dressing for success??

imagesEvery industry, every event and every occasion used to have a quasi-rule book about what you are supposed to wear.  The world has gone casual.

When I was in my 20’s my Grandmother made me dress up to go to the bank with her.  It wasn’t like she lived in a city.  She lived in Laguna Beach which in the 80’s could not have been more chill.  Yet that was the world she came from.  Today I can go to the bank although now there are ATM machines in my sweat pants and nobody would blink.
I was living in LA when I’d go hang with my Grandma in Laguna.  I didn’t know about the dressed down look in LA yet.  I went to work everyday and had my work look.  One of the first Saturdays that I arrived I had brunch with one of my Mom’s dearest friends who we called Aunt Lolly.  I dressed up in my Saturday best.  My “aunt” showed up for brunch wearing a purple velour sweat suit.  It was a total aha moment about dressing for success.
Fast forward we enter the world of serious casual.  Heads of companies dress up hoodies and shlumpy jeans.  People in the tech industry are incredibly casual. It appears to be bleeding into other industries too.  I have very mixed feelings about the super casual look for all events.  Even the President doesn’t wear a tie all the time anymore.  It is a reflection of our times.
There was once a saying that clothes make the man/woman.  Maybe I am old fashioned but I kind of still believe in the importance of dressing for the part.  I am going to share one of my favorite things my Grandmother used to say.  Better overdressed than underdressed.  I think she knew what she was talking about.

Comments (Archived):

  1. Heidi Ehlers / HEIDI CONSULTS

    I wholeheartedly agree. Three years ago, on New Year’s Eve, my husband and I went to the theatre. We dressed as one would dress to a) go to the theatre, and then layer on that b) on New Year’s Eve. We were the only people who made an effort. Everyone else in car coats and winter boots and don’t get me started. It makes me sad.

    1. Gotham Gal

      I read this today. Quote by Miuccia Prada“What you wear is how you present yourself to the world, especially today when human contacts go so fast. Fashion is instant language.”

    2. Cam MacRae

      I had a fascinating discussion about this last time I was at the Met — long story short, the singers agreed that they preferred to see bums on seats.

  2. Lisa Abeyta

    Your post reminded me of the woman who taught my government class in high school. She was the closest thing to a hippie within the tiny Ohio community where I went to school, and she did not take it well when the principal informed her that she needed to dress more formal. For a week she showed up in sequined gowns. She ran the real risk of being reprimanded for insubordination, but in the end, the principal relented. I was a senior then, already managing a clothing boutique and wearing suits and heels to school because I often went straight to work. I think there is a balance between defining our own style while respecting the standards of the industry, culture or city where we are. And, yes, I agree with your grandma – it’s better to be overdressed than underdressed, because the latter can signal disrespect even when unintended.

    1. Erin

      Lol. I laughed at the sequined gowns thing.

      1. Gotham Gal

        Brilliant move

  3. Ella Dyer

    Your grandmother’s wisdom is timeless. Yes, better to be a bit more dressed as it also lends to the thought that respect is associated with how one dresses. It has been said that the women of Paris dress because they respect the city; I like that as I believe it also applies to how we feel about ourselves. One of my biggest observations is travelers who look like they just finished cleaning the garage. True, we shouldn’t judge a book by its cover but, the look doesn’t always lend itself to respect or, confidence.

  4. Matt Kruza

    I mainly favor more formal wear (minus ties.. I hate them!). But the bigger issue is just communicate expectations. Being massively over / under dressed can be both embarrassing personally and also insulting to everyone else there. This is an example of “use experience” in my opinion. When on a job interview you don’t tell the person what type of dress is expected, that is rude. When hosting a party / event/ convention, similar thing. That lack of communication on expectation and standards really bugs me and also leads to a lot of the problems, I think many people actually do / would like to dress up more but don’t want to be hopelessly overdressed. Communication people!

  5. WA


  6. Kirsten Lambertsen

    I think this is actually a really complex topic involving all kinds of things from (as you quoted) “instant language” to personal freedom to peer pressure to elitism to social rebellion and stereotypes. Fascinating and goes much deeper than whether or not a hoodie is appropriate.

    1. Gotham Gal


    2. Heidi Ehlers / HEIDI CONSULTS

      Great insight.

  7. pointsnfigures

    hahaha, we think alike. I have a bunch of Hermes ties I love and rarely wear them anymore. Have bow ties that I rarely wear anymore either. At the same time, I can’t stomach paying a lot of money for jeans so I buy Levi’s. A question that I cannot answer-if people dress nicer, does their attitude toward other people change?

    1. Susan Rubinsky

      FYI, you can buy all kinds of clothes at discount as TJ Maxx or Marshalls.Interesting question about people’s attitudes. I think attitudes go both ways. If you dress nicely, it makes you feel good and you spread that good feeling to the world around you. I guess there may be people who dress more formally because they feel they are better than other people but I don’t think that attitude comes from the clothes. Those people will be pretentious no matter what they are wearing.

      1. pointsnfigures

        TJ Maxx and Marshalls are good stops for some people. As @theGothamGal can attest to I don’t fit in typical sizes! Bad body type. Probably cheaper for me to fly to China and contract with people there to reboot my wardrobe! Size 14 A feet too. That sucks.

        1. Susan Rubinsky

          Ah, I get THAT. My son is 13 W in shoes. Damn near impossible for him to find shoes.

          1. pointsnfigures

            Yup. Allen Edmonds is a great source for dress shoes. They are the only ones I have until I can make a trip to Florence and get some made. That ain’t happening anytime soon. Is he done growing? Once you get to size 15 it’s almost impossible. I know of a store in Atlanta that caters only to big feet but haven’t been there.

          2. Susan Rubinsky

            I don’t know if he’s done growing. He’s 18. I suspect he may grow more. His Dad grew five inches between the age of 19 and 20. There are very tall people on both sides of the family. My son is only 6′ but all his cousins — both boys and girls — are taller than him, topping out at a boy cousin who is 6’7″ and a girl cousin that is 6’3″. His boy cousin has to special order shoes; I think he’s size 17 – ?

          3. karen_e

            Indeed. The question I think we are asking ourselves is whether as city dwellers/workers/creatures we are dressing and styling ourselves in the context of the city or in the context of the world wide web. Miuccia Prada expects to get her image published every day. So perhaps do everyday people who attend fashion shows (and aspire to a Prada lifestyle) because Scott Shuman might be around. To borrow from Eliel Saarinen, Mark Zuckerberg might be quite consciously designing his look “by considering it in its next larger context.” What is the next larger context for the person who leads Facebook?

          4. Gotham Gal

            Great question

    2. LE

      Once you have purchased a nice suit the shitty stuff stands out like a sore thumb. (Agree?). Probably the same for women’s clothing as well. Under that theory if you are not going to wear clothing “up to quality” you might as well not even be in the game. I don’t think a bank branch manger in a shitty suit impresses anyone who has higher economic status. He might as well be comfortable in dungarees.That said ironically many people think bank branch manager is a great classy job, because they get to dress up in a $200 suit.

      1. pointsnfigures

        Bought 2 Oxxford suits, and 2 Oxxford sport coats. They are hand made in Chicago and I was incredibly indulgent in purchasing them. But, they are awesome, fit perfect and will never ever go out of style. Had one made in Singapore. I have some off the rack suits from Brooks Bros and there is no comparison. But, the price difference is significant. Last time I had shirts made was 2006 in Singapore. Still fit, and still are great.

        1. LE

          I have some off the rack suits from Brooks Bros and there is no comparison.I find it fascinating (in a business sense) how you can separate someone from their money with the correct narrative and if you educate them on quality factors as well as social proof. [1] There is no question that I can feel the emotional value you place in the quality of the merchandise.Appreciation like that is the key to so much marketing. [1] Reason my mother would never be able to understand why I would buy a particular car. It’s art to me.Did you ever notice how once you shop for something all the sudden everything about the object stands out whereas before you never noticed it? Never gave a thought to the breakfront that my mom had when we were growing up (or any of the furniture). But then when I had to buy some for my own house all the sudden “wham” wow you can fully wrap your head around it and it seems like art.[1] Social proof (and art appreciation) is the reason everyone loves chef’s stoves. Not because most of them actually need them to do cooking (although some do for sure).

  8. Susan Rubinsky

    I love your Grandma! Mine was the same. She was the rare woman who worked throughout her marriage, not because she had to but because she wanted to. I recall one outfit in particular: a hounds tooth straight skirt (length was just above the knees) and jacket from the 1960’s. The skirt fell apart but I still have the jacket which I wear on occasion.I don’t really care what the fashion trend of today is. I always wear dresses and jackets for work. Clothes that look good on my body. I work from home so could easily wear my jammies without anyone knowing but I like how it feels to dress nicely. I don’t understand why people don’t care about how they look or why they look sloppy. I refuse to participate. I am almost always the best dressed person in the room.My son also has inherited the sartorial streak. He wears bow ties to high school! If you look closely every item he wears is carefully selected, from socks to shoes to jacket. Kids at school used to make fun of him but he has slowly gained an unspoken respect from his peers.

  9. LizScott

    At my brother’s first start up he instituted “Formal Fridays” — the one day everyone was REQUIRED to wear business suits. HA.Joking aside – I think there is such unappreciated importance on the value of fitting in. It’s not so much being over or under dressed as it is feeling like you belong with your peers (or, those you hope to be your peers.) And, I think this is a learned skill. My mom grew up without much and went to a school in a wealthy district; she never felt like she had the right clothes or the right look. She’s now in her late 60s and carries that feeling with her, all the time. As her daughter, I felt it, but in a positive way: she was mission-focused on making sure I had the “right” thing to wear so that I didn’t experience the outsider-ness she did. Didn’t matter if the thing was suit or a hoody; if it was a hoody, she was going to make sure it was best g-d hoody (and then she’d tell me to brush my hair, because fashion may come in go, but ladies, brush your hair, ffs)When I was in my 20s and starting out in management consulting, the firm I was at brought in a fashion consultant to work with the new hires — everything from “Oh honey, no, that hair color, no” to “this brand of suit/clothing will fit your body type well.” They knew the importance of your visual brand. Perhaps that way of working is a dying breed, but that doesn’t mean they were wrong.

    1. Kirsten Lambertsen

      I’m curious if the fashion consultant also advised the men?

      1. LizScott

        Yes! Interestingly, it was harder for the men to take in stride – I think perhaps they have less experience with people being outwardly critical of their physical appearance.

  10. Sherry Abdou

    My beautiful Turkish grandmother insisted on simple elegance when it came to fashion. Like your grandmother, mine felt one should always appear that they’ve given thought to their appearance before walking out the door. She would sport her best looks, with heels to the crowded dirt-street markets in Cairo. I may not select heels while getting groceries at Trader Joes, but looking ‘pulled together’ is important to me. My adult kids don’t necessarily agree; it’s a different generation. But, I’m hoping to see less PJ’s in public and hair that’s greeted by a brush:)

  11. Emil Sotirov

    Then, there’s the possibility that your Grandmother’s saying was about how to dress when you have to endure something like our Boston winter… 🙂

  12. LE

    When I was in my 20’s my Grandmother made me dress up to go to the bank with her. It wasn’t like she lived in a city.This dates from a time and a place where you could tell someone’s social status by the way that they dressed.I remember as a kid growing up two things. One was the poor warehouse workers (black) that worked for my dad always changed into nice clothes after work to go home. (They took the subway). The other is the cleaning lady (a white russian woman) wouldn’t let my mom drop her off in front of her house, she wanted to be dropped off down the streets so her neighbors wouldn’t see she that was a cleaning lady. (She also got redressed as well).Back in the day appearance mattered a great deal (I hypothesize) because what people thought mattered more than it does today. There was no social support system and no safety net. You had to behave and be in high opinion of your neighbors because one day you might need them.My parents are of an era where they never went in their own house without showering and getting “prepared”. My dad never ever wore a tee shirt, let alone a “wife beater”. My mom was always nicely done.She is in the process of selling our family house. She won’t let anyone in to see it unless it’s in pristine condition. No mess in that house when I was growing up.For sure, things are different now. But there is a reason for that.That said I am particularly proud about the fact that I landed my first big account (in the 80’s) at a hospital showing up in a down vest and dungarees. And I got the contract over Xerox professional salespeople, all spiffed up in suits. This was long before it was “fashionable” to dress as you wanted to.

  13. awaldstein

    The tip of a very big change.Beyond clothes.I used to do meetings on the golf course and smoke cigars back when, then dress up and go to dinner to do business.Lianna met with the CEO of a serious company in the wellness world awhile ago. They all went to an early spin class at Soul Cycle then went and grabbed a blend (hers of course) and talked business.As it should be.

  14. Sofia Papastamelos

    Look good, feel good, do good. I’m a big believer in that 🙂

  15. Brandon Burns

    I go to tech events in NYC and folks are usually dressed pretty well (comparatively). And even more so in media related companies, and the vendors that serve them. All mostly casual, as the times dictate, but with a sense of being put-together. Much, much more so that SF or LA.It really comes down to culture and taste. NYC is a culture of good taste. LA and SF, well… I’m not sure anyone would say the same thing about those cities.So, moral of the story, if you want people to dress better, keep investing in NYC companies so NYC becomes the dominant voice and resets the stage with a better look!

    1. awaldstein

      hmmmI spent most of yesterday at Soho House in meetings with entrepreneurs and a few investors.Style–dunno if I would say that. All over the place and interesting for certain though.

      1. Brandon Burns

        If not even Soho House could provide some decent looking folks, then we’re all lost!

  16. JLM

    .”Dress like the dummy.”I was getting out of the Army in the late 1970s and had really never worn civilian clothes. Four years at military school, five years in the Army. I was going to work in NYC for a big corporation.My mother, one of the wisest women in the history of mankind told me: “Dress like the dummy.”She directed me to Bond’s in NYC and told me that the “window dressers” who dressed the dummies were paid a lot of money to know fashion.She counseled me to buy the clothes the dummy was wearing because the window dressers knew exactly what they were doing. She was right, of course.When she would see me, she would say: “You look so handsome, just like a dummy.”Please do not tell anyone else this story. Just between us. Thanks.JLMwww.themusingsofthebigredca…

  17. ellen sing

    interesting because I just read an article titled”Luxury Marketers Beware: Drought May Be Coming” because people dress casually and having designer clothes and logo handbags are not a badge for success. They, of course, use Zuckerberg and his hoodie as an example for a successful person dressing down. I just think some people are slobs and never socially grow up. My husband, 40 years ago, dressed in a suit for business and now it is jeans and a golf shirt. Others in the company come to work in shorts and thongs. At some start ups, i have seen bare feet and those bare feet have no qualms about walking into the restroom.When I went to high school, I was suspended for a day because when I knelled down my skirt did not hit the floor. Those were the days of minis and no pants allowed. Two years later everything changed.There is nothing wrong with neat casual. I just hate dirty and sloppy.

    1. Gotham Gal

      When I was a kid girls were finally allowed to not wear jeans. Kind of crazy.

    2. Gotham Gal

      I mean to wear jeans.

      1. ellen

        We used to freeze in the northeast when we walked to school. Nowadays, it is more about the content and less about the clothes. Years ago my handbag had to match my shoes every time I went out. Too crazy. I was constantly moving important stuff around. Eventually, we put everything in a handbag dust bag and moved the dust bag from handbag to handbag. It was just stupid complicated.

  18. Darryl D.

    A relevant quote I recall hearing. Overdress if you’re getting paid (guest, employee…) and underdress if you’re paying the bill (employer/payer). The guideline is quite fitting, but I will typically err on the side of overdressing. I was raised to think it is a sign of respect to put the effort in to respect all others you deal with.

  19. KJP

    We were just discussing this at my law firm yesterday. We’re interviewing now and a woman showed up yesterday wearing a t-shirt with no bra under her unbuttoned cardigan. She was rather well endowed. This is a big downtown law firm and there is no way that would fly here even on ‘casual Fridays’. What was she thinking?

    1. Gotham Gal

      that is unbelievable.

  20. Yinka!

    Amen. Overdressed beats being underdressed. My approach is, if we must wear clothing, why not have fun with it? I don’t appreciate how the act of dressing up has become enemy territory in much of the west. In the same way that my senses would dulled if I had to eat the same meal or read the same book every day, it would be a sorrowful existence if I had to wear the same 1 outfit every day!

    1. Gotham Gal

      I totally agree. Boring!!

  21. Cynthia Schames

    Not only has the world gone casual, but it’s gone way downmarket, to the point where cheap imported “fast fashion” reigns supreme in every size & age range. Consumers bitch and moan about spending anything over $50 or $70 for a dress, but are shocked and appalled when it falls apart after 3-4 washes and wears. It’s called planned obsolescence, and our culture has bought into it hook, line and sinker. No wonder everyone looks a mess.I personally ascribe to the philosophy of “elegant casual” these days–even as I split my time between NY and SV. If I’m wearing jeans, they’re dark rinse bootcuts that fit well, and I’m far more likely to be wearing Manolos with them vs. flip flops. A few quality cashmere cardigans take the place of a hoodie, and I wear a MyTee most days (custom-made top from our line of American-made wardrobe essentials).We are getting ready to bring our software platform for custom apparel to select brands & retailers, so that we can start turning the tide of everyday dressing back to the days when fit and quality mattered.