I don't know how to dress myself. Please help.
November 16, 2016 12:24 PM   Subscribe

I need help figuring out how to dress for the theater in the winter.

I am FINALLY going to see Hamilton in Chicago in a couple of weeks, and I couldn't be more excited! My theater companions have also made dinner reservations at somewhere I believe would be considered "schmancy". But the problem is I don't know how to dress myself. I live in a much warmer part of the country, and I don't have "winter fancy-wear". So what the hell do I wear? I pretty much suck when it comes to personal style. I don't think I own anything appropriate, so I am willing to shop, but I also don't want to buy anything that I am never going to wear again. I am having an especially hard time imagining my legs and feet. Do I wear pantyhose? What kind of boots/shoes would I wear?
I work from home, so I don't have much of a wardrobe, and I get easily overwhelmed by clothing and fashion. Can you please help? Pictures and blogs with tips would be a huge bonus. Thanks metafilter, you're like the big sister I never had.
posted by msali to Clothing, Beauty, & Fashion (18 answers total) 4 users marked this as a favorite
I live in a much warmer part of the country... I also don't want to buy anything that I am never going to wear again.

Layers are your friend! You can wear multiple thinner things to replicate a heavy coat and shed them as temperature demands. I'd recommend fleece-lined tights and a little black dress. If you're a trousers kind of gal, regular officewear slacks and a nice top. Wear or at least pack a base layer, like HEATTECH from Uniqlo, for your torso. Add ankle booties or taller with a slight heel, a thick cardigan, and some kind of trench coat. Top with hat, gloves, and scarf, and you'll be good to go. If you're going to be doing schmancy things, expect that you'll be able to take a cab to get around rather than trudge through eight feet of snow.
posted by theraflu at 12:30 PM on November 16, 2016 [4 favorites]

Chicago's not so fancy that you really need to worry about this.

Seriously, I go to the opera wearing what I wore to work, and work ain't fancy either.

Find an outfit you feel comfortable in that YOU feel good in, then get yourself tidy. This is a time for your "nice" coat, not a big bulky parka, if you have that option, but really--we're a pretty casual city.

My standard being cute in the winter outfit is fun casual dress over black (or coordinating color) tights/leggings with a coordinating cardigan (or button up oxford underneath the dress, or both, depending on weather) and whatever shoes I'm currently feeling (nothing fancier than a pair of creepers, I guarantee you), with my pea coat, a scarf, and an extremely practical wool hat. I never feel like I look out of place.
posted by phunniemee at 12:46 PM on November 16, 2016 [8 favorites]

I don't wear dresses or skirts, so if I was feeling like I wanted to dress-up a bit, I'd dress the way that I do for a fancy cocktail party: fancy trousers, fancier (closed toe) shoes or boots, an evening blouse, some bold jewelry, and evening makeup. I'd also avail myself of coat check to store coat, scarf, gloves. You could also wear a hat, but I'd leave that as a last-minute decision based on weather. You won't be outdoors for long, so wearing heavy clothing that can't easily be removed is a recipe for being an overheated, sweaty mess. I'd probably end up looking like some variation of this. Remember that Hamilton is hipper than a formal opening night of the opera or similar. You can wear things that are far less conservative. Have fun!
posted by quince at 12:51 PM on November 16, 2016

I say this with an incredibly heavy heart, but there are very few places left where people will not wear jeans and sneakers. Even the theater (even the opera!). Even a schmancy restaurant.

However, fancy-people's loss is your gain! If you are wearing a skirt, wear tights (for warmth) and whatever shoes you normally wear. If you normally wear pants, wear one of your nicest pairs and whatever shoes you normally wear with them - business wear is acceptable. With pants, your socks should match the shoes (or be a crazy enough contrast that it looks intentional). If you have no cold-weather wear, get yourself a nice blazer you like that can work with your chosen skirt or pants, or a wool turtleneck sweater, which goes with pretty much everything. Since it sounds like you want to dress fancy, I would do it with accessories - some noticeable jewelry, for example.

If you are looking for shopping examples, pretty much every non-t-shirt-or-denim outfit on Modcloth or on Talbot's will work.
posted by Mchelly at 12:52 PM on November 16, 2016 [1 favorite]

Seconding the entirety of phunniemee's comment. That is definitely the Chicago Winter Uniform, and you can go with fleece-lined tights depending on how arctic the temperatures are.
posted by capricorn at 1:25 PM on November 16, 2016 [1 favorite]

When are you going, and what is your cold tolerance? We're seeing Hamilton in Chicago next week, and temps are looking to be in the upper 40s.

Also, are you driving or taking the train? If driving, how close are you parking?

(My plan was originally sweater dress and tights, but now I'm thinking that will be too warm...but I'm from Buffalo, so my cold tolerance is weird.)
posted by okayokayigive at 2:08 PM on November 16, 2016 [1 favorite]

I have been very happy lately in black leggings under a black knit skirt - both just above and just below knee lengths work. Top with a nice sweater, and put awesome boots on the feet, I've done a slouchy leather and a knee high successfully with both skirt lengths. Jewelry or scarf can increase schmancy-ness. For skirt, try jjill because their quality translates well to looking dressy despite being comfy. Leggings, Old Navy are great for the price, but I find JCPenney's to be more comfortable. Frye's Veronica Slouch boot (short or regular) is perfect with the look, but are pricey. I hope you have an awesome time at the theater! Don't worry too much about what you're wearing, you'll see a full range from the other people there.
posted by AliceBlue at 2:19 PM on November 16, 2016 [1 favorite]

Don't panic.

Number one: people go to the theater to see the show, not you. You do not want to distract the performers with wacky attire. You want something dark and plain.

In short, you want a little black dress. And you want it warm. And you want it fitted (no showing up to a restaurant in a snuggie, please).

So you want this. I know it's made of acrylic (ugh) but it has the right shape, the right length, the right neckline, and it has sleeves. It's fitted. You can wear it again.

Maybe you can find a similar style with some natural fibres thrown in, that would be good. But for now, let's assume arguendo that that is the dress you're wearing.

Now you don't want to be boring with your footwear, do you? No. You want these boots, which are under $100, per the reviews are extremely comfortable and walkable, and importantly for evening are not leather but suede-effect, and for walking/rainproofing are not suede but synthetic. With a patent looking trim. You can also get them in white for that space age look. Red or white.

Now you get these >70 denier Falke tights in burgundy, and you buy some black dye and turn them into ombre tights according to the instructions on this page.


Here is your velvet military frock coat from Zara. Hopefully it will be just slightly longer than the dress, but if not, it's OK because both are black. They suggest a beaded bucket bag at the bottom of that page; get that too.

As the first reply suggested, pack Heattech from Uniqlo as a base layer.

Most importantly, your underwear should be solid and smooth. Get this Jockey bralette in black. Your panties must be black and seam free.

Now get some spectacular earrings, perhaps red to connect the dots with your shoes. They should be simple in shape rather than fussy. They should be as large as you can get them without overwhelming your facial features, but no larger. This is what I'm picturing, or perhaps this (a bit too plain), but not this.

Finally, you need a cuff bracelet in red, white or silver; but since your features seem delicate, the bracelet should not be solid and chunky. Instead it should be like this or perhaps full of detail like this (not this, though, somehow...) Here's a whole page of black bracelets, I'm sure you can find something you like for cheep. Just don't get a bracelet that rattles, that's annoying.

Take off your watch; watches are not worn in the evening.

Get the plainest possible black knit hat, though I do think this one is cute if you want to spend the money and/or search for a cheaper version. If your hat is not black, it must be white or red.

Your gloves should be black and plain. I prefer fingerless gloves because I use my fingers almost every day, and gloves with fingers on 'em might as well be boxing gloves. But YMMV. Ask your hosts about their opinions of fingerless gloves. It doesn't look to be getting THAT cold in Chicago right now so I think fingerless is OK.
posted by tel3path at 2:30 PM on November 16, 2016 [14 favorites]

I am a huge proponent of dressing to the nines for special occasions (or at least erring on the side of slightly overdressed) but honestly, nobody really dresses up for anything anymore.

Assuming the theater in Chicago is comparable to the symphony in Boston, the average level of dressed-up is going to be business casual fading into jeans and hoodies, with a few people looking uncomfortable in dresses/jackets and ties they only wear a couple of times a year. Even if you only go for 'a little bit dressy' you'll probably be more dressed up than the majority of people there!
posted by usonian at 3:30 PM on November 16, 2016 [1 favorite]

Having been to Hamilton at the Private Bank theatre, I would not suggest wearing Heattech or any long underwear under your clothes. It was not cool in that theatre. If you fear being chilled, bring a pashmina-like wrap that you can drape around yourself or cover your legs with like a blanket.

I can confirm that unless it's a gala, most people in Chicago barely reach business casual or church clothes at the theatre. Personally, I always dress up cause I have the clothes and like to wear them. But something clean, in good repair, and that you feel good in is the right choice,
posted by crush-onastick at 3:41 PM on November 16, 2016 [2 favorites]

I'm going to Hamilton in Chicago in a few weeks. (I also live here.) I will be wearing...exactly what everyone else said. A knit dress, opaque tights, boots. What I wear all the days. Chicago doesn't really do schmancy. tbh if my social circle is any indication, you're more likely to see people in straight-up Hamilton costumes than a nice dress.
posted by goodbyewaffles at 3:57 PM on November 16, 2016

This is the scenario sweater tights were invented for.

Nthing business casual or "church clothes" for theatre nowadays. If even. I've seen plenty of people at the theatre in both New York and Los Angeles in jeans and t-shirts. As long as you don't dress like you're going to the gym, you're probably fine.

I'd be more concerned about the restaurant dress code, but even there, as long as you don't wear anything explicitly over-casual like ripped up jeans, a t-shirt with swears printed on it, flip flops, etc. it's probably fine. If it's a "jackets required" sort of place, I'd wear a dress, tights, and boots, probably topped with a cardigan or wrap.
posted by Sara C. at 5:27 PM on November 16, 2016

If there's snow on the ground, you want boots with a tread and if it's under 32f including windchill a warm coat that covers your butt. I saw Miss Saigon there about 20 years ago( most likely in chinos and a knit top), IIRC was able to put my coat in my seat.
posted by brujita at 6:15 PM on November 16, 2016

I do this every year in Ottawa. My secret, my great and foolproof secret, is budgeting for underground parking. Hopefully the theatre has it? Quick Uber to and from the restaurant while your car stays warm?

(The only time I ever saw jeans at this particular Xmas ballet at this particular theatre -- Ottawa is conservatively dressed but not crazy-posh -- the wearer was in a wheelchair and I assumed comfort and ease of dressing was the priority there. I've never seen jeans and tees aside from that one-off. The kids are in froofy dresses -- their 18" dollies are in froofy dresses -- the men are in suits or at least ties, the women are 'business formal' or better, and most people have their wool "good coat" instead of a ski-friendly parka.)

Also, old-lady-style pointelle underwear and/or slips that are thin and fitted enough to not make your dress lumpy are a huge help. I have some granny pants like this that go down about 4" and they make a huge difference, warmth-wise. (They have a matching tank top, too. First prize for sexiest lingerie of 100 years ago, I say.)
posted by kmennie at 8:04 PM on November 16, 2016

Yeah just a heads-up, we're having like the warmest November EVER in Chicago right now. It's gonna be 70 tomorrow. Seventy. You will NOT NOT NOT need heattech layers for a theater experience in two weeks.

Chicago does not care if you wear a watch after 5 pm. Chicago honestly DNGAF about *anything*.

When I went to the theater in Chi last winter I wore this but in gray, with black tights and black ankle boots. I was soooooooo overdressed.
posted by We put our faith in Blast Hardcheese at 8:53 PM on November 16, 2016

I see a lot of movies and plays, and fly in chilly planes, and in all these environments, sitting still makes my feet FREEZE. My solution: always wear long pants and long sleeves, and bring wool socks in your bag. When you get cold, slip off your shoes and socks and put on the nice dry warm wool socks. Also, bring a giant scarf and wear it as a blanket. Be practical and be comfortable! Life is too short to shiver during a long-awaited show.
posted by pseudostrabismus at 10:00 PM on November 16, 2016

Adding to the chorus, as a Chicago theatre-goer and sometime schmancy restaurant diner - office/church clothes - something just slightly nicer will do you just fine. Big venues (like Hamilton) will tend to be warm with all the bodies, so Heat Tech and the like, not necessary. Dark dress/skirt + tights and boots/booties and you'll blend right in.
posted by sarajane at 4:21 AM on November 17, 2016

Thank you all so much for your help! You have managed to calm me down. Tel3path, your answer is amazing (you are all amazing, her answer is just a little more amazing).

I wish I could take you all shopping with me!
posted by msali at 8:49 AM on November 17, 2016

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