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  • Writer's pictureWhitney Wisdom

My Actual Boyfriend's Jeans


His pants, my outfits.

Boyfriend jeans have been around longer than you think. The first consistent wearer of the slouchy, not-my-own-denim look was Marylin Monroe. Her 1961 film Misfits portrays her as a style icon for both men and women alike in her all-American Lee’s denim jacket, white collared shirt, and of course, Levi’s boyfriend jeans. The bombshell was anything but masculine yet, wore the identical look as resident bad boys James Dean and Marlon Brando. In 1961 Monroe was newly divorced from playwright Arthur Miller and had several affairs including Mr. Frank Sinatra. Whose Levi's did Monroe sneak into her bureau? That’s one mystery that remains.


Marketers are paid to be quick on picking out and exploiting trends. Flashforward to the past decade or so and “boyfriend fit” flannels, hoodies, jeans, t-shirts and even blazers are all we see. Retailers cleverly emphasize that oversized equals comfort. If I wanted a t-shirt that was more of a tunic style that hung to my knees I would typically just buy a bigger size or even a men’s size. I appreciate the wide range of fit options in the market today, I really do, but buying “boyfriend jeans” from Madewell doesn’t give me the same satisfaction as styling my actual boyfriend’s jeans. It seems fake. Style is synonymous with honest authenticity. I want clothing that already comes with a real story.


I decided this petroleum stained denim was crying for a woman’s touch. These jeans were inches from being tossed forever, so I gave them CPR by trying them on and glamming them up. Of course a size 4 woman wearing real men’s jeans presented some fit challenges. But, I pressed on and realized...


Boyfriend jeans are greater loungewear than leggings. Please quote me on this.

Boyfriend Jeans are Great for:

  1. Tucking in your Shirt: This fills in the waist and prevents sag. Also if you were waiting around for a time when you need a cute belt, boyfriend jeans are the reason.

  2. High Waisted: Even if the jeans weren’t high waisted on him pull ‘em on up so the crotch doesn’t, um, hang. New game: how high can you go.

  3. Cuffed Hems: Short girls don’t even consider this a tip as cuffing the bottom of their pants is a daily occurrence. As someone built like a spider, the first thing I noted was the longer length. Of course you can always have a tailor hem the bottom however, a loose cuff adds to the carefree shape. Single cuff, double cuff, rolled into capris - just make it you.

  4. Frayed Hems: If the denim is not too long get crafty and let out the seam for character. Pull the seam down under the arch of your foot can create stirrups to help keep your pants in place. No one will see if you tuck into boots or high top sneakers.

  5. DIY Light Wash: Several years ago (like 2007) I tried to sand the thighs and knees of my flared jeans for a faded look. After using a pumice stone that didn’t really do anything, I found sandpaper in the toolbox. It was too gritty and left the denim white and thin. Men’s pants are made for all the dumb cowboy things they do (like backflips and yardwork) and therefore can survive a rough sanding!

  6. Dukes: When you and your boyfriend are completely different shapes and sizes, play designer and chop the denim into shorts. I recommend measuring the inseam of your favorite pair of shorts before cutting, to be sure of the length.


Styling: Before I buy a new item I brainstorm ways I can wear it and how this new piece would fit in with my existing closet and jewelry box. Same goes with clothing I acquire. Think: how can you make it personal?


Classic Baggy BF Jeans: To make my overly worn boyfriend jeans appropriate for everyday life, I amp up the feminine factor with a floaty camisole and fluffy cardigan. Add a heeled sandal or bootie to help your legs not get lost in the bagginess of your bf’s pants. Don’t get it twisted! They may be his pants but this is my outfit.


Feminize baggy stained denim.

Ultra Wide Leg BF Jeans: Let wide ride with slim low top sneakers on the ground floor plus an easy tucked-in t-shirt on the upper deck. This is the most unisex way to wear boyfriend jeans. Direct comparison time! Who wore it best?


Boot Cut BF Jeans: Dark raw denim with a bell bottom requires suede fringe boots. This is a fact of life. I agree, it can be tough to get into the “blazers for casualwear trend,” but I found pairing a light spring colored blazer - sans undershirt with boyfriend jeans, booties, a cool purse (Tie on a vintage scarf while you’re at it!), and a scrunchie is a winner.


Testing, testing...1,2,3.

It Doesn’t have to be Your Boyfriend: Single people you are not left out on this fashion trend! Actually, you’re in luck because now you can shop for a boyfriend who wears about the same pants size as you. (Kidding...kind of!) Maybe being at least 6 feet tall should not be the cornerstone of your dating hunt. But real talk: any men’s jeans can create the boyfriend fit.


Not everyone has a boyfriend who’s name rhymes with Levi. I get it.

P.S. it’s not just about boyfriend fashion. You can gather inspiration garments from everyone in the family. Obviously “mom jeans” have come to be equal to boyfriend jeans. Though also a straight wide leg, mom jeans traditionally have a more faded blue wash - the kind your mom actually wore when you were a kid. (I’ve found some great inspo in Boy Meets World, just throwing that out there.)


Grandmother’s heirloom jewelry has always held high meaning - ARTICLE HERE. However, the next thing you’re going to want to pull out of the attic is your Grandfather's point collar, zip front, neutral tone, polyester jacket. I’m sure you wore it as a little girl when the restaurant was too cold.


Stealing your man’s sweatshirt is amateur when you’ve got his full worn-in jeans collection to loot through.



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mark1618
mark1618
Feb 22, 2021

I love every word of this. You tell a story that even holds the attention of Grammies in a size 4!! Love all the pictures. Both of you should model for a magazine in your spare time, not any!! The jeans look great on both of you, but both of you can make most things look as sophisticated and relaxed as you both are in your own skin!! Keep up this great work

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