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I am attending my cousin's daughter's wedding in September, a formal evening affair to which I need to wear a floor-length evening gown. There is also a cocktail drinks event the night before, a function to which I should probably wear something OTHER THAN my regular clothes.



Obviously for this shit, I need clothes that I don't currently own and I will have to perform gender in a way that I have spent my entire life avoiding.

Is it drag? ... Probably not. It's more like inverse drag. I don't make other people uncomfortable or challenge their expectations when I dress up like a girl. I make myself uncomfortable so that they feel at ease.

Could you just wear a tux? Would that be OK?

No. While the fam is pretty cool and formal attire is the key here, a tux would generate a shitton of questions that I would have to answer in the negative. (I do not identify as trans, non-binary, gender-questioning, butch lesbian, whatever.) I am merely a late-middle-age straight lady who doesn't like dress up clothes for women. That's not a heavy enough weight on the scales to justify wearing a tuxedo to my cousin's kid's wedding.

Also, it is true that finding dresses that fit my body is a lot more feasible than finding a tux that fits my body. Wearing dresses will not embarrass my mother. *sigh* Girl dress up clothes it is.

How about a flow-y pantsuit? I am built like a short-waisted fertility statue, but with less tits and longer legs. Definitely an ass you can set a table on, though. I am NOT a flat-assed white lady. Black men admire my ass, ffs. Pantsuits are a fashion mistake for me, flow-y legs or not. Also the invitation says floor-length gown on the very fancy paper. There are expectations to be met, here. :)

I am not a wearer of dresses or makeup. Like, ever. Makeup feels weird and gross and it's all perfumed, yes, even the setting powders and shit, and I just... no.

Dresses have many features I do not like (ruffles, lace, fake fabric roses, flounces, ruched fabric, anything chiffon, pleats that are too small, feathers, sequins...) and require synthetic undergarments (slips, foundation wear) that I do NOT like, it all feels like plastic touching me, why does there have to be so much fucking plastic?

That said, girl dress-up is the most reasonable option of the available options so... it's gonna be girl dress-up.

Happily I am at the age where "classical" is a possibility because there are a bunch of other middle aged ladies who want something that's not overly fussy. Fewer fake fabric flowers, less lace, a reduction in ruffles, a paucity of pleats. There's more likely to be an emphasis on good drape, simpler construction, looser, more forgiving fit and so on. Grown up dress-up, as it were. Princess seams can die, die, die.

Why are you even going if you hate dress up so much?

I am in part attending this function to serve as my mom's driver (I'll pick her up in Harrisburg on my way east) and to facilitate mom and her sister Charlotte's subsequent visit at mom's house following the wedding. Charlotte lives in Alabama. Mom lives in Pennsylvania. Due to geographic realities, they don't get to see each other that often and they're both in their eighties.

Mom visiting with her sister Charlotte is important enough for me to do drag for the weekend so's to more or less fit in with the other people at the function. Also, it's Gloria's wedding and I respect her vision for the event (she is an event planner by trade) enough to fucking make an effort on the outfits.

So, it's time to play Dressing the Chunky Middle-Aged Lady Who Hates Dress-Up and Has Sensory Issues With Dress-Up Clothes.

Cocktail event: It's evening in mid-September in Philadelphia. I need a little black dress style of thing (need not be black, but should be urban cocktail-party attire) that makes me not look like a sausage and that I can sit and walk in.

Wedding event: Evening in mid-September in Philadelphia. I need a floor-length thing that looks elegant-ish and can be walked in comfortably.

Style constraints...

Sleeves: I like 3/4 length sleeves. I can do sleeveless. I do not like full length sleeves. I have excellent shoulders and upper arms that are not flappy with age (yet).

Neckline: I have exceptional collarbones. Neck not overly crepe-y for 56. It's OK to do boatneck, sweetheart, etc.

Cleavage: 7UP. (Never had it, never will.) I do not need exceptional support but if the dress is off-the-shoulder, I will need to buy some sort of bra or stick-on pasties to go with it. Dress should not structurally depend on boobs. I do not have enough boobs for them to have any sort of structural involvement in the dress.

Overall styling of dresses:

No lace. Non-negotiable. Overlay lace is also no, in case you were wondering.

No ruffles.

No sparkles, fake flowers large or small, tiny pleats, chiffon, or feathers.

No asymmetrical hemlines.

No pencil skirt or mermaid skirt. Skirt MUST be full enough for normal walking, no slit.

No Empire waisted anything, they look like hell on me.

Nothing above the knee, no slits.

Styling OK things: larger box pleats, tea length, some non-ruffle drape, low back, open back, shoulder straps from spaghetti to broad, single shoulder, halter neck. Can be a "need help to zip" dress. Fitted torso OK, fitted hip-ass-thighs NOT OK.

Dropped waists work really well on me because they normalize proportions. Pity they're not currently in style.

Is used OK? Yes. I'm not "on a budget" but I will 100% go cheap if I can. Used is fine.

I need shoes for all of this. These will have to be flats or low heels because I cannot walk acceptably in high heels.

Do people still wear nylons? Are nylons still a thing? (I hate nylons, 100% willing to skip nylons with tea-length cocktail dress and floor length evening gown.) Floor length evening gown might well have me wearing nude-color socks with my mary janes, you fucking watch me do it, LOL.

I need accessories (my friend Lala has accessories for days) so that I look like I'm not naked. (I do not own or wear jewelry or accessories. Not at all. Nothing.) Probably a necklace and maybe some earrings or something. Bangle bracelets don't work because they do not fit over my broad-ass working hands. I could do a clasp bracelet if I had to, but I hate shit on my wrists. Hard pass on the wrist adornments. Not wearing rings either. I fucking hate jewelry, honestly.

I just realized I'm going to have to shave my armpits for this.

Oh, and I probably should not shop too early because I'm losing weight for realsies under the "Thou Shalt Not Consume Fat" model of eating. I may be a rather different size by September.
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