Posts Tagged: style

Reader Request: Balancing Style and Appropriateness

personal style dress code

Reader Maddie sent me this request:

Something I think a lot about is how to balance “dressing for situations that require ‘appropriateness'” vs “dressing in a way that makes me feel awesome and cool.” Like you I’ve been trending much more edgy – cool recently, and it’s a balancing act to figure out how far to let that go when I’m on site with a customer at a big health system. For example, I’m not taking out my eight ear piercings, no sir, but should I balance that out by not wearing my pointy edgy heeled booties? Is a leather pencil skirt too much now that my hair is dyed dark and I’m not pairing it with a cheerful floral, but a dark blouse? (But also, forgive my French, fuck the patriarchy, where does that fit in?) Are there some general ideas/guidelines for how to keep from accidentally going too far? I don’t care too much about offending people, but I do read the boss-lady blogs like Corporette and I really struggle to reconcile the dress-for-you vs dress-for-those-around-you-at-work messages I feel I get from different camps.

SUCH a tough one. And I will open this particular can of worms by saying that learning to balance your personal style preferences against the expectations of those around you is a delicate art, and also a highly individual one. What you can “get away with” depends on your environment, tasks, and – to some extent – personality. I can offer loose guidelines, but you should always trust your gut. And when your gut refuses to offer any guidance, consult your friendly HR rep. Or, if you feel comfortable, chat with your manager. I sincerely doubt anyone will dock points or giggle at you for asking earnest questions about what you can and cannot wear to work/with clients, but if they do? Better get that embarrassment and aggravation out of the way up front, and feel confident of your choices moving forward.

So. Here are some ideas to ponder if you aren’t sure how to balance what you want to wear with what you’re expected to wear:

One envelope-pushing item per outfit

As Maddie guessed, it’s gonna be easier to get away with a leather pencil skirt if you balance it out with something from another fashion family – something soft or retro or colorful. Something distinctly NOT tough, edgy, or sexy. Juxtaposition is your friend, and can help you slide a few items aligned with your personal style into outfits aligned with your boss’s expectations. (Or your friend group’s or your in-laws’ … this works in multiple settings.)

Accessories generally get a pass

If you’ve got a dress that you think is toeing the line, you’re probably better off relegating it to weekend wear. But aside from anything printed with obscenities or designed to be reminiscent of genitalia, most accessories are easier to incorporate into conservative, work, or client-facing outfits. OK, you might not want to wear a black leather dog collar or five-inch perspex heels … but chunky necklaces, funky shoes, stylized eyeglasses, unusual watches, and sculptural handbags will simply create interesting contrast against more conservative clothing.

More coverage = less kerfuffle

And here we delve into irritatingly patriarchy-related territory: Most people are more willing to accept unusual, edgy, or stylized pieces if they offer coverage rather than being revealing. Which is stupid and confining, but can also be used somewhat subversively. A skull-print top that’s sleeveless and low-cut will turn heads, but a skull-print scarf worn with a crew-neck and blazer might not even register. A leather miniskirt will cause a stir, but a leather miniskirt worn with opaque tights and knee-high boots could pass muster. If you’ve got something you know to be controversial, wear it in a mix that errs on the side of more coverage.

High quality, good fibers

Clothing that’s well made and created using high-quality fibers will generally make its wearer look sophisticated, even if it’s done up in wild shapes or funky prints. If what you’re wearing is both cheap and borderline-inappropriate, it’s more likely to attract attention. Which doesn’t mean you should start buying super-expensive clothes that might get you in trouble with your manager! Just know that you can get away with more envelope-pushing personal expression if you make sure to keep some top-quality items in the mix.

Very few of us are privileged enough to have total freedom when it comes to style choices, and it can feel stifling to conform to employer or social expectations. But there are always ways to make sure your unique style shines through, and I hope some of these will prove helpful to you. And to Maddie!

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Clothing Commentary

I’ve begun updating some of my greatest hits posts so they’re more current. This is one of them!


This is my Audra Jean underbust harness. (That link is prolly not quite safe for work viewing …) I’ve had it for years, worn it in a variety of ways, and loved it all the while. It’s funky, badass, the perfect piece for bringing in a floaty A-line dress like this one, and a pleasure to wear. It is also a piece that some say has a design influenced by BDSM, and although I respect the BDSM community it’s not my scene and not why I like this harness belt.*

And no one has ever said anything nasty about it. Not directly to me, anyway. And I’m able to field whatever questions and opinions get thrown at me, no problem, because I’ve had years of practice and given it loads of thought.

But many readers and friends have mentioned that they love the idea of dressing smartly and stylishly – or even edgily and unusually – but worry about how peers will react. Specifically how often peers may comment upon or question any noticeable changes in personal style. So I thought I’d offer up a few suggestions for dealing with clothing and style commentary from your peer group.

Mentally prepare

If you’ve gone barefaced for 15 years and suddenly start wearing full makeup every day, people will likely notice and comment. If you’ve worn jeans or pants for ages and start bringing skirts and dresses into the mix, you might get a few questions. One reason why these inquiries feel difficult to handle is that they surprise us. Just knowing that your changes may prompt a few curious questions can help you feel more prepared to react and respond.

Role play

If you’re very anxious about how you might handle potential comments and questions, have a friend or loved one do some role playing with you. You can probably imagine most of the stuff that’ll come at you: “I don’t think I’ve ever seen you in slacks, Jane!” “Wow, new hair. Big change.” “You look so different!” “So dressed up. Going for an interview, or something?” Jot them down, and do a quick dialogue. You’ll be amazed by how this exercise will prime your mental/emotional pump for the real deal.

Have short and long responses

Even if the role playing thing seems a bit too in-depth, consider mapping out some potential replies to questions and comments. Different questions require different levels of response. You needn’t launch into your personal style journey or the decision-making process that led you to switch from heels to flats or long hair to short. Not with everyone. “Wow, new hair. Big change,” can get a simple, “Yeah, it is. I’m loving it!” On the other hand, “So dressed up. Going for an interview, or something?” might necessitate a bit more background. Something like, “Nope, just felt like it was time to mix up my personal style a bit. I’m having such fun with these changes!” Judge for yourself who merits a quick reply and who needs a deeper explanation.**

Give it two weeks

This nugget comes from the ever-wise Husband Mike. Several years ago, he decided to wear suits to his SUPER casual office. Every day. He wanted to make it his personal uniform. And, as you might expect, he got a stream of “job interview” jokes and curious comments. But they lasted for two weeks, then tapered, then stopped completely. Now, this will only help you if you’ve made a relatively drastic change and plan to stick with it consistently from here on out. If you wear the occasional foofy tulle skirt but generally stick to pencils and A-lines, that’s a different deal. But if you get a makeover, switch styles drastically overnight, dye or cut your hair, or do something similarly permanent, count on about two weeks of inquiries. Your peer group should acclimate by then. (Hopefully.)

Stay positive

I try so hard to assume the best about everyone, but I do feel that this kind of question/comment behavior requires some guardedness. If a coworker points out that you’ve changed your appearance and you shrink back in dismay or alarm, you’ve revealed a chink in your armor. If instincts kick in, your coworker may start asking more questions, or teasing, or prodding for more information. You made these changes because you wanted to, because doing so boosted your self-confidence, because you want to look and feel fabulous. Make sure to say so! If a fellow student saunters up to you and says, “Whoa. Why on EARTH are you wearing high heels to class?” say, “Because they make me feel gorgeous!” If your aunt says, “I wish you hadn’t cut off all your beautiful hair,” respond with, “Well, I did. And I think this new ‘do suits me perfectly!”

Of course, if someone is being rude to you, butting into your business, and commenting on your body, appearance, weight, or anything about your physical self, you always have the option to tell them to butt out and eff off. Your body, your business, PERIOD. However, you may reclaim some of your power by acknowledging their observation, owning it, and putting your own positive spin on it. When a person offers a negative or teasing comment on your appearance, they are likely trying to get a rise out of you. It’s classic bullying. Swearing, silent treatments, and rants can feel awesome. Denying a bully the satisfaction of an outraged or hurt response can feel even better.

Clothing, grooming, and appearance-related commentary is such a mixed bag. Compliments are like tiny little blessings, and can inspire unexpected joy. Comments and questions can cut both ways, and might make us feel scrutinized, judged, or targeted. But I hope that the possibility of generating curious queries won’t keep you from tweaking, finessing, or even completely changing your style or appearance. With a little bit of knowledge and foresight, you can field those questions with grace and aplomb.

*Think this is unusual or dishonest? Consider how many people own motorcycle jackets but not motorcycles, or how many wear cowboy boots but have never been near a ranch. Lots of task-specific or community-specific pieces end up in the fashion mainstream, and since Taylor Swift is a fan of harnesses, who knows? They might be next!

**If anyone. You have no obligation to explain yourself to anyone at all. But in terms of diplomacy, it’s often more advantageous to offer truthful information than withhold everything and let people make their own assumptions.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

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Reader Request: Body-con Clothing for Older Women

tight clothes over 40

Reader Amy had this question:

I’d like to know more about how to find body-con clothing that is flattering and also doesn’t make it seem like I’m trying to look super young.

I’ve been getting lots of age-related questions lately! I love this one because, like another recent question about dark wash jeans and older women, it illustrates just how arbitrary our age-based style rules really are.

So let’s say you’re 26 and really happy with your body. If you wear body-skimming dresses and shorts no one will bat an eye. Or relatively few eyes will be batted anyway. If you’re 56 and really happy with your body, wearing body-skimming dresses and shorts will cause an alarming number of eyes to be batted. And why is that? What’s so appalling about seeing the thighs of a 56-year-old, or the outline of her figure under a slinky dress? Even if she conforms to the current beauty standard and is slim, toned, and hourglass-y some would still argue that she should wear looser dresses with more coverage and Bermudas or capris. And if she doesn’t, well, people love to police bodies and the policing of older bodies is practically a national past-time.

So, ya know, wear what makes you happy, no matter your age. Wear what makes you feel strong and vibrant and alive, no matter what other people may think or say. You’re the decider. Body-con in your 80s if it makes you feel like a million bucks.

Since Amy is asking specifically about doing body con without looking like she wishes she were a college co-ed again, I’ll offer a few tips. But, as always, none of my figure flattery advice posts should be considered gospel, including this one, and I fully expect you to read them with a grain of salt. Style “rules” are merely guidelines, no matter who is dispensing them. I trust you to use your judgment. And I trust you to take what applies to you, discard the rest, and assume positive intent. OK, now that we’re clear …

Watch your fabrics

Thin, drapey materials with any sort of a sheen will read as younger than thicker opaque ones. So a body-con sheath dress in slinky jersey might feel wrong, but the same dress in ponte knit might feel oh-so-right.

Consider your colors

Dark, dusty colors generally look more sophisticated than light, bright ones. If you want to make sure your body-con dress or top looks as chic and classy as possible, pick jewel tones or muted colors over primaries, neons, and even pastels.

Monitor exposure

I kinda hate to include this one since it’s so age-ist in a lot of ways, but if you’re looking for traditional advice here it is: Watch your necklines and hemlines since garments that are both body-con and revealing can read “mutton dressed as lamb.” A form-fitting sheath with a knee-length hem and relatively high, cleavage-covering scoop neckline may feel more appropriate than an above-the-knee frock with a plunge neckline.


And finally you can make slim-fitting garments look more grown-up by wearing them in layered mixes. A form-fitting top or dress can be just as flattering and fun under a nipped-waist jacket as it is worn alone.

Images courtesy Talbots

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

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