt, pants or complete outfit will suffice.

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This is especially frustrating when you have a friend that is in his 20s or 30s and by all accounts shouldn't be dressing like he's 50 or 60. If you invite him to a casual party, and he shows up from head to toe looking like he's there to do your taxes, then it's time to get him to a retail store immediately.
You're talking about hitting the town in pleated, khaki pants and a tie that looks like it was handed down to him from his grandfather, when a nice pair of jeans or a laid back collared shirt feels more appropriate.
That same mid 20s or 30 something soul also needs to steer clear of dressing like he's fresh out of a dorm room. Rocking that backward cap or adopting a teenage fashion sense at 35 years old cries out to your friends to pull you aside and attempt to makeover what is left of your stylish self respect.
If luring him with the promises of a shopping spree won't cut it, maybe it's time to be direct, and just flat out say it. Just be crass but respectful and tell him that his clothing isn't cutting it.
If that's too harsh, try the complete opposite: Shower him with compliments and tell him how much you love him or maybe point out a few outfits the next time you're at the mall, and say "you'd look good in that."
This shows that you're not barking out orders but rather taking an interest in his attire, and simply want him to look his best. If he feels empowered, he may lose the little boy or old man clothes for good.

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