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Recently, Kyran sent me what has to be the Best Style Question EVER, primarily because her email was so eloquent and funny. She is asking for help for her husband, because, as she told him, "there have to be wardrobe options out there that are no-brainers for you and will not cause neighbors and potential clients to hand you a rake."
Here is a little excerpt:
Then one day, the boy left corporate advertising and came home to work freelance. He worked very hard, and the enterprise wobbled a while, then prospered. He worked out of an office in the house, during hours of his choosing, and only occasionally did he have to meet with actual live people. The boy loved his work and would eagerly sit down to his Macintosh computer in the mornings, still in his bathrobe and comfy slippers.
Gradually, the bathrobe began to stay on later and later. As time wore on, the faded & baggy levis, the x-large ts (worn untucked), and worn-in converse sneakers began to seem rather formal. One day the boy's wife saw him coming down the street toward her, and commented that he looked rather more like someone going door to door to do yardwork, than someone who worked in the field of design.
The boy rolled his eyes.
The wife was in a bind. She did not care to be a controlling wife who dressed her husband. She respected his desire to be comfortable and "himself", and to expend as little energy as possible into thinking about what to wear. At the same time, she felt that crewneck sweatshirts and jeans with the knees ripped out did not do justice to the brilliant light that was her husband.
To complicate matters, the boy was a southern man, and did not cotton to be told what to do. "For god's sake, grow up," would not work as a call to change. She would have to be crafty.
Kyran will be posting her full letter at Notes to Self; you really need to read it. And the rest of her blog, too.
Kyran has been culling her husband's wardrobe and throwing things in the trash, in a sort of kinder, gentler What Not to Wear scenario. But she has now tossed so many things that he is running out of clothes and needs to do some shopping.
The goal is not to get Kyran's husband into a suit but to move him back to the days when he wore clothes that did not make him look like a lawn guy, which Kyran describes as "levis and t-shirts and tennies everyday." That is a perfectly appropriate look for a self-employed designer who works from home.
Lawn guy, however, is not.
What should he buy?

Banker striped shirt, Old Navy, $24.50
Jeans. Of course. Because he's a creative type who works from home, jeans are fine for everyday AS LONG AS they fit properly (no sagging, please) and do not have holes in them. I would suggest a dark wash, as this is easier to dress up a bit than anything lighter. If he complains about the new jeans being "stiff" (as my husband is wont to do) Kyran can launder them with some fabric softener for the first few washes. Or she can tell him to suck it up and stop complaining. Which is usually what I do.
I am all heart, I know.
Chinos. You know, khakis. Yes, really! My husband was a diehard jeans guy for YEARS, until one time when we were traveling, he was compelled to wear his khakis to fly. And at the end of the day he said to me, "Those are SO MUCH MORE COMFORTABLE than jeans." Which of course I had been telling him for years. Soft cotton khakis are the perfect casual pants -- they still look great, but they're not binding or stiff. Go for a flat front, if you can, for the slimmest line (my husband still insists on pleats, if you must know, which makes me insane, but at least he's wearing nice pants).
Tees. I'm really going out on a limb here, aren't I? But there is nothing wrong with a really great tee, AS LONG AS it fits. Kyran describes her husband this way: "Our hero is 44 years old, about 5'10. While he grows only more handsome and














