Since I'm a fashion Designer, men always ask me for advice.
From "How would you dress me?", "What do you think of this T-Shirt?" and "Am I stylish enough for your taste, I mean you're the expert...?" to outright "Would you take me shopping?" I get all that and everything in between. I don't remember one man, not one single guy who didn't ask at least once at one point -- usually in the beginning.
Now, I live in a stressful, competitive and quite snarky career environment, where it is way too easy to commit a style faux pas.
Even after 20 plus years in this business, there are days where I am totally intimidated to go to work. I change my clothes 15 times, like a teenager before a first date. And then, as soon as I arrive, I wanna run back home and change again.
So, I understand why guys don't know how to dress. How could they? What's out there isn't very interesting or creative because most men are just as scared as me to be the butt of a joke when they dare to choose something that is a tiny bit different.
I love men in (well-fitting) suits. It's the hottest look in my opinion -- manly, strong and confident. But after a time period where I wore men's suits myself, I know how uncomfortable and stifling that can be.
So, what else is there? Euro-Trash? Hmmm. No. Not really. Surfer duds? Depends on the guy. If they are obviously not surfers, it usually doesn't work.
The man in my last long-term relationship dressed really understated, expensive and stylishly unstylish. I liked that look, but all that black drew a lot of glee and jokes. Shopping with him was a many hours nightmare and I never wanted to be in his (always cool) shoes, witnessing the agony and fear in choosing his outfits.
If it were up to me, I would drag my man to Traffic in the Beverly Center. Everything there looks so fucking cool and tasteful, and even though the merchandise there is definitely geared towards gay costumers, there are hundreds of pieces that look understated and sexy and as long as one steers away from the ruffled shirts and jewelry, it all works to bring out the best in a guy.
But in reality, guys are clueless and like I said before, I can't blame them.
My friend's ex husband used to dress in shorts and little T-Shirts and at 5'3" that wasn't a good look for him. She bit her tongue until he showed up one day in very short red shorts with a red T-shirt and she finally said to him that he "looked like a stereotypical color blind computer engineer at the company picnic." They are divorced now...
My other friend's boyfriend wears tasseled loafers with unbuttoned lose shirts and if he wasn't so young and hot, he could easily slip into "Carpet Salesman" territory. So, who cares?
I also don't care that my cute sometimes-date always wears lumberjack shirts, no matter where we go. He pulls it off with height, youth and so much intelligence that I don't mind, specially, once it comes off.
What I will run from: that ugly, uninspired uniform of a beige pant with a navy blazer. "nuff said.
So, now what about too small concert T-Shirts or shirts with gas station logos? That's a little tricky, personally. It falls into the same category as women over a certain age in Daisy Dukes and cowboy boots.
But if that T-Shirt is a sentimental item and means something to the guy? My (painful) experience with that is, that I wish I'd headed my own advice of "Shut the fuck up!" In the end what does it matter?
There is one exception to the T-Shirt with a message or print on it:
Todd Bemis's legendary "Mickey Mouse on the Cross" Shirt. This design is so genius that it overrides all my other rules and dislikes.
Even I wore that shirt and would again wear it if I only could find it. The only picture I have of it is my three-year-old daughter in it. If this isn't the cutest and funniest shirt ever, I'll eat my (plain) black T-Shirt.
HuffPost Lifestyle is a daily newsletter that will make you happier and healthier — one email at a time. Learn more