How to wear boyfriend jeans over 50

This posts will show you how to wear boyfriend jeans when you’re over 50.

Photo courtesy of Oliver Logan

Bathing suits and jeans. 

My two least favorite things to shop for.

Why is it so hard? The fashion industry insists that we should all fit into specific styles, cuts, and silhouettes that don’t work for the majority of people. Why???

At least the bathing suit thing only comes around once per year. But the jeans, this is a year-round issue, they are part of my capsule wardrobe and something I wear a lot. 

I’ve finally found a silhouette of jeans that works for me:

 Boyfriend Jeans. 

I’ve been coming back to them time and again. The relaxed cut on these doesn’t overwhelm my frame. It still shows my shape but isn’t skin tight. I feel stylish and confident in them.

They are an easy transition back into hard pants post-pandemic and are forgiving of any extra of you that may be around for others to love. And, they feel appropriate to wear as a 50+-year-old woman.

That’s right I’m 50+ now, and digging it, and my boyfriend jeans. So I’m debunking some myths today and sharing with you the ways I love to wear this silhouette. 

What exactly is a boyfriend jean? 

This is a cut of jeans that fits at the waist and hips but is looser in the legs and tapers down at the bottom where they are usually cuffed. They are designed to look worn in men’s jeans that you borrowed from your boyfriend. The loose fit makes them an ideal segue back into real pants after two years of sweats and leggings. 

What’s the difference between mom and boyfriend jeans?

Mom Jeans are baggy all over, especially in the waist. Boyfriend jeans fit in the waist and rear and are looser in the legs and crotch areas. 

Can women over 50 wear boyfriend jeans?

Absolutely! This is a great style for women over 50. They are fitted to show some shape but looser in the legs so it’s comfortable, not so constraining. They offer a polished look and there are tons of options for how to style them.

How to wear boyfriend jeans in your 50s

There are some rules for wearing boyfriend jeans. The only one that matters in my opinion is to pair them with a top that is more fitted, not tight. Because the legs are looser, you don’t want to overwhelm your shape with too much volume up top. I’ve provided a handful of ideas for how to style your boyfriend jeans below. These options are for anyone who wants to look effortlessly pulled together, no matter your age. 

A day around town

Frilly eyelet blouse paired with boyfriend jeans, a bold yellow sandal and striped raffia bag. How to wear boyfriend jeans over 50 is simple follow these outfit templates.

An eyelet top with ruffles adds a feminine and fun touch to these jeans. To balance out the girly vibe, I added metal earrings with straight edges, bold, bright colored shoes and a multi-colored striped purse. These harder edged items tone down the girl vibe and make this a very modern outfit. The color of the shoes ties in nicely with the purse, which is the statement piece of this outfit.

A sweater set is a perfect match with boyfriend jeans. What 50+ year old women doesn’t love a good sweater set? This one has a pink knit tank with a camel and pink color-block cardigan. Add a multi-shade of pink straw bag, these bold fuchsia slides with a flower and another shade of pink sunglasses. Lots of pink in different shades all tied together with the bag. This is a fun look for running errands, grabbing lunch with a friend or shopping at the mall.

Casual day at the office

Green floral blouse with a white fitted blazer, neutral colored loafer and bag make for a great casual day at the office. This is a great outfit idea for women over 50 who want to wear boyfriend jeans.

To wear a blouse with boyfriend jeans is it has to be fitted, not too much extra material. This floral blouse is a perfect pairing with boyfriend jeans. Add a white blazer for a more polished look. The floral earrings tie in nicely with the blouse adding more feminine touches and the neutral shoes and bag add a professional vibe for the office.

A striped oxford, white tote or floral clutch, pearl hoop earrings and pink loafers make a great casual day at the office. This is a great way to wear boyfriend jeans over 50.

This is another possible casual day at the office look. A fitted oxford shirt, love the stripes on this one, with the boyfriend jeans is a way to dress up the casual silhouette. Paired with a classic pearl hoop earring, pink loafers and a natural colored tote, you are ready to power through your day, in style. I love the floral clutch with this look as well, so I left it in there. It could be a take away when you dash out to lunch or your main bag. It depends on how much stuff you need to lug around. I’m a total sucker for stripes and floral paired together.

Vacation at home in your boyfriend jeans

How to wear boyfriend jeans over 50 is to make it your own. Green linen sleeveless, ruffled blouse, green and blue striped raffia bag, blue wedge slides, gold hoops and textured white bracelet make a great vacation outfit.

This summery look would be great to wear on vacation, or on a day when you wish you were away. The sleeveless ruffle linen shirt is fitted, but not tight, so it works with boyfriend jeans. The bold blue shoes are a great contrast to the green and the colored stripes on the straw bag tie it all together. Pair with a fun bracelet or two like this white textured one and simple earrings for an effortless vacation look.

Date night outfit

black silk top, boyfriend jeans, pink feather earrings, rainbow clutch with fuchsia closure and hot pink beaded slides make an appropriate outfit for someone over 50 to wear.

Date night outfits are the hardest for me to come up with these days. What I love about this one is, all of these items can be used for other purposes in my wardrobe. The black silk blouse would be great with a pair of slacks for work, too. Paired with the boyfriend jeans makes the look edgier. Adding in a colorful clutch, I picked up on the pink tones in the bag for my accessories with big pink feather earrings and beaded fuchsia heeled slides.

How to wear boyfriend jeans over 50 is not as hard as it seems. All of these outfits are age appropriate (whatever that means), stylish and polished. Go see if you can piece together a similar outfit in your closet. Play, add pieces that seem out of the ordinary and make it your own.

Let me know in the comments which outfit you’re going to recreate.





I show women over 50 how to get noticed, stay relevant, and be connected through their wardrobe. Getting dressed is something you have to do each day, why not make it fun.



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