Privilege Blog

What To Wear On Your First Day Back At Work

Yesterday morning I woke up at 5:30am. When the time came to get dressed, I pulled on my clothes, put on my shoes, and looked in the mirror. “Hmm,” I thought, “These shoes are not quite the right height for these trousers.” Just before I left the house, I took this picture outside my front door. Upon reviewing it last night, I realized my pants are too big. Let’s regroup.

  • Clearly in the work world strategy takes precedence over appearance
  • We all know that business casual is the devil
  • I have learned that one can only truly optimize for one thing at a time, and work performance must come first

But have no fear, all is not lost in the land of style. We are not defeated by too-large pants, nor too-flat shoes. Nor, fortunately, does everything require a bullet point.

My primary Use Case for this outfit centered around Meeting People For The First Time, in a very informal environment. As Malcolm Gladwell wrote in Blink, people form pretty accurate opinions on small slivers of data. I’d worn everything here before except the shirt, and I felt exceedingly comfortable with the combined effect. Serious, classic, avoiding rigidity with help from a little trivia at the neckline.

Details? Banana Republic pants, a generic label black cashmere v-neck from Bloomingdale’s, black quilted Manolos, my Rolex, traditional small gold hoops, and two gold chains. Oh, and a new lavender gingham shirt from J. Crew. Back-to-school shopping, if you will. For some reason preparing for this job summoned a vision of purple gingham. Why I do not know. I have never worn such a color or pattern previously. But I have learned to obey wardrobe spirit guides.

Here’s a tip. If you look best in blue, wear purple tops with a pink lipstick and many things are put right.

I kept my glasses on for these photos to show you how I  really look, in the office. I wear reading glasses with regularity, and perch them on my head throughout the day when not in use. I believe I need a lighter pair. But I don’t want to get all crazy-like and wear colored spectacles. Heavens forbid.

And so it begins. In this post, from very early in Privilege’s history, when I misplaced my job originally, I wondered what a 52-year old woman might wear. Over the past 2.5 years I have sorted out an about-town style. The photo above is the Privilege starting point for business casual. Let’s see where this particular journey takes us.

61 Responses

  1. I bought that shirt at J.Crew on Sunday morning. I love it – not sure why either.
    Also bought 3 of their v-neck cashmere sweaters, black, navy, and gray. They’re great, a nice close, but not tight fit. And did you know their cashmere is made in the same place as Loro Piano’s?
    I think you look great in the photo, but yes, the pants are too big :) I also like your reading glasses in tortoise. I don’t think I’d go lighter, gives a nice edge.

  2. Congrats on the new job. And what a wonderful time of year to be starting. No matter the age, I always feel that the back-to-school crispness and brightness of fall heralds great things.

    I’ve been eyeing those J Crew shirts myself. One of my regretted non-purchases was a similar gingham shirt. I was forced to shop while my luggage made its way around Germany. I saw the shirt, loved it, and to this day, am not sure why I hesitated.

    I agree with Kathy on the pants, but they do have a wonderful texture and weight. I liked how your ponytail peeked over your shoulder in the one photo – just a reminder that hair isn’t always so no-nonsense.

  3. Perfectly put together, and I love the purple gingham blouse. I have a similar cashmere sweater that I wear quite often to work. Can’t go wrong with that outfit!

  4. Your work outfit hints, that your work place is filled with men ;)
    Ok, I might be wrong, but you definitely look like you are serious about this job. Just as I´d expect you to be.
    Good for you!

  5. This is what I would wear too. A suggestion for pants-try Talbots.
    I just discovered a great fitting style that sits comfortably at the waist and does not stick to my thighs–called the Heritage.
    Have fun at the office…you have not mentioned what it is you are doing now?

  6. I love you with the glasses! I can’t wait to read more about your spin on business casual.

  7. You look smashing, I think the ensemble sends a great business message, you clearly have come up with some stellar parameters during the last 2.5 years.

    Have an utterly divine week at work!

  8. Love your outfit! I look best in blue and only recently started wearing reading glasses at the office (ah, the joys of 30) and I went and got a lovely pair of Skaga ‘Amy’ in purple! I have fair coloring like you and they really add a pop of color to my face. Nothing like purple combined with the current nerd chic trend, crazy-like indeed!

  9. If I were a new colleague of yours, I would have the best of times reading Privilege and seeing what your interpretation was of the clothes you had worn the day before. It’s one of those questions one can’t ask: “where did you get that lovely X?” is fine, but “why are you wearing that particular outfit?” is beyond the line. I hope you had a soaring, smiling first day!

  10. First, you are impeccable and divine.

    But, dadgummittall I can’t see your FEET. Ever since you wrote that you’d gotten new socks for the new job, no way could I imagine how socks, old or new, would be going to work with you, lemmie see those feet next time please!

  11. You look wonderfully polished for a business casual outfit! I know you will soon be invested in the culture of the company and be a well thought of employee. As a recently gone gray, looking great fifty something, I have one thought for you. We both have similar coloring with skin, hair and eyes. I have found it imperative to define my brows, especially when wearing glasses. I use Anastasia brow gel in charcoal. It makes a huge difference in avoiding the washout.

  12. What a wonderfully classic outfit. Would you believe I dressed like that over 35 years ago? Chanel said it best: Fashion fades, style is constant.(paraphrased)
    You certainly have loads of style!

  13. If you showed up as our project director, I’d be very inclined to respect you, just based on first impressions. And my male colleagues definitely would. No one would look askance at your hemlines. :) Hope you’re having a good first day back at work.

  14. Really appropriate yet interesting outfit: it’s the purple gingham, it’s excellent !
    Business casual is the devil but you’ve mastered it.

  15. Well played on the back-to-school ensemble *claps*. The purple gingham is the magic link here, with those terrific non-colored glasses running a close second. Can’t wait to hear more on the new job front.

  16. Loved both posts. Think you looked polished and happy. Shiny happy people make a good workplace swing.

    I have on the florists version, a red and white gingham from the Gap, a grey v neck sweater from H&M and a pair of straight legged jeans from Nordstrom’s junior dept. No make up but newly cut and blonded hair.

    It’s a dirty job but someone’s gotta do it.

    xo jane

  17. I like this look. It’s like you put on the clothes and then you can forget what you are wearing, no bows or wrappings to come undone or be bothersome. You are all business and can perform your duties with confidence!
    Hope that your transition is going well.
    My son is down in your neck of the woods for a conference…who knows you might rub elbows!

  18. I think that’s a pretty good first-day outfit.

    It’s good to lay low in the beginning until you get some traction, so no need to dazzle anybody with your style just yet.

    Hold onto the too-big pants. There is something about spending all day at your desk that lends itself to 50+ y/o women needing a little extra room in the seat :(

  19. Oh Lisa. I am applauding. That first day ensemble is right from top to toe. Agree with previous poster that a wee bit of shirt cuff (say a quarter of an inch or so) does something to make the pullover seem a more intentional part of an outfit. It’s not a make or break kind of thing. It’s a tip from men’s tailoring that I employ regularly. Try it next time and see what you think. In any case, I’m sure your new co-workers smiled genuine smiles when shaking your hand for the first time. I love that you didn’t do khaki, black or dark wash denim trousers for your first day. I’m dying to know what handbag(s) you carried and what you did for lunch.

  20. Casually elegant. Understated, yet defined.

    Probably no one in the office noticed the slacks, as you were most likely in motion or seated throughout the majority of the day. Better a bit large than too tight.

    I find the gingham appealing, too, and in lavender, it’s an inspired choice.

  21. You, as always, look fabulous and capable. I am starting a new job tomorrow and took a break from staring at my closet wondering what to wear to see if you had posted what you wore. Thank you for the inspiration. I will return to my closet with your outfit and my use cases in mind.

    I am at the other end of the career spectrum and at a more conservative office, so I think it will be grey pinstripe suit, low heels good for walking and meeting/greeting, and pearls. Shirt tbd. Thank you, as always, for your guidance.

  22. I don’t have a job yet to wear nice clothes to, but I’m meeting a friend to go to a museum and lunch — and since this is Madrid, that means I can gussy up a little.

    I love your glasses — tortoise is a nice defining space on those of us who are generally pale. My new specs are tortoise in the front and turquoise in the back. Sitting the fence between serious and arty. You might want to try a two-tone frame yourself…

  23. Hello Sturdy Gal! Your outfit is much like mine – only that you have lost weight, no? The pants seem as if you have lost 6 pounds at least!

    Cashmere v-sweater, pants, shirt – works everywhere and at every age. The cashmere sweaters I bought last year at Benetton went up from 115 EUR to 135 EUR within a year. Glad I bought 2 of the same kind. They never let you down.

    Since were are dressing alike and both wearing glasses – did you consider wearing Silhouette / frameless glasses? I have been wearing frames forever and plan on going frameless, soon.

    I would love to see your hair from the back – the ends must still be blondish, no?

    Oh, and not to forget: which purse?!!! The vernis from LV? I can’t see you taking the LV to work at the first day. Too much of a lound appearance, no?

    I am excited about your next steps. xo Paula

  24. Good choice for a first day – love the bright touch of the gingham. The link back to your early post makes me wish I had discovered you sooner.

  25. I think you look very polished and pulled together but not too uptight. I am sure the shirt and the necklace provide the perfect counterpoint to the seriousness of the rest of the outfit without going too far.

    The advantage to the darker glasses is that they bring some of that attention to your face, balancing the strong clothing, and drawing attention to the intellignence in the eyes, whereas otherwise all the detail disappears into paleness.

    1. That’s a good point! Frameless glasses would probably not work together with light eyebrows. An eEye-brow pencil, eyebrow-shadow etc might balance the change though. Which would be more of an effort … So many choices!

  26. The outfit is fine, but I have a question about your hair. I am not attempting to be rude. Why have you chosen not to have it cut in a softer style around your face? Is pulling it back so severely like that a WASP thing? I just think letting your hair flow in a face-framing way would look so much prettier. Again, hope I do not offend–genuinely curious as to your thought process here.

  27. Kathy – That is just wild, the alignment of our recent shopping:).

    Susan – Oh exactly as I hoped. Thank you.

    Jamie – I take it as a compliment:).

    frachellea – Thank you for noticing the ponytail. The hairstyle really isn’t as severe as it appears. And it’s lovely to have gingham in the fall.

    Jen – Thank you!

    James – Thank you. Yes. I think so.

  28. Mette – Yes, high technology is like that. And yes, I am serious about my work. Serious and happy.

    Calie – Thank you!

    Marcy – I see you found my job details. Talbots, huh? I will give it a shot. Clearly I need remedial pants help:).

    Dawn – Thank you! Those would have been on my design docs for the day’s clothing, had I written them.

    Miss Mindless – I plan to keep talking! Thank you.

    Muffy – Oh thank you. I feel a little flutter of nerves, but not even close to how it was in my younger days.

  29. TPP – Thank you very much.

    Ida – I work in software/the internet. It’s a very casual environment.

    A Girl – Thank you!

    Monica – Thank you! And purple? Really? Perhaps that will be my lesson for the next year. Learning to wear purple glasses:).

    Gold digger – Thank you.

    Patsy – Ah the cuff out. So classic.

  30. Flo – Well thank you ma’am. The socks are plain black trouser socks. Just to make the walking comfortable, and minimize visual impact.

    Marguerite – So interesting. I actually thought, as I was getting ready, that I might need some eyebrow something. But since I never do it, I left them alone. But I will start experimenting.

    That’s Not My Age – That would be so stylish. Really. I’d probably have to play up:).

    Naurnie – Thank you punkin.

    Sandra – I do believe that you dressed like this – it’s not trend-bound, and I can see your design sense translating to a wardrobe like this.

    Staircase – Aaah! So wonderful! Thank you. Yes, it was great.

  31. Stephanie – Thank you.

    DaniBP – Thank you, especially in light of your color sense. I think I’m like Daniel Webster, having a talk with the devil, before I could maybe argue him down.

    QBS – Getcha some, right?!?

    Melissa – Thank you very much. I’ll be right here.

    Jane – I love that there’s a florist’s version.

    Hostess – That’s it! Exactly it. I have kept my eyes peeled but I don’t see son of hostess:).

  32. RoseAG – Hahahahaha. I will work on traction and try to counter-act middle aged seat with the walking:).

    Sylvie – OK. I will think about the cuff. But I laughed out loud when you said that about the other kinds of trousers. Tuesday I wore the dark wash:). For lunch, Indian. And the LV, but it went into my office quickly and stayed there.

    Else Louise – Thank you. Yes, work is primarily a shoulders and up game:). I liked the purple + gingham too – kind of oxymoronic.

    Peach – Twins! I think it’s going around:).

    R – I am happiest always when useful. I will keep on posting these business casual outfits. We will wrestle this beast to the ground.

    Mater – Thank you! And yes, I am committed to this blog and I can’t help but take my commitments seriously. I am sure you know what I mean:).

  33. Rubi – Tortoise hybrid. Hmm. Good idea. Enjoy Madrid.

    Paula – I have yet to figure out the pants conundrum. Possibly I always wore them big. And I did bring the LV, because of logistics, but I put it in my office and there it stayed for the rest of the day:). Yes, the ends of my hair are blondish still.

    MJ – What a wonderful thing to tell me. Thank you. And if you ever think, wow, I wish she wrote posts more like those early days, just let me know. I take my guidance from you all.

    Mardel – This is so good to know, about the glasses. I have worn them so obliviously, until now. And of course pulled together but not uptight was exactly what I intended.

    HijabEng – Oh, thank you. For the compliment and for the link! Cool glasses.

    Wilhelmina – You are not rude at all. The hair is primarily for convenience, and professionalism. Pretty isn’t at the top of my list right now. But I’ll do a longer post on the hair, soon.

    WorthyStyle – Thank you!

  34. I jsut stumbled across your blog and as I work in software I was interested in what you would choose for your first day. Every company is different but though my wardrobe is casual and you have many nice pieces — I could never dress like your “whole look”. In my company, I think that look would be associated with a possible lack of imagination. Obviously the industry is very casual, no suits needed…but if you look dull…none of us would make the cover of W.

    I’m sorry if this sounds harsh. I am sure you will be very succesful in your new job and your blog is great. Best of luck.

  35. Yikes, had missed this big news, was away for 2.5 weeks. Read all your posts since Oct. 8; congratulations and wishes for a stimulating and satisfying experience!

  36. Very nice, Lisa! Purple is a great color on you.

    Not sure the brown eye glasses are a good match for your coloring. Dark grey, blue, or lavender would be more flattering to your complexion. I think you are brave to go gray while you are still working. I am your exact age and experience so much ageism in the work place that I have decided to have my hair colored until I retire.

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