Stylists, assemble!

December 17, 2012 12:30 PM

Help me dress myself for a hot date! Dress to follow.

Armchair stylists, I need your help. My husband and I are going out to dinner on Thursday, to a very nice restaurant in Boston, to celebrate the end of my semester and to spend some of his bonus. So a classy place, after which we will go out for drinks (similarly classy place) and then back to a hotel for some (coffee willing) extensive lovin'.

So the look I am going for is classy and sexy, in a sort of "look what you get later, ah but you don't get it now" way. I have rented a dress (Rent the Runway, the front, the back) and want to know what else to wear. I can't just have that cutout back visible in the restaurant...or can I? I'm thinking red or black heels, and then should I do a black blazer, or a black or red wrap? Help? And then sort of "regular" evening makeup? Or something more?

FWIW, I am a 20-something white woman, brunette, average height, a touch thin of average, small bust, and hips-but-minimal-ass.

posted by anonymous to clothing, beauty, & fashion (22 answers total)

I'm just a dumb man, but isn't the back cutout, like, the point of the dress? I'd say either black shoes and a white wrap, or black shoes black, short blazer.

I don't know what evening makeup is.
posted by cmoj at 12:40 PM on December 17, 2012 [1 favorite]

That should look great on you! I'd be comfortable with a black pashmina or a chiffon wrap, only because it can be chilly even indoors. I wouldn't do a blazer, too businessy and the dress is so pretty.

Black heels, red would look trashy (sorry, just would) and you're going for elegant. Do regular makeup, minimal cheeks, charcoal/smokey eyes and a bold, red lip.

Done and done.
posted by Ruthless Bunny at 12:43 PM on December 17, 2012 [12 favorites]

I don't think you have to cover the dress with a blazer.

If you want to cover it, I wouldn't wear a red wrap with this dress. There is something about red and black that looks harsh and dated (in my opinion). I wouldn't wear a wrap at all with this dress. This dress is sleek and edgy and in my mind, a wrap doesn't "go" with it.

If you want to cover it, a trench coat (always chic) in a dressy fabric (like satin or taffeta) would look best in my opinion. Wear the jacket on the street and in the taxi. Take it off while dining. Fake fur would also be good or any other "evening jacket" that matches the vibe of the dress.

I would avoid red pumps and choose a dressy evening shoe in black or metallic.
posted by Fairchild at 12:51 PM on December 17, 2012 [4 favorites]

I think the right blazer would be very in keeping with the Halston look. Has to be the right shape, narrow lapel and in a fabric with some drape like silk; no bulky stiff wool, think YSL Le Smoking jacket. Color or black would work, and hopefully it has some detail that reads evening, like velvet or a touch of beads or sequins. Contrary to what cmoj says, I don't think it has to be short, but it will depend on your own proportions and where the hem of the dress falls on you - if the dress is short enough the jacket can be longer and it will look super chic. This will be a versatile piece to own because it can be worn to evening business events with a pretty blouse and pants, over other dresses, even over nice dark skinny jeans with heels for a more casual night out.

I think wraps on the other hand look frumpy and mother-of-the-bride 90% of the time. Obviously opinions vary, bring the dress out shopping and see what works.
posted by slow graffiti at 12:52 PM on December 17, 2012 [4 favorites]

I would try not to cover that gorgeous dress up if at all possible! A coat and pashmina for outdoors of course, but hopefully the long sleeves of the dress will keep you warm enough indoors.

I would keep everything else really minimal. Simple heels, very simple makeup, undone hair and minimal accessories. Go for that Kate Moss, hot-and-hardly-trying look. You're going to look great no matter what though! That dress is awesome.
posted by Katine at 1:01 PM on December 17, 2012 [1 favorite]

No blazer unless it's sleek and perfectly fitted, or it wouldn't look quite right. I personally think pashminas are a little dated, too. You could rock the dress alone, which I think would be best.

Heels either black or smokey dark metallic, this classic pointy 3" pump would read sharp and seasonally appropriate, unlike the sandal in the photo.

Either simple cat-eye liner with a bright lip, or smokey eye in a neutral non-black shade (bronze or smoky purple are nice) with a lighter, your-lips-but-better lipstick color. My color of choice is NARS lipstick in Dolce Vita.
posted by rachaelfaith at 1:02 PM on December 17, 2012

It's Boston, so you can wear whatever you want.

If you cover up the back of the dress, it's just another black dress. No blazer. No wrap.

Keep it simple: Black dress, black hose (not tights), black heels. Preferably a pair of shoes that you already own, are broken in, and you can walk in. Maybe one piece of statement jewelry.

Red shoes are hard to pull off, and red and black is also hard to pull off. You need to have an amazing sense of style and je ne sai quois to wear red and black and not look like you're wearing a costume.

I like a bold lip on a bare face, but wear whatever make-up works for you.
posted by ablazingsaddle at 1:03 PM on December 17, 2012 [1 favorite]

I love a silk indoor coat, and have a couple, but they are hard to get these days, if you could find one, it could be a pastel color or white. The person who suggested a white wrap with an all black solution is genius. Very elegant and not at all mother-of the-bride. But the wrap has to be huge, for it to be elegant. It's your coat, and you fold it up and either hang it or place it beside you while eating and drinking.
And don't overdo the makeup. You are probably gorgeous already in your husband's eyes. Evening, not TV. Match it to your eyes.
What you should work with in advance is getting your skin all soft and nice to smell. If you don't do that already.
Have a great date
posted by mumimor at 1:03 PM on December 17, 2012

Definitely no jacket or wrap. I would wear opaque tights (I think black or burnt orange or something would both work) and funky high black heels. Not boring pumps. Dark eye makeup, neutral lips, don't be afraid of blush.
posted by Go Banana at 1:06 PM on December 17, 2012

If you'd like to wear a wrapl I'd avoid red and go for a translucent black, material it would offer glimpses of the cut outs and not hide the drama of the great dress just soften it a little. I'd avoid anything too lacey just simple black, but as the night progresses you can remove the shawl/jacket say when you are out for drinks to help build up the sexy drama. Also a silver or gold metallic colour could work. Honestly though I'd wear it without anything over the top.

Black shoes would look good, a lot of shoes at the moment have a metal tip on the toe (a cap toe) which adds what I think is a nice detail if everything else you are wearing is black. Coloured tights are fun and popular at the moment.

If you want a coloured shoe why not try a colour other than red, a nice teal or dark purple pair would look really good and a little less obvious.

Also I'd go a smokey eye only if you know how to do it right, it would look amazing with it but a badly done smokey eye just looks like you've been punched and a strong lip colour.
posted by wwax at 1:09 PM on December 17, 2012

That dress is gorgeous. I've been thinking about it and I think because it's so simple otherwise you don't want to do too much to interfere with the style. I think a tuxedo type blazer would look good, but you're just renting it for the one night, you probably want to show it off.

Black or metallic heels. Black will look great, but I am totally seeing it with like a gunmetal metallic-type thing. Don't do red. Black and red can really easily look really harsh and kind of seems...obvious if you don't have another neutral in the mix.

I really don't think there's a wrong answer with the makeup -- a simple, basically bare eye (with lots of mascara) and a lot of red lipstick, a smoky eye with nude lips, or just a really "natural" face could all look great. I think whatever makes you feel the hottest is the way to go makeup-wise.
posted by SoftRain at 1:12 PM on December 17, 2012

One upside to a wrap or demi-jacket of some sort: when your husband helps you out of it before you sit down at the restaurant, he'll get the full SHAZAM! reveal. Could make for an interesting effect on him. Wink.
posted by nacho fries at 1:14 PM on December 17, 2012 [4 favorites]

Backless dresses are fine in fancy Boston restaurants. No worries except maybe about being cold.

Enjoy!
posted by Sidhedevil at 1:20 PM on December 17, 2012

Red shoes would be okay if they were burgundy or another shade of deep dark red.
posted by elizardbits at 1:55 PM on December 17, 2012

I think a dark purple pashmina would be lovely with that gorgeous dress. (Thanks for turning me on to Rent The Runway!) A deep, saturated purple looks good on many complexions and is just a tad more interesting than black. You could even coordinate with some sexy matching undergarments... I'll nth the black shoe suggestion. It's the most fool-proof way to keep it classy.

Have fun!
posted by yogurtisgenocide at 1:56 PM on December 17, 2012

I actually think you pretty much wear whatever you want with this dress and it will look great. It's simple and black so you can tailor the rest of the outfit to your tastes.

I would probably skip a red shoe - echoing those who mention it can feel dated sometimes to do red and black - but I love the idea of a real statement shoe with this dress. I'd suggest something strappy to echo the cut outs in the back and contrast nicely with the covered up-ness of the front. Metallic definitely could work, even a pattern or an unexpected color. I'm not sure what your taste is, but these seem classy but fun if you want something sort of traditional with a twist. http://www.zappos.com/bcbgeneration-lin-nude-blush-black\

A blazer would also be ok if it's a nice, sophisticated cut, but I'd just throw on a great tailored coat or trench and, once in the restaurant, take it off and rock the dress in all it's glory. It's sexy but still appropriate - no need to hide!
posted by amycup at 2:33 PM on December 17, 2012

No no no to the pashmina/wrap idea. They're super dated, too old for you and totally at odds with the sleek, modern vibe of the dress.

The back cut-outs will be fine in a fancy restaurant, but if you're worried about being cold then throw a trench over the dress on the way to and from.

I personally love red pumps with a black dress - black with black can be too drab, in my opinion. But if you choose coloured shoes, don't wear black tights. If you want to wear black opaques (which would probably be my choice given the weather), wear black shoes.

You don't need to accessorize too much with a dress like this - let it be the star.
posted by RubyScarlet at 3:59 PM on December 17, 2012

Of course you can go backless in the restaurant, the restaurant isn't your office.

Can you go braless? If not, you need a backless bra either with a silicone back strap (less good) or a plunging back. You may also be able to tape or pin the back strap into place, but that will ruin the undressing process. In case it isn't obvious all your underwear must be black, and seamless. Lace panties will obviate the VPL problem. A thong may give you a cottage cheese effect and I'm tired of watching ladies' thongs go by in a "look I'm so discreet" way. Lace shorts will serve you better.

Also get fine-gauge fishnet hold-ups (more impervious to damage than sheers). On no account wear sheer black hose - snag city. Black fishnets, flesh tone fishnets, or flesh tone sheers only. Suspenders are going to show all lumpy through the fabric, and probably also have someone's eye out in the event of sudden and temporary detachment. For security, you can carry an evening bag with a spare pair of holdups in a heavy DL envelope.

All your accessories must be black, white, grey, dark brown, or metallic. Do not add colours to this mix.

Shoes, if not metallic, should be fabric, not leather. Make sure they are so comfortable that you don't even remember you have them on. This is not the occasion for anything fussy or fragile. Killer heels are such an amusing idea, until you try to walk in them. No open toes in winter please, kthx. But also not boots, at least not indoors. If you need to wear winter boots and change them, strongly consider jewelled ballet flats which are compact enough to fit in pockets or an evening bag. Also carry a tiny bottle of 4711 cologne which you will apply in the bathroom to counteract stinkfoot after changing shoes.

Get a wristlet evening bag so you can keep your hands free. Also get a handbag hook so you don't need to fiddle with it. Again, no leather.

I'm visualising white crystal earrings, either studs or drops. If you wear a necklace make sure it matches the earrings. Watches aren't worn in the evening, you are being entertained and are careless of the time.

There are various smoky eye tutorials but you want one that's fairly smudgy, for resilience. It has to start off looking good the way it is going to end up. I recommend you make sure to curl your eyelashes (clamp the base, then the middle, then the ends, then do the other eye, then clamp the base of the first eye's lashes for 10 seconds or as needed, then the second's). Take the primer from L'Oréal's waterproof volume mascara and follow it with their 4-dimensional mascara, wiggling the brush from base to ends for just one coat. Comb out your lashes with a lash comb. Don't bother with false lashes, as they are another source of indignity in the undressing process.

Buff your cheeks with a fairly natural blush - try painting on a 2-inch wide stripe of too much blush along your cheekbones. Then take a cotton ball and buff it till it looks just right. Powder everything down so you don't have to worry that it will wear off.

Lips, just a little natural shiny gloss, the kind that comes with a wand. Make sure it is moisturising. After you apply it, close your lips around your finger and slowly draw the finger out, so that you won't get it on your teeth. (For FSM's sake, don't do this at the table.) Carry the gloss in your bag, of course, because no lip color will last all night. You are only wearing the gloss for balance. Lipstick is offputting because it looks just not kiss proof at all (as does makeup in general which is why we're only doing smoky eyes and sticking to natural blush). A natural color will still be good when it's half chewed off. Also carry a travel toothbrush in that purse, which is growing to monstrous proportions in the background with every recommendation I make.

Get a natural manicure done professionally. Nail polish wants to chip and make you look like a cheap tart that caters exclusively to clowns. (Or that could be just me.)

Look for a black wool coat with a dramatic faux-fur collar. A hat that looks like white Russian fox is good if you need it for warmth, otherwise, skip it. Your hair should be up in a simple style that is exciting to unpin (google for tutorials) and must be set with a firm but sparing spray of Elnett - no other hairspray is good enough. If you do wear a hat, practice the hairstyle with the hat first to make sure you're ready for any dislodging when you take the hat off. If you have bangs, sweep them out of the way with a bobby pin before you put the hat on, and take it out and stow it in the inside band when you take the hat off.

You could also get some gold or silver glitter hairspray and give yourself a conservative spritz over your hair, face, and shoulders. A little goes a long way and is spectacular.

You should keep warm with a pashmina. If you can't find funds for a real pashmina, a market stall one that is black with metallic, and very paisley and Anna Karenina, is a good trend and will get you through.
posted by tel3path at 4:22 PM on December 17, 2012 [4 favorites]

p.s. you could also wear black opaque stockings with metallic shoes. Test them to make sure the garters stay out of sight when you stand, sit, and move around.
posted by tel3path at 4:24 PM on December 17, 2012

Absolutely second slow graffiti, and agree on playing with hemlines - just wanted to call your attention to the shape of the blazer pictured in the link. With a bodycon dress, you don't want a similarly fitted, nipped-in jacket (competes with the dress; looks 80s business-slutty, and in a dreadful way). Best if it's something relaxed with a bit of volume (but, still structured), as in the picture.

Count another in the no-wrap/pashmina camp (sorry ladies).

+1 statement or nude/metallic shoe, not black or red. If you don't have orthopaedic problems, the highest heels you could possibly wear would look great, especially if you go with a longer blazer.

Makeup - for me a more modern look means really not much at all. Maybe a touch of liner and good mascara (no clumps, no spiky ends; more of an emphasis on mid-lash volume and clean tips). Enough that you feel more sexy/heightened than costumed. Sexiest of all is juicy-looking skin - just as much concealer as is required; not too much powder (aim: to glow); bit of blush. Shiny hair furthers the whole glowing thing, too.

Personally, I'd wear minimal jewelry, maybe a cuff. That dress is all about your back and legs.
posted by nelljie at 8:01 PM on December 17, 2012

Black pumps with a red accent (bow) would be great. The dress is supposed to be over-the-top; wear it with coolness.

Just don't up the ante - I'd recommend you avoid elaborate jewelry, patterned hosen, and strappy heels. Peekaboos are the ticket, or pointed-toe pumps.
posted by IAmBroom at 9:52 AM on December 18, 2012

I see a white crystal cuff in your future, per nelljie's suggestion. (Get me one, too.)

The reason I recommend a pashmina instead of any kind of jacket, is because you can let it slip and slide seductively down over your bare skin. Mind you, I say this both as someone who broadly ignores trends, *and* is anticipating an effect from the Anna Karenina movie which may not have any impact.

Wraps and shawls are an important part of my personal look, I realize that they may look dated if not a distinct part of your personal style already, but I do think the slipping-off-a-shoulder effect is worth it in your case.
posted by tel3path at 11:11 AM on December 18, 2012 [1 favorite]