1. Saying something critical and mean to a guy might get his attention but not his admiration. I have known generations of women who said mean things – I only realised, sometimes years later, that they actually thought they were flirting. We are not praying mantises. We do not want to mate and then be eaten.
2. A nice, plain look really says that you have nothing to prove. I love the way the women look in Berlin, as if they had heard rumours about fashion but didn’t quite believe them. Fashion isn’t style. Style is about independence. Fashion is about following.
3. I’m always impressed by women who are big tippers. Of course tipping is American, but generosity is universal and generosity in a woman is a marvellous thing. As a former waiter and bartender I have found women to be below average in granting gratuities. Everybody loves a babe who picks up the tab once in a while or maybe sticks a twenty in your garter.
4. Guys who get around more than I do these days tell me that, if a woman is going to get tattooed, she shouldn’t do it on her back. That spoils the abstraction of the downward-facing dog and distracts the imagination from wandering. Do the bellybutton area instead, maybe. Or, if you must do the back above the butt, don’t do an arrow pointing down, but maybe have your anniversary date tattooed there.
5. When considering a tattoo, just think: “Would I have liked this on my grandma?” Because someday you will be your grandma.
6. If you’re going to wear jeans that are all ripped up, especially around the knees, wear plasters underneath the holes.
7. If you’re thinking about getting that date-rape nail varnish that tests drinks for Rohypnol, etc, you’re doing something wrong. Maybe you should get a little pistol instead.
8. I’ve always thought that some underarm hair was sexy. Sarah Silverman’s might be a bit much, but I like the gesture. It says “born to be wild”. I also like that she pulled her vaporizer pen out of her clutch while doing the red-carpet meet-and-greet at this year’s Emmy Awards. “This is my pot,” she said. “It’s liquid pot.” Very ladylike.
9. Beautiful women should just get more beautiful. Daphne Guinness is 47 and still on the upswing, baby. Now she’s a rock star.
10. French manicures with the little white tips make you look like a porn star. Which I suppose could be okay if you can carry that off to its logical, uh, culmination.
11. Porn is a business worth $14 billion annually. Mostly male audience, I reckon. Imagine if women started watching it, too. Heh, heh. They would know more about what they are quietly being compared to. Actually, I don’t dig porn. I don’t watch it in the same way that I don’t watch professional golf on TV. But if I wanted to learn how to play golf, I would certainly watch Tiger Woods and Rory McIlroy for pointers.
12. Guys don’t like the slutty look unless it’s 100%, which you might as well forget about if you’re reading this, or 5%. Sluttiness is best admired from afar, unless you have the rare ability to add just one little trollopy touch or oversight, just that one thing that’s perfectly wrong. That’s a turn-on. Pick one! Chewing gum, chewing a toothpick, wearing an ankle bracelet, a G-string showing (lorry driver’s butt, plumber’s butt in American), a prison-like badly drawn tattoo, push-up bra, strap showing in back, teased or ratted hair, no underwear, jeans skirt, Velcro, man’s white shirt tied at the sternum, gold bamboo earrings, leather trousers, jewellery with your first name on it, trademark-logo jewellery, obviously fake bags or the bags they imitate. As a Las Vegas casino commercial puts it, “Just the right amount of wrong.”
13. A well-fitting Ramones T-shirt really looks good on a good-looking woman. A big sports-team jersey really looks bad on any woman. Only wear a baseball cap if you really, really would rather be Jennifer Aniston.
14. I see so many pretty girls who would be beautiful if they weren’t trying to look like Kid Rock. I find this really hard to understand.
15. Anachronism is cool if it’s really well done, like Amy Winehouse’s hairdo. Better to look like the Ronettes than Gaga. We can only hope the future looks more like the past than futuristic.
16. It’s better to retire the midriff sooner rather than later.
17. On the other hand, a schoolgirl thing can be pulled off by the trim of figure for years – kilt, blazer, white blouse, saddle shoes.
18. It’s better if we can’t tell what brands you’re wearing – 99% of hetero men don’t want to know. If the name is on the outside, with the possible exception of a handbag, that’s too much information.
19. Wearing something slightly menswear is cool. Like a shirt with a monogram, oxford shoes, socks, khakis, tweed jacket.
20. Wearing something slightly lezzy, like a Joan Armatrading or Tracy Chapman T-shirt opens up the playing field and makes the imagination a little itchy.
21. Dudes dig bobby pins (hairgrips?) and headbands and braids. Hate scrunchies, especially cute ones. Cute is overrated.
22. Don’t come near me with Hello Kitty.
23. Not everything on your body has to be perfect. If you saw Kate Moss in a sweater with a moth-hole in it, you might think it was Maison Martin Margiela and the weaver put it there very carefully, but a guy is going to think, “What a down-to-earth chick.” Frayed collar and cuffs are good. Not distressed but personally worn-out.
24. The only reason I tolerate flip-flops is that I’m a foot fetishist.
25. Headscarves are good if worn daringly, like a Teherani vixen courting a hair ticket from the religious coppers. Or incognito style, like Jackie O, with big sunglasses.
26. I always thought that smoking a cigar looked affected until I saw Sofia Coppola smoking a Churchill while walking a dog and suddenly it looked effective.
27. Don’t always wear the same perfume. Mix it up. Half a left-brain scent and a right-brain scent, a fragrance of yes with notes of never.
28. Sorry, I know you want to look exotic, but nose rings always make me think of boogers.
29. Slim, snug dress, heels, bun with a pencil stuck in it.
30. Never wear bike shorts, or any kind of dedicated bicycling gear except bicycle trouser clips.
31. Running shoes are for running. The neon sci-fi ones are hideous. If you wear sneakers, wear something that you might have played tennis in or gone boating in, say in 1964.
32. If you borrow a guy’s razor, change the blade afterwards. If you borrow his toothbrush, don’t tell.
33. Don’t say one-piece or tank suit, say maillot[itals]. Alternate with bikinis for interesting intersecting tan lines.
34. If you have to wear a hat to a horserace, it should be smaller than a horse’s head.
35. If you’re going to an art fair, resist the temptation to wear a clown suit and wear a nice dress or jeans and your most expensive high heels instead. Leave humour to the art.
36. If you really can’t decide just think, “What would Tilda Swinton do?”
By Glenn O’Brien