How do you deal with back-handed “compliments” in the office? Reader B wonders…

I am a 30 year old lawyer working in Washington, DC. My late 20’s/early 30’s professional female friends and I have experienced a strange and disconcerting dynamic amongst women in the workplace: getting negative comments from other women for being smartly/well- dressed. These outfits, I believe, would objectively be considered professional, age-appropriate, and well-fitting: tailored suits in feminine cuts, pencil skirts to the knee, or pumps with a modest heel. They would certainly be similar to those depicted on the Corporette website. The comments often take the form of backhanded compliments, such as, “That shirt makes you look soooooo thin.” They may also be cautionary, like “Wow, you had better be careful not to hurt yourself in those heels”. This feedback comes from women at a similar professional level and more senior employees. It most often comes from women whom are a generation older and seem to be, at times, more about our size and age than what we are wearing. It also seems to be more of an issue in government and non-profit environments, as we haven’t noticed it to be a problem in the private sector. How should we respond to this type of feedback? At what point should we give in to workplace pressure to dress in a more bland way versus continuing to wear clothing that makes us feel sophisticated and professional?

This issue comes up a lot, and as your friendly blogger I see both sides of it: the younger women wondering why these older women are giving them these back-handed compliments, and the older women asking me how in the world they tell someone they’re dressed wildly inappropriate for the office in a casual way. I’m curious to hear what readers think about this.

A few thoughts:

• I think you always have to interpret what they’re saying as constructive advice for how to dress for YOUR office. Remember, ladies, just because something is featured on Corporette or in another “wear it to work” source doesn’t mean it’s appropriate for YOUR office, because every office has its own peculiarities. These older women are — hopefully — trying to convey to you that something about your clothes is inappropriate for the office.  The flip side: just because they’re saying these things doesn’t mean that they’re right, either — they could be jealous, they could feel threatened by you, etc, etc. But every time I’ve been on the receiving end of these kinds of compliments (and trust me, I have) I’ve studied what I was wearing, studied my office, and tried to make an educated, objective decision whether to stop wearing whatever was so offensive. These would be my interpretations of some possible “compliments”:
  • “Don’t hurt yourself in those heels” = “You look like you’re having a problem walking in those shoes, which is inappropriate for the office.”
  • “Oooh, cute dress — do you have a date tonight?” = “You’re dressed for your date, not your job, which is inappropriate.”
  • “You look sooo thin in that shirt” = “Wow, that is tight! Should I really be able to count your ribs?”
  • “Gee, I never would have thought to wear a corset top with a suit!” = “Why are you wearing a corset top with your suit?”  (Pictured: Victoria’s Secret.)
• In the instant it’s said, this is your response: a cheerful “Thanks!,” possibly followed by a compliment about her outfit or, should you choose, a note about your own attire. “I was inspired by Boss X’s great outfit on Friday,” or “I feel like I could run a mile in these heels!” or something positive. I wouldn’t talk about it more than that unless you’re in a formal setting (HR office).
• Here are some guesses as for why this issue comes up in government and non-profit offices but not the private sector: a) there are probably more older women in general there since there is often a promise of a better work/life juggle in those environments, b) they tend to be smaller offices with their own “personalities,” and c) they probably don’t have a separate HR department or other formal ways of telling you that you’re dressed inappropriately.  But, like I said, those are just my guesses…

Readers, how do you deal with back-handed compliments? Also, I’m really curious — would you rather someone say directly “that dress seems a bit inappropriate for the office,” rather than paying you some false “compliment”? For those of you who have tried to tell someone that she was dressed inappropriately, how did you do it (and what was her response)?

Do you have to wear pantyhose in the summer? The pantyhose-at-the-office question comes up so often, but I don’t think we’ve addressed it in a while — and Reader N wonders…

I had a question about wearing pantyhose. I’m about to start my first internship in finance (a mid-sized hedge fund) this summer and I’m really confused as to what to wear. It’ll be in London, so I don’t know if that changes business formal guidelines. Anyway, I’m 20 years old and a southern girl, and I’ve never worn pantyhose in my life. Is it really necessary to wear pantyhose with a skirt suit, even in the middle of July? I’m tempted to just wear a pant suit the first day and see what everyone else is wearing, but then I’ve heard people say that pantsuits aren’t conservative enough and I should wear a skirtsuit the first day just in case.

Obviously, I have no idea what I’m doing. Oh dear.

Congratulations on your summer internship — it sounds excellent. There is a really big range in what’s acceptable at conservative offices, and so — for my $.02 — it’s always best to get started on the right foot, which is to say the safest foot. You don’t want people’s first impression of you to be of your clothes — you want it to be of your work, your accomplishments. So for the first day — probably even the first week — I would suggest wearing:

•  Skirt suits (at least for the first day)
•  Nude-for-you pantyhose (pictured above: Wolford ‘Fatal Lace 15′ Seamless Stockings, available at Nordstrom for $50)
• Closed toe shoes
•  Sleeves, if you’re not wearing a blazer

You may realize pretty quickly that your female bosses all wear skirts without hose, and after that point you have my go ahead to ball up your pantyhose and pack ‘em away until interview season. Similarly, after a few days of observation, you may feel confident in bringing out your peep-toes and your sleeveless dresses. But the point is that you have to know your office.

Now, if you do get stuck in a firm where you have to wear pantyhose all summer… there are a few things you can do to make the summer go more comfortably.

- If there’s a problem with your hose (they fall down, they run, they cling to your skirt), odds are that you just haven’t found a great pair of hose for you yet. Readers have sung the praises of everything from Jockey to Wolford, so you don’t necessarily have to spend a lot of money; you just have to find a great pair that works for you. Personally I’ve always been a fan of control tops (even when I didn’t need the control) because the hose stayed up better, but that’s me — Spanx even has a higher-waisted version to prevent rollover.

- If you constantly feel sweaty while wearing your hose, first switch to all cotton underwear. (A reader asked me once if you needed to wear underwear with hose, and my answer there is yes — I’m not an expert but going commando in hose sounds like a recipe for a yeast infection.) If that still doesn’t work, you may want to look into thigh-high hose — a lot of women prefer those, particularly in the summertime.

- You may want to review my older advice on how to care for your pantyhose (as well as how to put them on).

Readers, which are your favorite pantyhose brands? For those of you who wear it even on the hottest days, what is your advice for Reader N?

How do you use friends of friends in your job hunt — whether through LinkedIn, Facebook, or just real life?  There have been an number of questions about this lately, including Reader A, below… her friend may be starting work at a company with a great work environment and has offered to refer her for a position once she starts, but as Reader A says:

… after looking into the company a bit, I realized that company is co-owned by an acquaintance of mine’s, “Ann’s” father.  I went to Jr. high through college with his daughter, we were on HS newspaper together and had the same major in college and were buddies, but not close friends.  However, it’s been about 6 years since college and she moved across country so we’re pretty much just Facebook buddies.  I would really like to ask if she could give my resume to her father as it could be very helpful in securing a position there, but I don’t want to seem rude.  If she worked there, I’d simply pass it along to her, but is it inappropriate to ask her to give it to her dad?  Also, should I have a specific position in mind or be open to anything (which I am?  What’s the best way to ask her?  Please advise me how to go about this situation!

This is a great question, because you should definitely ask.  Sometimes a script can be helpful when approaching acquaintances with a favor of this magnitude, though, so here is what I would say:

Dear Ann — How are you?  It’s been so long; I hope all is well.  Your family name recently crossed my path while researching a company I’d love to work for — it turns out it’s your father’s company!  Do you think it would be possible for you to introduce me to your dad via email? I’d love to get his advice for the best way to get into Office X.

A lot has happened on my end of things since our newspaper and college days — I’m sure it has for you too. I took my major in __ and worked at ___, getting really interested in __ specialty.  On the personal side of things I have an apartment I love, an amazing cat, and I’ve recently started dating a great guy….  Are you still using Major __?  What’s up with you these days?  Would love to reconnect the next time you’re back in town…

So, to break it down, here’s my advice…

- Be very clear about what you want.  Remember, people are busy, so you shouldn’t bury the lead: you want an introduction to her father.  In fact, I’d even put that as the subject line to the email or FB message.

- Be as warm as possible. Just because you’re being clear about what you want doesn’t mean it has to be an arm’s length transaction. I’d also say that just because you weren’t best friends 10 years ago doesn’t mean you might not be great friends now — people grow, and I would honestly look at this as a possible “new” friend, particularly if you work in the same industry.  Briefly disclose a bit of your life — be positive without bragging, and share without giving TMI.  If you’ve noticed on her activity stream that she recently got married, or moved to a new city, congratulate her on it — tell her the dress was to die for, or offer up your favorite restaurant in that city.  Be honest, of course, and not stalkerish.  Good: “I seem to remember seeing wedding pictures on your activity stream a while back — congratulations, you looked so happy!”  Bad: “I remember from your update on June 3, 2010 that you thought ‘people should mind their own business [insert other moody and purposely vague FB post here].’ I hope you resolved whatever that was about!”

- Be generally brief so the recipient reads and decides the outcome immediately, instead of setting aside the email to read later.  A lot of this depends on the recipient’s attitude about these things, more than your wording of the letter.  Some people will think, “Cool, no problem, I’ll dash off a two-line email introducing you and him.”  Some people will immediately think “Wow, I’m so not comfortable doing that;” some of these people will tell you that and others will just not respond.  Either way, by being brief and clear in your letter, you get the response immediately — whereas writing a three paragraph salvo may just result in the person saying “wow, this is long, I’ll read this later,” and then forgetting about it entirely.  (For my $.02, if I got an email like this from a high school/college acquaintance, I’d be fine to dash off a two-line email introducing you to whomever, but I would probably make it clear in that email that Reader A isn’t my best friend, she’s just someone I know from college and high school.)

Ultimately, though, I think this is one of those things where the adage, “You miss 100% of the shots that you don’t take,” applies.  Make the call, write the email — if you miss, so what? It won’t hurt in your current job hunt, and if this person is already just an old acquaintance, it doesn’t sound like your relationship will be changed much.  (Pictured above: Basketball hoop, originally uploaded to Flickr by Steve A. Johnson.)

Readers, what is your approach for using second- and third-tier connections in your job search?  How do you ask for referrals?

I’ve written before about how I love to get up early because that’s my most productive time of the day — but I don’t think we’ve ever talked about how to optimize those productive hours to get the most stuff done. I have my own tricks; I’d love to hear what you guys use as well. (I usually can be focused enough without time management techniques during this time — but they can be super helpful during other times of the day. Pictured: Pomodoro Kitchen Timer for Action Logging, originally uploaded by AndyRobertsPhotos. )

1) Know what you want to do. I always find this time is best to focus on ONE THING, not a whole to-do list. I don’t even WRITE my to-do list until later in the day, to be honest. When I get up early, I do the one thing that I need/want to do, and nothing else.

2) Leave some work unfinished so you can start in the middle. Writers are often advised to finish their day in the middle of a sentence, instead of at the end, so the next day you can just pick up where you left off.

3) Know your direction: forward or backward? I usually want to use the time to push “forward” — write new words, organize my research or my thoughts in new ways — but sometimes I prefer to go “backwards” and review work I’ve already done, such as when I want to edit something closely.

4) Avoid time sucks. I don’t look at email until 9 AM, for example, and I save other things that easily expand into longer projects for later in the day, when my focus is already not at its best. For example, in my law days, I saved research until the afternoon when I could, preferring to use the mornings for organizing the research or writing — now I save things like RSS feeds, Twitter, and Pinterest for the afternoons or evenings when I can.  On days when I really need to focus, I avoid turning on my computer when I can, and work with pen and paper instead.

5) Protect your productive time. If you’re super productive in the morning, don’t let friends or colleagues schedule breakfast meetings. If your best time is the afternoon, keep chatty coworkers out of your office.

Readers, what are some of your top productive times? How do you make the most out of them?

Reader L wonders if she can ask her adjunct professor for help finding a job:

I have an etiquette question for you. I am a third year law student looking for a job after graduation, preferably at a small firm or a nonprofit. One of my classes is taught by an adjunct professor who practices in the field I want to work in. What is the etiquette behind approaching him to see if he knows people who might be hiring? Thanks for any advice.

I’m curious to hear what the readers say here. Here’s my take:

Can you ask him if he knows of any open positions? Absolutely; there’s nothing inappropriate about that question. But let me warn you… here’s how that conversation is going to go: “Do you know of anyone who’s hiring right now?” Adjunct professor, thinking briefly of any jobs he’s heard of that day or week: “Nope. Sorry!” He won’t be offended, but you’re not likely to get much out of the exchange.  (Pictured: Einstein’s blackboard, originally uploaded to Flickr by rich_w.)

So here’s what you actually want to do: network with your professor. You want him to think of you when he sees a job a month from now, or two months from now, or maybe even three years from now. You want him to tell you the lay of the land in that field: who are the big players? Who are the big clients? Where is it heading? What are his favorite niche publications? Which is his favorite conference? What are the “offshoot professions” (there’s probably already a term for this, but I’m going to make up my own term for it right now) — the roads that people take if they decide they want to use their knowledge and expertise, but don’t want to be Niche Lawyer? (For example, in media law people sometimes became agents; sometimes writers themselves. They also sometimes went to work for media insurance companies.) Particularly in a tight job market, you might need to expand your search to include the offshoot professions, with hopes that you’ll still gain helpful resume experience, and networking connections, that will eventually land you your dream job.

So ask him to lunch. Make friends with him — tell her the truth, that you admire him, would love to be in his shoes, and want his advice. Ask him how he got to where he is, and slowly start to work in some of the questions above. At the end of lunch, ask him who else you should talk to — my guess is he’ll be happy to give you at least one or two names of people he knows. Your goal should be to come away from lunch with your professor with at least three action steps for yourself: something new to read (preferably an email newsletter or something free and regular), contact information for someone else to ask to lunch, and a few new Google searches to run yourself on the players and other facts you learn about at the lunch. You may even have a job to apply to, or an upcoming conference to try to attend.

Now the part that may be hard: asking an older man to lunch. There is nothing wrong with asking him to a one-on-one lunch, and if you have the guts to do it, my hat is off to you. Personally, I didn’t have the guts — when I was in law school, taking a class from one of the top lawyers in my preferred field, I wound up asking my adjunct out to lunch along with another classmate, my roommate’s boyfriend at the time. (Brutal honesty here: I wasn’t threatened by my male classmate at all — my worst nightmare would have been if my lunch date became the Golden Boy at my expense.) More reading for you: The Careerist just talked about how men are very wary of networking with younger women. Joy.

Readers, what is your advice for Reader L?  Do you have any great experiences you can share where you turned an adjunct/student relationship into a long lasting relationship?

Update: As readers are pointing out, the best way to get on the adjunct’s radar is to do really well in the class.  You may also want to wait until after the semester is over before asking him out for lunch (although I honestly think I asked my adjunct out for lunch while the semester was still ongoing, perhaps because it was a small enough class that our final in-class exam was done with numbers instead of names or some other blind grading method).

Reader D has a unique question: what to wear in the field?  More specifically, to visit a factory (and ride in her client’s plane!)

I am going on a site visit to a factory near Seattle.  The visit includes riding in a small plane and then visiting a large factory so I will need to be casual, wear flat comfortable shoes, yet still look professional.  Any advice?  Although I am a senior associate I will be the sole representative for my client and want to make sure I come off as professional as possible.

Congratulations on the opportunity — it sounds fun (riding in a private plane is on my Bucket List) and like a good career opportunity. As far as fashion goes, I think my answer depends on one question: can you wear denim around your client? If so, I think a pair of dark (preferably black) jeggings, tucked into flat boots, topped with a button-front and blazer, and accessorized with your normal work jewelry, would probably be my best guess for an outfit. (Update:  There’s a lot of disagreement with me in the comments, which is fine, but just to be clear: when I say “jeggings” — I mean skinny  jeans that have a bit of extra Spandex in them to make them more comfortable, but are still primarily denim.  E.g., these, these, or these. Not these.)  Here’s my thinking:

- Factory = boots. While ballet flats and other flat shoes have many things to recommend them, on the off (off) (off) chance something falls on your foot, you should be as protected as possible. Also, I think if there’s any uncertain footing that requires delicate stepping (e.g., over pipes), you’ll want to be in shoes that you know will not fall off. Oh, another reason: if it’s at all muddy or dusty on the runway (or in the factory), you’ll want the dust to stick to your boots rather than your pants.

- Factory and small plane = pants. See above re: delicate stepping.  I think it’s also possible in the factory you could be walking on grating, or on metal stairways, with people walking or working below, such that you wouldn’t want to wear a skirt.  I could also see there being some awkward stairways to get up to the plane (although it’s entirely possible I’ve just watched Arrested Development too much).

- Factory and small plane = tight-fighting, non-voluminous clothing. You wouldn’t want to get a flowing cardigan or skirt caught on a piece of machinery, or (ack) in some part of the propeller.

- Professional = blazer, dark pants. I would suggest that you carry over the jewelry you normally wear with suits to this more casual outfit — if it’s pearls and diamonds, do it; if it’s a statement necklace that you always wear, do it. Part of this is for a continuous look: the client has seen you wearing the jewelry before, and even though you’re in a different type of outfit now you’re still, at the core, the professional lawyer he knows. Another part of this is to help YOU feel confident and be in your zone for your most professional self. For me, for example, that means putting on my good watch whenever I have a business meeting, no matter what I’m wearing… even if I don’t wear the watch when I’m lazing around the house or hanging out with friends.

So all of these thoughts, above, send me to jeggings, flat boots (get ‘em shined before you go!), a nice top, a blazer, and your work jewelry. There are some non-denim leggings that have enough weight to the fabric that they can be worn as pants (despite the popular Buzzfeed “am I wearing pants” flowchart) — I got a nice ponte pair from Ann Taylor earlier this year. If you really would rather wear proper trousers, I might still advise wearing flat, knee-high boots beneath them — that way if conditions are really horrible you can tuck your pants into your boots.

A few other considerations: plane and runway = wind, so I might suggest pulling your hair back from the get-go. Keep in mind, though, that the factory may require you to wear a hardhat, hairnet, and/or goggles… so I wouldn’t do anything too fancy that will interfere with those requirements.  In other words: low “on purpose” ponytail, not a French twist.

Readers, have you had to visit factories (or, speak up ladies, how many of you have ridden in private planes)? What would you wear?

As today is Administrative Assistant’s Day, I thought we’d have an open thread about what the best thing your secretary/assistant has ever done for you. We’ve talked about what you can delegate to assistants before — what DO you guys delegate? What do you look for in a great assistant?

For my own $.02, the best assistant I ever had was only mine for a short period — she was attached to a partner down the hall who had a niche practice, and when the partner moved offices, so did my secretary. But in addition to being pleasant and nice, she was really smart — I felt like I could give her anything and she would do a great job with it. I wish I could remember something specific she did that went above and beyond, but really she was just generally excellent!

(Pictured: Files, originally uploaded to Flickr by Velo Steve.)

Reader A asks a great question for everyone who had a wilder youth:  what to do about tattoos in the office?

As I’m now a law student, I’m worried about how to dress in order to hide my tattoos, which go from both shoulders down to right above my elbows; they’re dark enough to be seen through most lighter button-downs. Not that it matters, but they’re all very tasteful– I went to art school in my wild undergrad days. Now, though, I’m wondering whether I’ll be forever banned from wearing any sheer blouse or sleeveless shirt. Am I destined to wear collared shirts for the next thirty years of work? Any advice would be appreciated immensely.

We haven’t talked about tattoos in the workplace for years, so let’s revisit the subject. I will say at the outset that I think tattoo sleeves are in a very different category than the tiny tattoo somewhere noticeable (wrist, ankle) or the bigger tattoo somewhere generally hidden (lower back, shoulder blade).  As someone with tattoo sleeves (or half-sleeves) (tattoo ballet sleeves?), you should not only know your office, but I think should also know a) yourself, b) your boss, and c) your business relationships.  (Pictured: Shading, originally uploaded to Flickr by liquidnight.) Here’s what I mean:

In a conservative office with conservative clients, I’m sorry, but yes, your tattoos are likely something you’re going to hide, at least most of the time.  I would always hide them for interviews and first meetings, and honestly, for the first ten meetings.  Once you get to know someone (the boss, the assistant, the client, the opponent, whomever) you can show more personality, which can, in some circumstances, include showing your tats.  (You say they’re all “very tasteful,” so I’m assuming there’s nothing unsuitable for the office with your tattoos, such as nudity, foul language, etc.) In some jobs — where literally any day could be the first day you meet a new big client — this will effectively mean you have to cover your arms most of the time.  On the plus side, a blazer looks professional with so many outfits and will effectively hide your tattoos, so you should be fine; in many ways, your tattoos will be easier to hide than the small wrist or ankle tattoos that some women get.

That said, are you really the type of person who wants to work in a conservative office?  At least in my experience, the “I have tattoos from my shoulders to my elbows” person is far different from the “I got a butterfly on my ankle on Spring Break” person — it takes commitment (and I’m guessing a fair amount of pain) to get that much ink, and probably was not the result of one night of drinking –  but it also means that you probably dance to the beat of your own drummer and may have less respect for conventions and authority.  I’m going to guess that even if the work of a conservative office appealed to you (e.g., a big firm that has a great art law or entertainment law division), the atmosphere of the office would grate on your nerves after a year or two.

So I think your approach to jobs should be thus:  If you’re going for a conservative job, consent to covering your arms for most of the time, ideally with a blazer.  Especially with a large law firm, this can be a great first step because of the connections you make, the experience you get, and the doors that are open to you afterwards (to say nothing of the salary) — so covering your arms shouldn’t be that big of a tradeoff, at least for a little while.  When seeking a less conservative job, though, I would advise covering your arms for the interview — and then seriously gage the interviewer and office to see how good of a fit you, your tattoos, and your personality may be for the office.  If it’s really important to you, ask about personal expression, the dress code, what kind of client interactions, and more — because the fit of the office is going to be key to a happy work environment for you.

Readers, what are your thoughts on tattoos in the workplace?  Do you think some tattoos put people in a different category than others?  Has anyone had experience with tattoo removal on a large scale, or covering tattoos on a regular basis for work?

By the time I started working in BigLaw, I’d had about seven jobs before that.  For four of those jobs, my bosses were women; the other jobs (lifeguarding and two fashion magazines) were, well, not exactly testosterone-fueled environments.  Everyone had called me by my first name, and we generally enjoyed a collegial atmosphere.  However, when I started working at the law firm, I began to notice what felt like a very male-friendly environment.  Nothing was sexist, per se, but it still contrasted sharply with the work atmospheres I’d known before, and made me feel out of place.  (Pictured: Team jersey, originally uploaded to Flickr by nats.)

One of those things was being called by my last name. I’d always hated sports growing up (despite having, at various points, been a member of the tennis and swimming teams), and nothing annoyed me more than people saying “Let’s call Vogele” or “Whazzup, Vogele?” (As you may have guessed, my maiden name is Vogele.) What annoyed me even more about the last name thing was that it wasn’t men who were perpetuating it — it was women, who, I assumed, were trying to fit in with the old boys’ club.

At one point, in my first or second year, I was on a team of four female associates, led by another woman or two in charge of us — and yet we still all went by last names. One night, behind closed doors, I ranted to my good friend about it, going on and on about how much I hated it.  Was I supposed to catch a ball sometime soon, or go long?  (Alternately, where was my pipe, whiskey, and manservant?)

And she pointed out that two of the four of us had the same first name. Well…. FINE.

I’ve learned to live with being called by my last name only — but I’m curious what everyone else’s take on it is? Do you get called by your last name in your workplace? Does it seem like a part of the old boys’ club?  Are there other little things that grate on your nerves?

What kind of car should the overachieving chick drive?  On the one hand, a designer car could impress clients and colleagues… but on the other hand, it can also convey that you’re “not working for the money.”  Reader K wonders:

I’m graduating from law school next month and I’ll be starting at a large regional firm in the Fall. For the past 11 years, I’ve been driving an old 2-door Honda. It was a great car for commuting to law school, but I’m definitely ready for an upgrade. My husband and I have talked about buying a new car and he really wants a higher-end sedan (audi, lexus, acura). I would love a luxury car, but I would be equally happy with something more modest. I’m worried that if I pull up in an expensive new car on my first day at the firm, my colleagues will assume that 1. I don’t really need to work (untrue) or 2. I’m materialistic and fiscally irresponsible (also untrue). My husband and I are in our 30′s, we’ve both worked and saved for quite a few years, and I have a small amount of law school debt, so it’s within our reach to upgrade.

Am I worrying about nothing or should I consider my colleagues’ perception when deciding what type of car to purchase?

This should be a fun one — I’m already seeing shades of our engagement ring discussion, as well as our intern-with-the-Birkin discussion.  I should say upfront that I’ve been living and working in NYC for about 15 years now, and cars just don’t matter that much here. (Pictured: Devan’s Pimped-Out Ride 3, originally uploaded to Flickr by Jennerally.)

Financially speaking, I’ve always been taught that cars are depreciating assets, and so it is always a bad decision to lease them — you should strive to buy them outright (all cash) whenever possible, and keep the same car for as long as you can. (Although: apparently only 11% of people buy cars outright.) I will also say that of the many friends I have who drive luxury vehicles, the vast majority of them are making monthly payments on them or leasing them, and trade them in every few years to get newer, better cars.

So I think we’ve got a lot of competing judgments that people may make about you based on your car.  I think most will assume you’re making monthly payments on it or leasing it; some may think “Ooh, nice car, she can afford a monthly payment that high;” and others may think “Huh, she probably didn’t have the cash to buy a $20K car outright so she may as well get a flashy car if you’re making monthly payments,” and still others may think “Wow, she’s loaded!”

If the choice is between buying a lower-end car in cash, versus making payments on a higher-end car, you may want to consider the advice Men’s Health gave recently to its readers on how to attain status symbols: buy a slightly older car, like a 2003 BMW.  The cost may be low enough that you can buy it all cash, you still have a status symbol, and if people think anything of it, they may think “ah, she appreciates quality but also makes prudent financial decisions.”

For my $.02:  I think ultimately you should look at your family finances, weigh that against your desire for the car you like, and get the car that makes the most sense. Readers, given your druthers, would you rather own a brand new car outright, make monthly payments on a fancier car, or own an older, fancy car outright?  What judgments do you make about people based on their cars?