Beauty Q&A: Freeboobing and Cute Pajamas

Will you talk more about freeboobing? Is it just an under-30 thing? Because I’ve had two children and my breasts have gone from a C (originally), to massive, to a less than perky A. Is it too late for me, unless I fork over the $7K and get my boobies reworked? It would be nice to look all fresh and hot, but I just don’t think I can pull it off.

Here’s my philosophy: only freeboob for a reason — to create a certain silhouette, because straps would ruin the look, because you’re trying to get laid, etc. Never freeboob out of laziness — you can leave that to the 23-year-olds. When you try on clothes that might work without a bra, look in the mirror and think, “but would I feel better about this if I were Bianca Jagger?” or some version of that. It’s less about having the exact right kind of boobs (no such thing) than it is a matter of putting yourself in the mindset of the woman you see rocking this look who obviously does not give a shit what anyone thinks, you know?

As for what to wear exactly, if you’re not feeling 100% awesome about your tits for some insane reason, try an open back sweater — the item I most often wear without a bra. You could also do a sheer top with strategically placed pockets or a drapey t-shirt with a scarf or cardigan for a little more coverage. But if you are feeling daring and confident, I personally think few things are sexier than all but Big Ang’s brand of boobs under a sheer-ish top. (Sorry, ladies with huge-mongous knockers. You get to have the kinds of fun most of us only dream of, so let us have this one stupid little thing.)

If you’re more into the shape that going braless gives you than the exposure, don’t forget about camisoles. Silk camisoles. Camisoles that will lightly lay over your boobs and disguise your nips, but still leave you with a silhouette perfect for draping.

And finally, you know what? I have nothing against plastic surgery. If you want your OG boobs back, you can afford them, and you’re willing to take the risks elective surgery presents, by all means.

Take-away: freeboobing takes planning and thoughtfulness, unless you’re Kate Moss.

Cute and warm shoes for winter: do they exist? I can’t for the life of me figure out what kind of shoes people wear in the colder months other than boots. I mean, boots are great, but I have a lot of wide-leg trousers that I wear to work. I feel like I can’t wear flats or heels in the office unless I trudge to work in fur-lined boots and change out of them when I arrive. Am I overlooking some huge shoe-genre? Am I just scarred by visions of clogs and chunky-soled beasts? What are some cute and warm footwear options for winter?

You ARE overlooking a huge shoe genre, and you’re right to do so. Sorry Merrell lovers (a.k.a “Mom”), but heavy-soled waterproof clogs are not a compromise in the interest of fashion.

You already have your answer, my dear, and that is to wear your comfy, cozy, sturdy winter boots to work and change once you get there. That is the price you pay for living in a seasonal climate, in addition to the price of having to suffer through snow and cold. (Very pricey!) It’s only for a few months, though, right? Carry a bigger handbag that you can cram a pair of shoes into until spring arrives. Do you have a desk? Desks are for hiding shoes under, mostly. Shoes and space heaters.

For fashionable versions of boots, though, allow yourself one pair of sexy but warm ones like these for when you want to look like a snow bunny. Or, if you can scrape $300 together, get a pair of Muk Luks, the boots UGGs aspire to be.

I’ve never liked cutesy, snug sleepwear. My standard sleep outfit is loose PJ pants and a big t-shirt. If I’m feeling wild, I’ll ditch the pants. That’s what makes me comfortable (it’s for sleeping, after all! shouldn’t I be comfortable?!), and that’s what I take with me when I stay over with my boyfriend. Cue his silent but palpable disappointment with the fact that I dress for romantic sleepovers the exact same way I would have dressed for a middle school sleepover.

Of course I’ve thought about trying out some sexy-ish sleepwear, but the few items I’ve bought, I found clingy and impossible to actually SLEEP in after the fun events prompted by the sexy outfit have commenced and it’s time to go to bed for real. I have a swingy little nightgown that rides up to my chest/neck in the night, leaving me strangled and otherwise naked. Many things with spaghetti straps get pulled and twisted and cut into my shoulders. And I really dislike any snug fabric around my tummy in general… that’s why I wear big t-shirts instead of cute little fitted tanks.

Do you have any ideas for some girly nighttime items that I can actually sleep in?

I do have some ideas, but first: it sounds like you hate everything! Stop doing that. How many times have you tried sleeping either naked or with one of these terrible, murderous sexy chemises on? Just like getting used to, say, living with a mild snorer, these things are usually only bothersome at first. If you try it enough times, I bet you’ll be able to fall asleep without thinking about what is or isn’t riding up where in a few weeks. I’m not advocating making yourself terribly uncomfortable or actually losing sleep, more what I’m saying is instead of listing in your head all the stuff you hate and won’t do, think of yourself as a flexible, ever-changing, open-to-new-ways-of-doing-things kind of person. This will be good practice for when you have to change something actually significant about yourself, which, if you’re in a committed, long-term relationship, is inevitable. (STOP EATING A MEAL AT 4 P.M. BECAUSE IT SCREWS UP MY DINNER PLANS WITH YOU EVERY SINGLE NIGHT.) Remember not liking sauerkraut? That’s what I mean. Now you LOVE sauerkraut and it totally gets you laid and snuggles you and makes your boobs extra fun to check out while you brush your teeth in the morning and you can hardly remember what life was like before awesome sauerkraut, right?

If you’d rather just have an answer to your question, get ready to spend a little money. I know investing in sleepwear is a toughy because hardly anyone sees it and you’re not awake to really enjoy it, but I find that the arbitrary price cap a lot of us put on spending in this area is a mistake. If you were to look at it another way, that you spend almost the same amount of time in these items as you do in your jeans, and that having a few sets on hand is a good idea since you also sweat in them and stuff, you may start to see the value in having a decent sleepwear wardrobe. Decide to invest a little and try to build a collection that’s a mix of high-end beautiful pieces and wearable but not disgusting ones.

Anthropologie has a whole department of adorable, sexy, and wearable bedtime items. Victoria’s Secret, believe it or not, has many affordable versions of what you’re looking for: something loose and cute that’s not a Mickey Mouse t-shirt and smiley face boxers. And if you start saving now, maybe you can have the world’s swankiest, comfiest PJ’s by retirement?

I am having a crisis of confidence regarding heels. I love shoes, and heels especially, but outside of very special events I can’t convince myself to wear them. I feel like I look like I’m playing dress-up. (I am 20 and a college student, so ostensibly I should be able to pull them off by now, right?) It’s not like I’m trying to wear any insane sparkly stilettos to class or anything, just maybe some appropriate suede booties, but whenever I try to leave my apartment I suddenly feel absolutely ridiculous and replace the shoes with like my duck boots so I can camouflage myself. It’s not like a ton of people wear them on my sort of remote campus but it isn’t WEIRD right? How do I convince myself wearing heels doesn’t make me look like an idiot? Also, part two of this question is how do I walk in heels without looking like an idiot?

I’m having a crisis of confidence regarding what to tell you. On the one hand, it sounds like you really want to wear heels all the time, and I LOVE heels all the time, and you should definitely be doing that if you want to. It’s pretty much the best, and no, heels aren’t “weird.”

On the other hand, then you went and told me you were an undergraduate student who isn’t quite sure how to walk in heels, and, get ready to hate me, but I’m gonna have to be the one to say it: there are few things more laughable and infuriating than watching a 20-year-old hobble around a college campus in shoes she doesn’t know how to walk in. Now are you ready for my mind-blowing advice?

BUY ALL THE HEELS AND GET ALL THE PRACTICE YOU CAN WHILE NO ONE CARES. Literally, you are in the one place on Earth where you are completely protected from most of your own image-finding mistakes. No one will shove you in a locker like they might in high school because there are no lockers and no one will put your photo on a blog and make fun of you like they will once you start going to the clubs when you’re 21. Practice every day. I promise you will look fine, and more importantly, feel comfortable in short order. Here’s my little “how to walk in heels” tutorial. Just think … in a matter of months you will be a fierce, high-strutting 21-year-old pump-wearing force to be reckoned with, and you’ll no longer care what anyone thinks about what’s on your feet because you will literally be above that. Like 4 1/2″ above that.

Orrr, never ever ever wear heels ever. I’m still going to, though.

Previously: Sex Hair, Fur, and the Perfect T-Shirt.

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