Ask Allie: Too Old for Boyfriend Jeans?

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I love the look of boyfriend jeans, but I am 65. Am I too old to carry off this look, or is there a way to make them look age appropriate? I am fit and lean, but I am not ashamed of my age and do not wish to look as though I am dressing too young. Suggestions?

On-trend denim is a great way to update your look, no matter your age. The beauty of denim trends is that because jeans are so popular, the trends are quickly modified to flatter a variety of ages, figures, and lifestyles. The other day my mom came over and she was wearing a straight cut denim that was widely cuffed to the “boyfriend” length and the effect was modern, stylish, on-trend, but not too youthful and not at all inappropriate. I chose a similar boyfriend jean style for you, but in a dark wash that will look great now, and as we transition into fall.

french chic

For this look I did a variation on one of my favorite looks – a Breton striped tee with a contrast color accent. The dark jeans and the classic stripe look even more fresh with a pop of hot coral. A drapey cocoon cardigan like this is quite versatile in that it can be paired with a same-color shell for the office, slipped over a simple sheath dress, and worn three seasons out of the year. Paired with classic Repetto ballet flats, this look is fresh, modern, and appropriate no matter your age.

disco chic

A “boyfriend” jean can be dressed up or down quite nicely; I often wear mine with high heels and a sparkly top for a night out on the town. A jewel-toned dolman top looks modern with bold gold jewelry; low wedges in leopard print are comfortable but also show you are aware of trends and know how to make them rock at any age.

rocker chic

Who says that rock and roll is only for the young? This outfit was inspired by all the amazing music lovers of all ages that I met recently at the Forecastle Music Festival. Pairing a favorite band tee shirt with dark denim and a crisp tailored white blazer makes the ensemble sophisticated and chic. This length of jean looks great with a slim canvas sneaker and makes it an outfit that would be fantastic for sight-seeing or lots of walking and standing.

boho chic

You stated that you are fit and lean, which means you can totally rock the long top with cropped jeans look. A crisp cotton caftan looks modern and fresh with dark cuffed jeans; continue the boho look with flat leather sandals, beaded bracelets, and a pair of classic-cool aviator sunglasses.

My goal with these ensembles is to show you that age should not determine what trends you can and cannot wear. Boyfriend jeans as well as all other popular fashion trends can be incorporated to feel comfortable, chic, and age-appropriate. Instead of ruling out a trend, try it in a variety of cuts and shades for an appropriate version. Fashion trends aren’t as black and white as they were a couple decades ago so you can alter them to fit your style, age, and life. There’s nothing wrong with choosing a version that is a bit looser, a hair longer, a less dramatic wash or color, whatever makes you feel confident and fantastic. You can wear hot trends without having them wear you!

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  1. I love my boyfriend jeans but still trying to figure out the best way to style them. I’m quite busty, so I don’t do jackets/blazers and no high heels for me (I miss great shoes). I’m a curvy girl, but I rock my curves!


  2. Awesome! I would never put boyfriend jeans in classic outfit. For me boyfriend jeans was the most casual option, but I was so wrong… And necklace from 2nd outfit is gorg!

  3. I was just asking this question myself. Great answer, I love your suggestions. How about a black moto jacket in a soft fabric? Would this be over the “age” edge for a 52 year old? I would love to put that together with a pair of the dark boyfriend jeans but I am always trying to be careful of my age and inappropriateness.

  4. Fabulous, fabulous, fabulous. The writer has gotten wonderful suggestions from you. I am 64 and would wear any of the above. I prefer straight leg or skinny jeans or trouser jeans in a dark wash, but I would happily wear any of the above capsules. Thanks for not seeing us (Boomers) as fossils. And please let the writer know that as long as we keep it classy, we can do just about anything!

  5. thanks for this, Allie – love your outfits, esp the “Frenchie”! I am 58 and love wearing boyfriend jeans.

  6. I see mature women wearing boyfriend jeans and looking great. I prefer that look to the ultra-skinny jean in some outfits because it’s more beachy-weekendy to me.

  7. Yep – right on ! I am very wary of wearing things that are too young – I just think women look ridiculous when doing so. But, I LOVE my boyfriend jeans that I wear cropped with a tiny cuff. I think the trick is to make the outfit purposeful, so at 40 years old, I wouldn’t wear boyfriend jeans with a t-shirt with a unicorn on it, for example. And crtfly, yes – arch supports make flats much more comfortable. I have killer plantar fasciitis and am never without my superfeet inserts for dress shoes.

  8. Spot on, girlfriend – from an about-to-be-55-year-old who loves her dark wash boyfriend jeans! I wear mine with long tops and with Ts & blazers – although I go with Ts with nothing on them, and that’s an age thing! – so I really love seeing new ideas – totally trying the Breton stripes and cocoon cardigan soon since I have both already. Sharing this on my facebook biz page 🙂

  9. I bet your Mom looks great in her cuffed, straight-legged jeans! Although your letter-writer is slim and fit and likely wouldn’t have waistline issues with the style, for me it’s the waistline of boyfriend jeans that is hard to fit properly. I usually have to wear a belt and that adds bulk in a spot I’d prefer to avoid.
    Shopping for jeans with a friendlier-to-a-middle-aged waist -which would mean a little higher and fitted enough to stay up without a belt- but have the leg styling is a good move. None of your examples have a top that’s tucked-in or highlights the baggy waist, so who’se to know if you’ve got a modified style?

    1. Boyfriend jeans aren’t meant to be worn with a tucked-in top. As for a belt, I highly recommend the Beltaway which is made for this very purpose. Extremely slimline, made in indigo to match the jeans, no metal so it doesn’t have to be removed when going through TSA, I find it helps keep my jeans in place without adding bulk.

      1. Thanks, Allie, for the mention of the Beltaway. So many of my stretch jeans require help to stay up, but, sometimes, I prefer not to have the belt show.

      2. I beg to differ… Actually, boyfriend jeans look pretty cool with tight, tucked-in T-shirts (not blouses), if it`s not the outer layer. Although one should be comfortable with showing the lower tummy area.

        1. Or not even tight. I know it’s 80’s, but Madonna’s “Papa Don’t Preach” video look of a Breton striped tee tucked into belted and cuffed boyfriend jeans with little black ballet flats is still a look I think works beautifully.

        2. Let me rephrase it… if you are worried about your midsection, wearing boyfriend jeans with a blouse tucked in may not be your best choice. But yes, boyfriend jeans with a tucked in top can look pretty fantastic on those who are comfortable with the trend and comfortable with their midsection and comfortable with a very trendy silhouette.

          1. I completely agree. My midsection is bigger than the rest of me, so that look doesn’t work on me because it’s physically uncomfortable, rather than me not wanting to emphasise my waist. I do think it’s a great look on others and would wear it if it didn’t feel like I was being bisected.

  10. Wonderful outfits, Allie! You put pieces together that I would never come up with but are combinations I like. That’s why you (should) get the big bucks. I would, however, have to add some arch supports to the flats and perhaps pick a sandal with a little arch. I have high arches. Wearing completely flat shoes is painful as are any shoes with heels higher than 1 1/2 inches.


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