Lawyer Fashionista: Letting Your Freak Flag Fly

Not too long ago, I went to a birthday party for the father of a dear friend. Harry turned 90, and he’s a great guy. The party was held at 21 Club in Manhattan, and in preparation, I wore a blue suit, white shirt and tie. When I arrived at the party, all but the under-25 crowd of males wore suits. There were only two of us wearing a tie, me and an old friend, Gene. While a few wore sports coats with open collar shirts, most wore suits without ties.

Neckties are silly affectations, but they distinguish more formal dress from less. And, for guys, they’re the only aspect of more formal attire to reflect any personality. Pocket squares make you look like a dandy, trying to be Roger Stone with his desperate whiff of “look at me,” but ties remain within the normal paradigm of things men wear when they’re dressed for business.

But not for long?

This sort of thinking suggests that the very act of a woman offering up a fantasy of manhood in an arena dominated by male fantasies of women can be a revelatory gesture. If men’s ideas about how a woman should dress have at times felt constrictive — “He doesn’t dress women, he upholsters them,” Coco Chanel once said of Christian Dior, whose postwar wasp-waisted New Look shapes heralded a return to more traditional female silhouettes after the liberating advent of women’s trousers — the impulses of the women currently at the forefront of men’s wear are by contrast generous and freeing.

Waight Keller’s couture collections use finishes long associated with women’s wear (sequins, delicate floral embroidery) that encourage men to experiment with new identities, and at the Row, the Olsen sisters are creating men’s suiting so sublimely minimal it is almost self-effacing, as though its wearer has more cerebral concerns than tailoring.

Similarly, Hearst says that her ideal customer is, above all, a man with “a modern brain,” someone who is engaged with the issues of our time, such as climate change — the brand exclusively uses biodegradable packaging — and dissolving gender lines altogether. If men have historically designed for women as they think they ought to be, these women are designing for men as they hope they might be.

Why women care what a male fashion designer says they should wear eludes me. Wear what you want. Wear what makes you feel good. Wear what’s comfortable. Wear what you think you should wear, whether Christian Dior approves or not. And my guess, though I can’t be entirely certain, is that Dior doesn’t check to see what you’re wearing and doesn’t really care about you at all.

Then again, as Dr. SJ reminds me when I ask her what to wear for an evening out, “It doesn’t matter, no one looks at you anyway.”

So who is this ideal customer with a “modern brain”? We’ve seen more than our share of outlandish efforts to dress men like little girls and members of the Lollipop Guild, but this is more serious, raising the question of why women are underrepresented in the design of men’s wear.

It’s a persistent disparity. In 2017, 85 percent of the students enrolled at New York’s Fashion Institute of Technology were female, but in 2015, only 14 percent of major clothing brands had a woman at their head, according to a Business of Fashion survey. Though fashion, like so many industries, is beginning to reckon with the consequences of longstanding and deep-rooted gender imbalance, female designers are still in the minority, and women making clothes for men are a rarity.

There is, of course, a hole in the statistics that presumes the “deep-rooted gender imbalance” in the fashion industry reflects a problem with women making clothes for men as opposed to women designing clothes for anyone. But it’s true that it’s a rarity. So, let’s see what’s what if men wore what Gabriela Hearst designed.


Not terrible, sneakers aside. But then comes the nitty-gritty.

Are you out of your mind? On what planet would a guy spend $7,325 for an “outfit”? And one without a tie? For a grand, you can get a custom made suit and they’ll throw in a half dozen free shirts, all of which will fit properly as opposed to those jacket sleeves that fall a couple inches short of the wrist, leaving you with enough money in your pocket to buy a really nice tie and, dare I say it, a decent wristwatch.

If you don’t care to wear a tie because it’s too constricting, too rigid, too “male,” then don’t, although judges will look at you funny and, even if they don’t say it aloud, wonder what you have against the uniform. Some will send you packing and tell you to come back when you’re properly dressed. You can argue the point, but given that judges get to decide your client’s fate, it might not be the hill your client wishes to die on.

As for me, I’ve got nothing against whatever it is women designers like Gabriela Hearst are selling, but I’ve also got no interest in buying it. It’s not just that it’s a foolish use of money, but that suits without ties seem silly and pointless. There may be no functional purpose to wearing a cravat anymore, but sometimes you just have to let your freak flag fly. Ties may not be in style, but that doesn’t mean they’re not what a guy wants to wear.

38 thoughts on “Lawyer Fashionista: Letting Your Freak Flag Fly

  1. Chris Van Wagner

    Given that the modern men’s necktie has its origins in the cravats of foot-soldier mercenaries in a 30-year war, they should be required attire for any criminal defense attorney regardless of gender. After all, are we not akin to those Croatian soldiers for hire, enmeshed (for a few Francs and some bubbly) in a decades-long battle of a similarly futile nature? See, e.g., And thanks, French King Louie the 13th. I like my ties.

    [Ed. Note: Rules notwithstanding, this link is approved because it’s something you need to know.]

    1. Kathleen Casey

      Regardless of gender? Not to me. It has never occurred to me to wear a tie. I always knew I was female. Heterosexual too. Besides, I read long ago that a tie is a phallic symbol and so it looks odd on women even though we may not realize exactly why. Plausible.

      1. Chris Van Wagner

        I may or may not have succumbed to Madison WI culture wars with that reference to gender. Or I may have been secretly trying to mock them by eliciting comments like yours. Let me loosen my tie and …. wait. Never mind. I never loosen mine in public. #oldschool

  2. Hunting Guy

    Make a fashion statement and wear a bolo tie.

    Or would that be cultural appropriation?

          1. C. Dove

            The only lawyer to wear a bolo tie in San Francisco (Frisko, please!) was named Jasper Monti. He and his bolo tie (with salmon-shaped tie clip) retired some time ago.

  3. Bear

    I and my tie collection thank you, even though my wife assures me no one looks at me either.

    1. SHG Post author

      When I look at the number of ties in my closet, I harbor suspicions that when I close the door and it’s dark inside, they reproduce on their own because there’s no way I bought that many.

        1. SHG Post author

          On the one hand, some things go without saying. On the other, there’s always someone who feels the need to say it anyway.

      1. Hunting Guy

        There’s actual a life cycle for them.

        Have you ever noticed that you have an abundance of pens one day and no paper clips but the next day you can’t find a pen but there are all the paper clips you can ever use? And then when you need a paper clip, you find ties you can’t remember getting?

        One species had clothes pins as a larvae stage but they died out as clothes driers became common.

  4. Mario Machado

    Nowadays, in Miami at least, only old-timers and me wear ties to depos and jail visits.

    I beam with pride when I see a 60-something walk in to Miami FDC wearing a full suit. I am not an island, after all.

    1. Skink

      Mario–I’ve worked the Swamp for a couple decades. I never counted the ties in the chest, but there has to be nearly as many as golf shirts. There’s 102 of them. Since I fired all the firms which had the dopiness to associate with me, the uniform comes out only for court appearances and mediation. There is probably no living person that has seen all the ties worn.

      But I was once denied entry to FDC-Miami because I wore khaki pants–the idea was they looked too much like the inmate uniforms. A crusty Southern District judge was very much unhappy that they didn’t let me in. I guess a suit would have been better.

  5. rxc

    I am almost 70, retired for 13 years, and I still have a few ties from the days I was working. I have also purchased at least 2 ties since I retired, because they appealed to me. One of them has a “periodic table” (chemistry) pattern, while the other is Santa on a sailboat. So you know where I come from. They are useful for a few events where I have to “dress up”. Otherwise, I wear the standard FL retired guy uniform – shorts, T-shirt, Crocs/boat shoes. When it gets bitterly cold (think 55F), I put on a flannel shirt.

    It is liberating to not have to worry about clothes any more. Keep one set for funerals, weddings, and other special occasions, and otherwise wear only clothes that are (1) functional (keep me dry/warm/protected), (2) comfortable, (3) decent shape/appropriate for the occasion. In that order.

  6. phv3773

    At my last attempt, I still had muscle memory of how to tie a tie. I’m not sure I could still describe it for someone else.

  7. Rxc

    Left coast? Goodness no. I like to sail on a real ocean, not a little bitty shallow bay you can almost wade across.

  8. Dave Landers

    I met a woman at a bar the night before. She mentioned she was originally from Croatia. I mentioned to her that the necktie originates from Croatia. She was impressed and explained where the word came from by pronouncing Croatia in such a way where the second sylabbel sounded like tie.

    As the night continued on, my charm was fleeting. And she fled.

    I will always have my necktie as time goes by.

  9. Dudeman

    There was a judge in Milwaukee County Circuit Court who did not consider an ascot to be sufficient:

    [Ed. Note: Link deleted per rules.]

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