Beauty Q&A: Dress Yourself in Pencil Skirts and Lingerie

I’m graduating from college in December and trying to get prepared for job/internship interviews. I pretty much dress like a college student — jeans, tank tops, dresses — and don’t even own any clothes that would be appropriate for an interview setting. What would you recommend, clothes and makeup-wise, for a look that is attractive and young, but also professional and composed? Also, I’m short, and I’m nervous that dress pants wouldn’t be such a flattering look for me. Any advice? Thanks so much!

When I first went out for real job interviews waaay back when I studied interior design at community college (I’m old, I keep trying to tell you), I thought you could only wear a skirt suit from Ann Taylor? So I bought one at the outlet. I didn’t get the jobs. Thank the lords that’s not what’s expected anymore! I know someone has convinced a few short chicks they can’t get away with them, but have you tried pencil skirts? They are THE quintessential “I will nail this fucking job so hard” item for every figure. Pencil skirts also transition well through all seasons with a little colored hosiery for winter or open toe heel in August. They look adorable with ballet flats almost anytime (during your morning commute, perhaps?). And, let’s be honest, they’re fucking hot.

Before you shop, remember: You are dressing for the job you want, not the one you have or whatever. That means this wardrobe update might cost you more than you want to spend in the short run, but it is a necessary investment in your future and you will make it back in no time.

So, starting with the skirt, my favorite place to look is Banana Republic. Seriously! I’ve had my black one from there for like five years. Put these in your closet: Skirt One and Skirt Two. Try tucking in any of these blouses (look for similar styles in rayon for cheaper) or channeling your inner Anna Karina and donning a bright sweater (check out the bit at 1:25. ANNA!). Pull the whole thing together with a pair of classic, sexy, undeniably grown up and sophisticated black pumps like these. Makeup-wise, subtle eyeshadow and liner plus glowy skin will get you overworked and underpaid in no time. I’m sorry.

It was so nice to meet you at the Hairpin meet up. While we talked briefly, you mentioned your outfit was from the Barney’s Warehouse sale, and I realized that that is a major question I have! How do I survive? And how do I walk away with awesome clothes?

Sample sales are a battlefield, and the best preparation is a clear mind, a good friend (if one is available), and the right undergarments. Real talk: You’re going to feel super icky and self-conscious and weirded out the whole time, pretty much, so stay focused on the task at hand, which is getting a DVF dress for under $100.

First, that clear mind: Decide the maximum amount you’re willing to spend on any given item and try to stick to that. Assess what your wardrobe is lacking before going in, and look primarily for those items — these sales are overwhelming, and if you don’t come in with a game plan you are going to get run over by the competition. Women be shoppin’. They will literally shove you and call you names. Don’t get shook. And whatever you do, DO NOT get sidetracked by a Lanvin gold lamé dress that has major butt cleavage just because it’s 90% off, making it a still-ridiculous $400. Unless that is exactly what you came in looking for. And lastly, try everything on. About that…

Most sample sales don’t have dressing rooms — at best you’ll get a communal room with mirrors like at Loehmann’s, so come wearing some nude-colored full coverage undies that will look OK under most anything and not leave you feeling too exposed in a pink thong and mismatched bra. (PS — You will see other people’s buttcracks and gross bras. Look away.) This one is good for the modest among us and this one is cheap and will look like an ugly bathing suit at worst. Bring a friend if you can because many sales have NO MIRRORS so you’ll need to rely solely on their opinion and how the garment feels on you. Second-best is asking a stranger to take a cellphone pic of you; offer to return the favor.

Finally, grab anything that seems like a remote possibility until you have about 20 items in hand, find a corner or empty-ish aisle, strip and start trying on as fast as you can. Head back out for round two. Repeat.

I will be getting married soon, and some folks are throwing me a lingerie shower. Which is super-fun! I am really very excited, as I love pretty things. So my question is not one of enthusiasm but of logistics. How … do people wear lingerie? I have two questions in particular. The first is: how to wear pretty bras under clothes? Without nipples showing? Do people just layer? Not care? I see these really sweet little bra-lets online all the time, but I just don’t get how they work. The second question has to do with more explicit getting it on/going to bed lingerie, like, let’s say, a negligee. Does one slip into the bathroom to disrobe/put it on before the Special Times? One must, right? How is this done in a non-awkward manner?

Congratulations! What fun.

To answer your last question first, you are correct! If you can’t wear the whole getup under whatever you wore to dinner, say this when you get home [Ed. — Wait. Wait. What is going on with that kiss?!]. Your partner will spend the minutes you take getting “comfortable” just SO SO SO amped they won’t even question it.

And about how to wear lingerie? I just go for it. Fuck it. (Outside of work, duh.) Remember back in the day when our moms didn’t even wear bras and it was like not a thing at all? And then remember Hollywood starlets constantly flashing a little lace or some see-through action? I feel like someone told young ladies today that they could only wear smooth polyester foam padded full coverage bras and there was no fun to be had in fancy underwear. Lies! All lies. Many of my favorite outfits have a particular bra integral to the look, and not a boring one either. I love a pop of color or pattern under a sheer dress or top, pretty asymmetrical accents on straps that show or even a bit of rhinestone or crystal glinting behind my blouse. Spouses in particular dig all of this. If you’re looking for a date-night outfit that will conceal your fancier underthings, check out Marciano (the actual store — their website sucks). They make affordable date dresses that are usually well structured with boning and enough lining to allow you to get away with garters and whatnot.

If you’re not sold on how much fun you should be having with this shit, allow me to recommend a bra and panty collection that’ll ease you into the idea that lingerie should not be an afterthought or something to go unseen:

Dearest Hairpin Readers,

Affordable. Sexy. Lacy. Sheer. Demi or Full Coverage. Completely smooth. Cleave-making. Boner-making. The Best. I present to you, the greatest everyday lingerie line of all time: Timpa Duet.


After 22 years in the sex industry (started at 19, still turning heads now at 41), I have quit to start a legit business. Now that I’ve retired, I realize how incredibly conservative and boring my wardrobe has become. I felt the need to look understated and invisible in my day to day life, to cover up the scandalous activities of my secret life. But I suddenly feel so free! And am remembering how much I once loved fashion. Loved dressing up, loved glamour, loved being daring with clothes. I’d like to have fun with fashion again, but I have questions.

1) A million years ago when I was young, there were certain immutable fashion rules. Like you can never wear navy with black. Or black with brown. (Obviously this wasn’t meant to apply to patterns, but more like, you can’t wear black shoes with a navy dress.) But now when looking at fashion blogs of the kids, i.e. Look Book, these rules seem to have been repealed? My mom and sister claim these laws are still in full effect. Who to trust?

2) There are ideas on these blogs that I would love to employ, but am not sure about the age appropriateness. People usually guess my age at least 10 years younger than I am, but even if I look 30, that’s a far cry from those youngsters. Example: high heel wedges with ankle straps and socks. Wanty! Now in my post-sex-work life I am the boss of me, so can dress however I choose. But I don’t want to stray into mutton-dressed-as-lamb pastures.

3) Any other sage thoughts to steer me in the right direction? That direction being away from turtlenecks and yawn?

I like you and I want to have brunch (read: mimosas) with you and go shopping.

1) A very well-dressed pal once told me, in response to similar worries, “Matching is boring.” It remains one of the most freeing ideas I’ve ever heard about fashion. Anyway, don’t be too restricted by these old rules — they are rules of thumb made so that people who don’t care that much about fashion can still look OK. People who, for example, would pair a long black skirt and a long sleeve knit brown top. Yuck. But! A brown pair of tight cords with black boots and black tank top? Hot. So I’m not worried about you. A few rules that should be heeded still? Linen only in the summer, wear white sparingly in the winter and don’t do too many crazy patterns at once. Another of my favorite fashion “truisms” come from What Not to Wear: Each outfit should have color, pattern, texture and shine. Think about those things more than these old rules and you’ll be aces.

2) You and me and everyone we know! Last year I literally cried on the train after a summer BBQ I wore booty shorts to because I realized it might be my last summer in them. Also I was drunk. Here’s my feeling: If you get that twinge of “Eek! If I saw me in this I’d be like ‘Hey, look at that old lady trying so hard to cling to her youth,’” go back to the drawing board. I tried the ankle socks and heels thing in my house once and it was basically as if I’d drawn a Sharpie on my laugh lines. NAGL. One big way you can tweak those younger styles is to add sweaters/scarves/leggings/tall boots to them to tone it down a bit. Look at the fashion blogs you’re into for fun, but then go study the mannequins on NET-A-PORTER for real grown-and-sexy inspiration. (And copy the looks with H&M/Goodwill finds!)

General no-nos for mom-aged folks:

– Mini-mini things, unless your legs are Tina Turner amazing. Even then, pair them with more demure tops and footwear.

– Low-rise anything.

– Avoid the Junior’s department. (Excluding basics for you petite things.)

– Uggs.

– Midriffs.

– Anything that evokes “little girl” or “doll.”

3) Enjoy your new found fashion freedom! Create a lookbook of your own with clippings from magazines of outfits you dig and bring it with when you shop. Wear denim that’s in style (excluding low-rise!) for as long as you shall live. Bold accessories and bright pops of color only get better with age. Try to avoid Eileen Fisher until you or your homies have grandchildren (if ever). Don’t stop caring about feeling and looking your best. And when you really start to worry about what your fashion future might hold, these amazing women will make it all better. Oh my god, I cannot waaaiiit.

Previously: Plane Face, Glasses, and the Home Pedicure.

Jane Feltes produces the radio program “This American Life,” and no one pays her to say any of this. Do you have a question for Jane?