Ever want to take a friend under your wing?

[nicholascrawford]

I have a few friends going through extended adolescence as they approach their thirties, just having a hard time getting traction in life. Then, I've got a few friends who are progressing along but just not dressing to reflect their newfound success.


Has anyone gotten a friend to go along with a wardrobe refresh at your prompting? Did they approach you looking for a What Not To Wear mentorship?

[alan]

I've got one friend that kind of sits at the opposite end of the spectrum. He dresses like his dad (and not in a classy way). Everyone calls him the old man. He's a super nice guy, and I don't want to offend him with any suggestions so I just keep my mouth shut.

[trash]

I'd offer some basic advice is they asked, but I wouldn't do so unprompted. It can be hard to see a good friend wearing square toed monstrosities because they don't know any better, but have to have to cautious of coming off as condescending. If they see you dressed well and want to know how to do it, that's great, but if they don't ask, let them be. And if they did ask, I'd go easy on the enthusiasm so as not to come off as a total clothing freak

[alan]

If they guy is similar to your size and you're getting rid of stuff, you could say "I'm just going to Goodwill this stuff if nobody takes it. Do you want any of it? I love it, but it doesn't fit me anymore."

[LesserBlackDog]

I try not to offer unsolicited advice. If guys I know like the way I dress, it's probably easier for them to learn from observation than for me to try to proselytize to them.


Generally, when people ask me for style advice, it's folks looking for me to regurgitate the "rules" of dressing professionally, i.e., "How long should my tie be?" "What color shoes should I wear with this suit?" and so on.

[jason_carreira]

My GF tried to get me to dress better for a while, but it didn't really stick until it was something I wanted to do. I think girls grow up looking at and learning this stuff, but as guys if we're as clueless as I was we have a LOT of catching up to do, and won't do it unless we're really self-motivated.

[alan]

Nobody in my everyday life asks me for style advice. My co-workers openly prefer their Dr. Martens and faded denim over what they see me wearing. And most of my friends already dress well, even if they rarely dress up.

[Big_Scooter]

I've taken one friend shopping a couple times. Just for some basics. He started getting compliments as soon as he wore his new gear, so I'd be surprised if he doesn't start doing better on his own. None of my close male friends dress particularly well, though I have a few female friends who dress absolutely adorably. Many girlfriends of my friends try to hint that I need to take their boyfriends shopping

[Big_Scooter]

Actually, my best friend in the world usually wears camo colored sweat pants and either a hoodie or a t-shirt, depending on the season.

[hornsup84]

Unprompted advice will generally make you sound pretentious. If you feel the need, throw in a joke here and there about certain items, but I wouldn't push it or they'll just push back and be offended.

[bruschetta]

Yes. I've taken all of you under my wing, in a sense, by exposing you to my innate sense of class and charm. You're welcome.

[jason_carreira]

"Unprompted advice will generally make you sound pretentious."


apropos of nothing, I'm sure

[Glock13]

I have done wardrobe makeovers with three of my friends. It is funny how they are hesitant at first. They all say the same things when you make them try on things outside of their comfort zone. I have found getting them into decent shoes is the hardest. Another tip I have found is to bring a female or even better, find a female associate at the store to help. All three have had the same response afterwards though...they feel like new men. I helped one of my friends while we were TDY to Las Vegas a couple of weeks ago. He was a little hesitant (especially with the suede boots). After he got a few looks from girls in Las Vegas though, he wouldn't take them off. He spent a good part of the rest of the weekend texting girls on his phone pictures of himself.


The one thing I have found difficult though is that many guys think after they go shopping once, they are set for the rest of their lives. I had one of my friends try on an Oxford shirt once and his response was "I already have a button down shirt". Slowly, but surely.

[alan]

Glock, who suggested the wardrobe makeovers? You or your friends? I really wish my "old man" friend (he calls himself that) would ask me for advice. He also never goes on dates... Ever. I think he's shy.

[nicholascrawford]

I ask because one friend of mine will go to BR and text me pictures of clothes. I'm writing back as fast as I can, but I keep telling him that I'd rather be there than sort through pictures from home. He says he wants me to take him shopping his spring, so I look forward to that.


Another friend views me with a tremendous amount of respect, and I've already taken him under my wing in the past. We painted his apartment, helped organize things the mess, spent $50 at the laundromat washing his clothes, etc. I told him that I want to take him thrifting, and he was open to the idea. He doesn't really have any money, so it would be at my expense, which I have no problem with. He just needs the help and is open to it coming from me because of our relationship.


I appreciate the input and agree that it can be a path fraught with risk.