How to Wear Office Trousers Without Looking Like a Stockbroker

No, I will not move my meeting up to 4!


Here’s a recurring question among the denizens who dwell between the four walls that encapsulate the team that is Man Repeller: How do I wear trousers while still feeling like I look cool?

Now that we know “cool” does not have to be the end-all-be-all trait to aspire towards, the question takes on new meaning. How do I wear trousers while still feeling like I am representing my best self? Of course, to answer this question, you must have at least a vague sense of what it means to feel like your best self.

If that self is a cross between Bianca Jagger, a financial analyst and someone who seems, I don’t know, just too tired to take a shower or whatever, you might want to consider…

Sally Lapointe tank, Isabel Marant pants, Marni earrings, Jennifer Fisher necklace, Chanel loafers

A sequined tank, under-eye bags, forgiving trousers that dutifully allow for high-sodium-content meals and a necklace that dances across your collarbone as opposed to your cleavage.

If, however, your best self is actually a cross between Larry David, Iris Apfel and the guts your mama gave you, try…

Leandra Medine Style Trousers Man Repeller-32

Ellery jacket, Rosie Assoulin T-shirt, Golden Goose sneakers, Warby Parker sunglasses

A full suit worn with running sneakers. But not just any suit! One with vaginal ruffles climbing up the sleeves because, duh, reproductive rights. I was going to wear New Balances, but I didn’t. Feel free to add your own flair.

And finally, if you wish you lived far away from the Americas, but ended up living someone else’s life here on a trading floor, why not wear…

Leandra Medine Style Trousers Man Repeller-19

Muzungu Sisters caftan, Creatures of Comfort pants, Walk of Shame trench coat — similar here, Gucci sandals and Hermès headscarf

Loud enough and long enough clothes to completely obstruct the presence of your stockbroker pants.

So there you have it, ppl. I’m done.

Photos by Krista Anna Lewis.

Get more Fashion ?
  • that second outfit is SO GOOD

  • Katie

    Where are the trousers in the second out from?! Fantoooshtic!

    • Leandra Medine

      a brand that doesn’t really exist anymore called mina and olya 🙁 their stuff ruled.

  • Aesthetically Amber

    The caftan outfit is perfect because I always like the ideas of texture, pattern and colors while finding a balance between flowy and fitted pieces. Sometimes, its hard to deem what appropriate for the office with colors and prints without looking too casual.

  • Natali

    That first combo is one of your best outfits to date! Bomb dot com!

  • Hilary

    These are instantly some of my favorite looks of yours, ever. I’m most identifying with Look #2. SO GOOD. (Also kinda aspiring to be Look #1.)

  • Zsofi

    I love the first two outfits, the 2. is genius! I like the structure of the last one too, looks supercool on you, but too many prints for me. I wear these kind of trousers all the time with a vintage t-shirt and blazer and Vans. Or with a shirtdress/under a slipdress with ankleboots. Oh and short faux fur coats are heaven with them as well as belt bags!

  • Sofia Allyn

    Leandraaaa! How did your fold your Hermes scarf for that headband/baby turban situation?!

    • Leandra Medine

      Oooo, i’ll tutorial it 4 u.

      • Sofia Allyn


  • I live in black tailored trousers. Thanks for the inspo on changing it up, especially 3

    – Natalie

    • Grace B

      curious, have you ever tried out the saks fifth avenue trousers they sell at off saks? i almost tried them but i just wasn’t sure. my dorky and too short black trousers from Macys are jus ugh…

  • patricia Thévoz Ruiz

    OOOh Godessa ! The second one is just wowowow !!

  • Devon Cansada Wade

    A cross between Larry David and Iris Apfel is definitely the person I have been trying to find within myself.

  • chouette

    My corporate office M.O. is to wear stuff that is acceptable enough so that no one can say anything, but weird enough that I don’t get pulled into meetings in front of salespeople. I’m wearing men’s size 56 suit pants gathered up with a belt and a pinstriped wool top from the 80’s with a full-on cape back and I feel ready to conquer/hide from the business world..?

    • Julia

      “Ready to conquer/hide from the business world” ahah same

  • Samantha Lee

    That ruffle sleeve blazer is the best thing I’ve ever seen, and I commend you for looking chic AF in that last outfit because I would never be able to pull that off.

  • Julia

    That rad blazer/sneakers/sunnies combo look is kickass. I might emulate it tomorrow to feel a little extra confident because god knows this week has been emotional hell

  • Grace B

    I recently bought my first pair of Eloquii pants, and while I love the color (dark teal) I find them kinda baggy and totally wrinkled? I don’t think they have any spandex. But then I just remember myself of my girl cousins who have been wearing Talbots and WORKING IT for like a decade each and try to go with it…sweater sets for the win.

  • All too great. The second one looks a lot like my winter slush-surviving outfit. Minus those sleeves, I need something like that!

  • I especially love the first one – it also reminds me how much I wish this type of high-waist, wide and really long pants was the trend and available everywhere (=favorite shops, doable prices). I am so fed up with what goes under business style (ankle-length slacks & Co.) currently… Do I have a chance?

  • lychette

    Hi Leandra, you recently wore a Khaite turtleneck, and I am hoping you could give a little review of it? I love turtlenecks and have been eyeing it for a while at theLine’s webshop, but before I make the investment, I’d like to finally hear from someone who has actually bought a Khaite product 🙂 thanks a lot in advance !

  • Mariana

    Ankle length trousers + sneakers is awesome, really love to wear that look. It kind of says that I’m profesh but cool, formal but love confort, I have to attend that meeting but I also have to run to my pilates class after it.

  • Vida Rose

    These are all adorable. #7 makes my heart sing

  • Ryan

    Leandra and Man Repeller readers,
    I want to start some type of fashion club at my high school. I love the idea, but i want to name it something outside of fashion club….Please reply if anyone has any ideas or ideas of things i should do in the club i would love to hear others opinions!! 🙂 I want to teach girls in my school they dont have to dress like everyone else all the time!

    • Don’t have any ideas for a name but I think you’re amazing and I wish I’d had your kind of guts back in high school where I tried impossibly to fit in instead.

    • Washu Ai

      Let your school think you’re starting an internet club WWW, but let it stand for something like Wonder Wildly Wearables or Wild Wear Well and you can throw in some wonder woman slogans, while you’re at it.

  • Sarah Gbaguidi

    You are so pretty on the first picture ! The first look is my favorite one.

  • bella

    yes! i work in retail atm and have to wear proper slacks and i often go out straight from work so i’ve been on a mission to improve my party attire and the Larry David and Iris Apfel is what i most often end on. tucking a old disheveled shirt of my brothers with runners is my go to, comfy and semi fashionable