FASHION POLICE 101 or "How to Tell Someone You Love You Hate Their Outfit"

So I have this friend...

Hold it right there, I know what you're thinking: this is the oldest plot device in the book, used in every third episode of The Brady Bunch.  This is not about Cindy's friend, it's about Cindy.

I am shocked at your disbelief, readers, shocked.  Next, you'll be telling me that I don't have an identical cousin, when that rumor has been put to rest again and again, and again.

But back to my friend.

He's not the most stylish person in the world -- in fact he's something of a slob -- but he does know what goes with what, and has been a follower of fashion for many, many decades.

Now, the man he shares his life with is arguably much neater than he. But it's the what-he's-neat-with that's the problem.

You see, the partner of my friend has a tendency -- some might say a  compulsion -- to wear clothes that are alternately too large (baggy twenty-year-old pants), or too tight (think former Olympic gymnast Mitch Gaylord), or too something (over-bleached acid-wash jeans)  And while there's nothing wrong with mixing patterns occasionally, said mixing requires a great deal of care and skill, and an eye, readers, an eye -- or so my friend believes.

The problem my friend has is what to do about his admittedly-judgmental-sounding opinions.  You see, he believes -- with good reason, it turns out -- that his partner will sometimes intentionally mismatch patterns or otherwise dress provocatively, solely to push my friend's buttons.  He (the partner) told him (my friend) as much!

My stylish-if-slobby friend, in contrast, happily solicits others' advice and is open to receiving it, never interpreting it as threatening or challenging or nobody's business but my his own.

Stylish and sophisticated readers around the world, have you ever found yourself in my friend's cute-if-scuffed shoes?  If so, how do you handle it?

Some of you will say that if you love someone, as I know my friend does his partner, that you accept them as they are, end of story.  Some, perhaps with a few years of psychotherapy under their belt, might even argue that the problem is my friend's and only my friend's.  He is the one who is seeking to control another by criticizing his partner's choice of outfits -- never a healthy strategy in any relationship.

Some might say, moreover, that personal style is entirely subjective and that what my friend thinks looks unflattering on his partner, others will find just the opposite -- that there's no objective truth to what looks good and what does not, beauty being in the eye of the beholder and all that jazz.

Then there will be other more empathic souls who know that adults who dress themselves poorly need guidance and are only inviting the criticism of others.  Better that the loved one offer constructive criticism in private than a stranger his 2-cents in public.

In closing, readers with no-doubt highly-honed, read-between-the-lines abilities,  I ask you:

Should you tell someone you love you don't like what they're wearing (with the confidence that you know what you're talking about) or shouldn't you?

How do you handle giving advice to someone you love, when no advice has been solicited, and it might make them feel criticized?

Or if you don't give unsolicited advice, do you just keep quiet, offer (at most) a none-too-subtle, up-and-down look of dismay and leave it at that?  Do you ever ask if the person is open to your opinion, knowing full well that the very question suggests disapproval?

I need guidance -- to share with my friend of course.  Crimes are being committed.

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