How to Wear a Kilt and Not Embarrass Your Girlfriend!

While there are many great things about having a boyfriend, there are still plenty I just do not understand. A few I physically dread. Okay, really only one.

I dread the inevitable day when my boyfriend wears his kilt and I have to be seen with him.


My boyfriend, Harry*, owns a kilt. He loves it. He loves it so much he should marry it spent $250 on it. Dear reader, a query: did you just scream when you read that number? Did that price tag cause you to shoot a drink out of your nose all over your computer screen? If so, I sincerely apologize; and promptly put the blame on Harry. What a silly man to let slip he paid two-hundred-and-fifty-freaking-dollars for a piece of clothing. It is easily the biggest mistake he’s made thus far in our relationship. I shrieked when he told me and couldn’t stop laughing for 10 minutes. In between fits of giggles I did manage to squeak out the words, “I’ve never spent CLOSE to that on an item of clothing! And I’m a girl! Who likes clothes!”

Unlike these fellas, my boyfriend has Italian ancestry, not Scottish. He has no heritage excuse.
Unlike these fellas, my boyfriend has Italian ancestry, not British. He has no heritage excuse. [credit]
You might assume a man who spends that kind of money on a kilt is some sort of fashionisto. For Harry, this could not be farther from the truth. It has improved steadily since we started dating  in the past few months but when I first met him, Harry’s “style” was best described as “Shlubby High Schooler Chic”. That’s how I described it one night in a fit of inebriation-aided honesty, much to my poor boy’s chagrin.
“How many of your clothes date back to your teenage years?” I demanded, “I suppose it’s superficial, but I find you much more attractive when you look like a man and not a teenager.”
“When you put it like that, it makes perfect sense,” he acquiesced.

It’s not that I have anything against men in kilts. I’ve always found value in breaking convention. I’ll be the first one to say there is something sexy about a man who rocks a kilt. I believe Harry can get to that point, and when he does, I’ll no longer dread summer. I’ll happily walk down the streets with my kilted fella. I’m just scared he’s not there yet… In researching this article, I looked at every picture on Facebook where he is wearing a kilt. In every single one, I swear I’m not exaggerating, he is wearing a tie-dye t-shirt. An article of clothing approximately 100 times less expensive than that on his lower half. Irony?

How to Wear a Kilt

I can pinpoint it to this: The subtext of a man wearing a kilt should say, “Yes, I’m a man. Yes, I’m wearing a kilt.” If the outfit instead reads: “I don’t want to wear pants”, I’ll never find it attractive.
To illustrate:

This guy looks great, no? Classic, cool, kilted. Subtext: “I am man enough to wear a kilt.” He is, he’s rocking it. [credit]
In contrast, we have Mike Myers in a look that screams, “I don’t want to wear pants!” The t-shirt is almost as bad as a tie-dyed one and the shoes and socks are appalling. Every date night, this is my biggest fear. [credit]
Call me crazy, but I’d rather not be on the arm of a man who at first glance inspires the thought, “That dude’s not wearing pants.” As illustrated, this really doesn’t have to be the response to a kilt! But I suppose I should be thankful. As much as I hate the old shlubby t-shirt look, it could be so much worse. At least Harry has never worn his kilt in an outfit where the subtext is “I’m a shlubby potato sack”.

A fun thing to say: my boyfriend looks better than Ed Westwick. [credit]
7th Annual "Dressed To Kilt" Charity Fashion Show - Runway
Proof that there are some outfits even models can’t make look good. Seriously, wtf? [credit]

Or “Look at me, I hate clothes so much I’ve chosen to make a bath towel an outfit! Then I got cold so, duh, I put on a scarf! I may be gorgeous but by wearing this outfit I prove there is nothing going on between my ears.”

Then there are some men who are man enough, so comfortable with their sexuality that they’ll wear pink AND a kilt. This is impressive.


Or it would’ve been if he hadn’t gotten scared at the last minute, worried it was too girly, and added the sword. Really, Gerard Butler? If YOU need to compensate, what are other men supposed to do? Well for some, they can feel awesome knowing they’re more confident than Gerard Butler. This guy is my favorite.


Instead of screaming “I have a penis!” by carrying a sword, he emanates, “I am handsome, intellectual, and talented. I’m a giving lover and your mother will love me too.” Boom: kilted dreamboat. See, I have no problem with a t-shirt when it’s not shlubby! Keeping it simple, totally manly, that’s sexy.

Of course, if you really want fashion advice, you look to the gays. Want to know how to wear a kilt in everyday life? Just ask Marc Jacobs:

Do you like your significant other’s fashion choices? What are your thoughts on kilts? Think they’re sexy? If you’re a dude- would you ever consider wearing one? Ladies, would you ever date a man who wears kilts? Ideas and advice on what to wear with a kilt?
Oh, and just because it’s always a question: no he doesn’t wear anything under.

*I will call my boyfriend “Harry” in an homage to the Sex and the City character and because he has a lot of hair. Of the chest variety as well as on his head which he usually wears in a ponytail reaching well down his back.

None of these images are mine, click photos for credit/Featured image link: credit

About New York Cliche

NYC lifestyle blog by Mary Lane. Events, adventures, epic mistakes, dating, life, humor. A 20-something trying to make it (and make out) in the city of dreams.

11 thoughts on “How to Wear a Kilt and Not Embarrass Your Girlfriend!

  1. I met the tall and handsome newscaster Peter Jennings some years ago at a party. He was wearing a kilt and told us a kilt story. An American woman asked a Scotsman, “What is worn under your kilt?” He replied, “Nothing’s worn at all, Madame. Everything’s as good as new.”

  2. My boyfriend’s fashion choices….if I didn’t love him so very much, that might be a point of contention. I like well-dressed guys….really, really like them. And my boyfriend tends more towards…jeans, t-shirt, ball cap. Now when I can manage to get him into something a little nicer, he cleans up oh so well. I’m pretty sure he would never be caught dead in a kilt.

  3. I approve of the significant other’s fashion choices because when you’re dating someone your size and your gender, you really should dig their style to maximize wardrobe. That being said, is a kilt like a skirt or a skort? I always thought it was skort-like…in which case, I would be anti-kilt because if you’re going to skirt it, skirt it all the way.

  4. Is it tartan? If so how did he choose since each tartan represents a Scottish clan…
    My Grandfather was Scottish and you still have to throw a black tie event before they’ll wear their kilts, even then it’s a long shot.

    1. One was a utili-kilt, have you heard of those? That was the one he spent an insane amount of money on. He did have a wool tartan, it would have been a good question how he picked the pattern. We no longer speak, so now I’ll never know! Thanks for reading!

    1. Dear Ross, I am so sorry about this. I do not know why the link to your image did not work in the past. I have rectified the over sight and sincerely apologize! I do not have record of you previously contacting me, so I am sorry this was not done sooner! It is a fantastic image and now has the credit it fully deserves.

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