Don't forget to write a 'thank you' note

With the holidays coming up... any thoughts on attire for Thanksgiving dinner/meeting the boyfriend's parents for the first time and/or a first trip to Christmas Mass with the aforementioned boyfriend's parents? My boyfriend claims he is likely to wear his admittedly boring uniform of khakis/button down shirt/sweater, possibly with a blazer, definitely without a tie. This is a no children zone, just his parents, his older sister and her husband and possibly some family friends. The setting is Weston, CT.

Weddings, funerals, interviews, functions where colleagues' wives will be in attendance, meeting the boyfriend's parents for the first time on a major holiday -- all of these special occasions require careful outfit premeditation.

And in some cases, for those whose wardrobes, regardless of venue, regularly veer toward the tarty, the sloppy, the inappropriate, the in-your-face political, or the just plain stupid, a healthy, take-one-for-the-team sense of compromise must also be closely considered.

Why?

It's simple. In these situations, the clothes you wear must not negatively distract from the good impression you're presumably hoping to make. No one's asking you to act like "the little woman," fake interest in 'Frontline' or laser-off your Dick Cheney neck tatt, but you have to understand, especially in the case of meeting your significant other's parents for the first time, how you carry yourself into and inside the family home is likely to remain in Mom and Dad's minds (especially Mom's) long after the initial introduction. Don't get me wrong, I'm not saying your outfit will be the sole deciding factor in whether future conversations between parents and son conclude with a genuine "Please send _____ our love" or an obligatory, "Give _____ our best," but I am saying you don't want to jeopardize your chances of being in their good graces just so you could feel more "yourself" in your favorite slouchy low-rise jeans, UGG boots and Harajuku Lovers hoodie. If these are formal people who like to host a formal Thanksgiving dinner, dress accordingly (see below), drink accordingly (a glass of water in between every glass of wine/beer), act accordingly (no grabby grabbingtons under the table, to start) and please, please write a thank-you note as soon as you return home.

If you don't know what the implicit dress-code will be, ask. And then ask again when he's not playing 'Guitar Hero III: Legends of Rock.'

Dysfunction has a way of infiltrating every family dynamic around the holidays, so do everything in your power not to invite controversy with a potentially controversial look.

Outfit Guidelines:

(1) No casual cuts/fabrics -- even if they're your best $247 Sass & Bide trouser jeans or your most luxe $200 Juicy Couture velour track jacket, I can guarantee you a Mother who breaks out the good China for Thanksgiving dinner will only see jeans, sweatshirt and disrespect

(2) No cleavage -- not even a hint (no, no, no, no and no)

(3) No skirt/dress that hits higher than two inches above the knee -- remember, when you sit down for post-dinner Brandy on the heirloom divan, that hemline is gonna creep up an extra few inches and potentially give your in-laws-to-be a nice little "view" of the crotch of your control-top hose

(4) No sky-high stilettos -- believe me, if I'm saying put the vixen heels away, I really mean it. Statement heels have no place at a sit-down dinner among new family members in the suburbs.

Outfit Recommendations:
(1) Sweater dress, tights and flats
(2) High-necked blouse, trousers and Mary Janes
(3) Dressy sweater, wool skirt and low-heeled boots
(4) Basic shell, wool jacket, slim pants and flats
(5) Long-sleeved wrap dress in a muted color*, tights and round-toed pumps

*have your tailor sew up the bustline to just above where the "cleave" begins to form