I’m going out with an ex-boyfriend next weekend. I don’t really want to get back but I just want him to regret everything he did to me. What do I wear? — Ding-A-Ling
I Wish you’d elaborate on your question a bit more, but from where I’m standing, I’d say he was cheating or maybe lying like a rug to you.
I’m assuming he’s asking you out so that you guys can get back together, yes?
If that’s the case then I think you should let that twat have it. I hate to admit it but Marie’s idea with the cologne is brilliant in its subtlety. Actually, it really doesn’t matter what you’re wearing as long as you don’t look like someone that works at the back of The Pen after 10pm. What really matters here is sending the right signals. Which means you’re telling him that
you’re willing to get back with him. Or so he thinks. I’d say just get that boy all worked up and when he starts telling you how he loves you and how much he misses you, make like a shepherd and get the flock out of there.
Anyway, out of good manners, I think I should at least tell you what us boys like to see from the honeys. As a certain batty columnist from these very pages often says: You should look "fight"! That much I agree with.
But in the end, most boys won’t really know or even care about your outfit. And that, my dear, is the sad truth.
Scott
First of all, your conundrum tells me that you still want to get back with him. But I’m not a shrink, just a style shrink. So in order for you to screw up your life, think about everything he didn’t like about you. He called you uptight? Lose the three buttons on your blouse and wear a lacy black bra underneath. He called you loose (kind word for slutty)? Up with those buttons and snap up some of those horrid T-shirt bras.
He said you were too needy? Wear a suit and screw me heels in fire engine red. He said you were too cold and distant? Wear a sundress and smile. Now if he cheated on you for no reason or he just got tired of the whole thing…just wear his favorite scent on you and waft it towards his nostrils strategically (i.e. when he starts yabbering about those "Remember whens…"). Now go forth and don’t go crying back asking me what waterproof eyeliner to use when he dumps you again.
Zelda
Sneaky
Hmmm... tough one. So much so that I had to consult my uber chic writer pal Dino on the matter. He says, "It’s ok if they’re fairly plain and dark colored, like retro trainers, and the rest of the outfit is vaguely Boho as well (i.e., a turtleneck or a slim v-neck sweater underneath the suit instead of a shirt and tie)." Ho-kay, then. I think wearing a t-shirt would work here too.
Although he neglected to mention the cut of the suit you should be wearing, I personally prefer close-fitting suits, a cut I seldom see around here.
But the key item in this look is the sneakers. Dino was right to say that the sneakers have to be retro.
I would think that the Adidas Samba would work in this instance and not your Nike Air Max with pump up action.
And what about socks? Should you wear them or not?
Since you’re well on your way to committing sartorial hari kiri, I think it’s best you get the socks right. Instead of using athletic or dress socks, why not try colored socks or something with an interesting pattern? It might give your look a little something extra.
Scott
Unless you’re Marc Jacobs or Wes Anderson, the geek chic look only works if you really are a cool rich geek. Just kidding. However this is a tricky thing to pull off, like three-piece coats, suspenders and spectator shoes –- you can either pull it off or look like some sad choral boy. Brad Pitt did it once and it was literally the Achilles heel of his otherwise pristine career as a fashion god. However, Johnny Depp did it and strode like an unaffected peacock amongst the ruffled swans.
Black tie events already have their woes with losers mingling about festooned with cartoon character ties.
Black tie means, well black tie; it’s simply not the kind of shindig that’s open to interpretation (i.e. stuffy for those who regard themselves as adventurous). So I suggest that you get your best little tux on and charm that lady for an evening. Now a suit with sneakers can be worn in less formal events such as art exhibits, store openings or perhaps a special night of tippling. Try using charcoal or navy (maybe even with faint pinstripes if you dare) instead of black because black sort of says, "I’m deliberately doing this suit and sneaker look." Bad idea. Now whether you wanna go Euro heir (with a button-down shirt in a stealth wealth color) or American heir (with a logo t-shirt), make sure that the suit has a trim cut to it (very Dior Homme) and is a plus when it comes in a slick fabric.
Again, its either choral boy or style savant — this, my boy, is your wildcard moment.
Zelda