What to Wear II: Company Holiday Party

Dear Witty and Stylish Amalah,

Aack! You’ve gotta help me! I am 36 and way too old to not know how to dress myself properly, but old enough to know when it’s time to go crawling for help! My husband and I want to go to his company’s holiday party this year (held at Sea World, of all places, and they’re charging us for tickets! What’s with that?), and the dress is supposed to be “cocktail”. I’ve never had a cocktail, never bought a cocktail dress, and even if I had, it wouldn’t fit me anymore because I’ve lost 60 pounds in the last year. I don’t (please don’t pass out) even own one lousy pair of heels, because I’m 5’8″ and so is the hubby and I never go anywhere fancy anyway.
Pretty please, can you turn this pumpkin into a princess for one night? I dress OK for everyday mom-type stuff- think J. Crew by way of eBay- but I haven’t a clue how to play dress-up. I don’t want to look like an aging prom reject! I will do anything and everything you ask and even take before and after shots to prove that you are a fashion soopergenius.

D

Let me get this straight…a party…at Sea World. A cocktail dress…at Sea World.

Your husband’s company is a little weird. But! I am not here to judge; I am here to help! (Well, okay, I’m here to judge ugly shoes and outdated hair, but I judge ever so lovingly.)

So guess freaking what. You need a little black dress. Don’t be afraid of the “little” part — that really just means not floor-length and bedazzled and tulle-ed out the wazoo. Simple, classic and clean.

The good news is that it is PRIME LITTLE BLACK DRESS TIME right now. The stores are chock-full of them. (MY husband’s weird company threw their holiday party in January — right after all the party dresses from Christmas and New Year’s were pulled but before stuff for Valentine’s showed up. I literally had four whole black dresses to choose from in the entire DC Metro area.)

Since you don’t have that many places to wear your dress, I’ll do my best to suggest some not-too-expensive options…HOWEVER, even if you say “we never go anywhere fancy” I still think a good black cocktail dress is an essential investment, particularly if you pick a nice classic style. You’ve already lost all the weight (and you look FABULOUS, darling), so I see nothing wrong with buying something beautiful that you can wear for years and that maybe didn’t come from the clearance rack.

(Another perk to black dresses — as opposed to prints or bold colors — is that while they are striking, they are not ultra-memorable. Which means with different hair, shoes and jewelry you can probably wear the same dress to next year’s holiday party and no one will notice.)

From the photo you supplied, I’m seeing nice long arms and legs and a full bust. This means, generally speaking, you want to avoid dresses with teensy or no straps. V-necks and halter tops are Good, as are A-line skirts. If your bust measurement is bigger than your hips (which I cannot even begin to guess at), a fuller skirt is Good. If you’re about even on the top and bottom, a lovely fitted sheath dress would be To Die For. Skirt lengths should be just around your knee, and no more than a couple inches above it. That’s Prom Dress Reject territory, right there.

(No, I don’t know why I’m capitalizing randomly either.)

So. After much web-browsing and knuckle-biting because I have no reason in the world right now to buy a pretty new dress but OH HOW I WANT A PRETTY NEW DRESS, here are my favorites from the major chain-y type retail stores, priced high to low.

(I looked at J.Crew’s offerings, by the way, and yawwwwn. Your choices there right now are Boring or Bridesmaid. Wah.)

Lace v-neck dress, $168 at Banana Republic. SUCH a fun take on the simple black sheath dress. It’s like you’re wearing a little shrug over a strapless dress. And yet you could still wear this one for years and years, since even the new elements (a lace cap-sleeve overlay, empire waistline) are ultimately very classic. Love it love it love it. You would need a pair of high heels with this one — preferably something strappy or some black peep-toe pumps.

(Also, I WISH this one came in black. That style would be terribly cute on you. Keep that look in mind if you brave dress shopping on your own.)

Donna Ricco Cap Sleeve Silk Dress, $138 at Nordstrom. I love this dress, even though I could never wear it. That bodice would flatten me like a pancake. Oh wait, I already am a pancake. This is one of Nordstrom’s suggestions for the full bust body type and I have to agree — it draws attention to your curves without a lot of cleavage and the slight flounce of the longish skirt is very slimming for the butt and thigh region, if that’s a concern. Cap sleeves are flattering for long arms AND age appropriate. And the hemline keeps the dress from being boring and matronly. You could wear any type of heel with this — even a low kitten, if you’d rather not accentuate your height.

Cap-Sleeve Lace Spectator Dress, $119.99 at Ann Taylor. (Me and cap sleeves — who knew our love ran so deep?) This one is suspiciously similar to the Banana Republic dress, only it’s on sale! Whee! Not surprisingly, I don’t love it as much as the BR one (the construction around the empire waist doesn’t look quite as nice, although the model’s slouchy pose might be the real problem), but if the fit and the price is right, I see no reason why this dress couldn’t be your go-to party dress for years to come.


Curvy Jersey Faux-Wrap Dress, $89 at Victoria’s Secret. Prices plummet when you move from silk to knit fabrics, and you do lose a little bit of evening-appropriate dressiness. BUT you can balance out the casualness of the fabric with your accessories. Put your hair in an updo, wear dangling diamond earrings, carry a metallic or jeweled clutch. And heels. Definitely heels. Victoria’s Secret has a lot of nice jersey dresses (I’m also very fond of this one), and I think the faux-wrap would really accentuate your new curves and weight loss, without any of the downfalls that usually come when big-busted girls wear wrap dresses (cleeeeeeeavage, miles of cleeeeeeeeeavage.) Biggest con? Online shopping only, which means if the dress doesn’t work, you’ll have lost valuable shopping time to the postal service.

Isaac Mizrahi V-Neck Knit Dress, $39.99 at Target. Yes, even Target has a holiday shopping guide to Little Black Dresses. The Isaac Mizrahi line has an excellent selection of obscenely cheap, classic-looking dresses. Honestly, I saw this exact dress at J.Crew in silk for almost $200, and here it is at Nordstrom. Of course, you do get what you pay for in most cases. (This dress was actually my original choice for you, but check out the user ratings. Eeek.) But you know what? If you are on a tight budget and completely sure that you will never ever wear this party dress again, whatever. Buy a disposable dress that makes you feel super-cute and you don’t have to worry if Shamu spits fish guts all over you, or something. (Promise me, though, to wear FABULOUS heels with a cheap dress. Fabulous. Real leather, maybe with some bling. It’s all about mixing and matching your price points. Cheaping out on an entire outfit leaves you with a…cheap-looking outfit.) Another con here is the online-only thing, which means if the dress looks like ass in real life, you’ve still spent about half the price on shipping.

But just keep in mind what I said earlier about treating a good party dress like an investment. $40 on a dress this year that falls apart in the wash means if you get surprised again with a party or wedding invitation, you might spend $60 on a dress next year. At that rate, even if you wear this dress four or five times, those higher-up price tags really aren’t such a bad deal after all.