Cargo pants outfits for women over 50

This post is about cargo pants outfits for women over 50. Learn how and when to partake in this fun fall trend.

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Like everything else Y2K, cargo pants are having a moment again. I should have held onto ALL the things I had back then. But the styles change a bit, the materials are new and I’m different. My body is very different than it was back in the early 2000s pre twins, my husband, and my 50s. 

I need a different kind of cargo pants, not the same ones that I had in my 30s. 

This new again trend is going strong with younger generations. They are sporting half tops, tanks, and lingerie as a shirt with their cargo pants. If you’re into rocking that at school pick-up or your board meeting, I’m in awe.  If you’re more like me and want to wear this style of pants but in a way that feels more comfortable for your mid-life body and lifestyle, then I’ve got some great ideas for you. I found fun ways to wear cargo pants that don’t require bearing your midriff or your undergarments. 

While at the mall the other day I found 3 pairs of cargo pants that I liked and styled a couple of different ways. The styling is what makes these comfortable for me to wear in midlife. I challenged myself to find something in each store I was in that would work with the cargo pants. This limited my options, but that made it more fun. 

What should I wear with cargo pants?

It depends on the style of the cargo pants. At the mall, I found a slim fit, a fuller cut, and a pair that was a little on the lower-rise side. The silhouette of the pants factor into what you should pair with them.

Remember to consider proportions. If you have a fuller pair of pants, try to wear a more fitted top. More fitted pants, then a looser or blousy top will work great. Also, take your body type into consideration when choosing cargo pants. If you carry weight on the bottom, select slimmer profile pants. If you carry weight above your waist, then fuller pants will help balance things out. 

For shoes, you can go in any direction. Tennis shoes for a super casual look. Sandals in the warmer months, heels for a dressier look, or loafers for a more classic touch. 

What type of shirt goes with cargo pants? 

Again it depends on the type of cargo pants. A sweater, oxford shirt, blouse, or a t-shirt are all great options. You can also layer with blazers, a leather jacket, or an oversized cardigan.

Keep in mind the cut of your pants and pair the shirt accordingly. For example a slimmer cut of pants you can pair with a boxy sweater. For a fuller cut of pants, you would want to wear a fitted sweater or shirt. I’ve got some examples below from my shopping trip. 

I paired the straight-leg cargo pants with a cashmere polo sweater, an oversize silk blouse, and a funnel neck cashmere sweater in a similar color for a monochromatic look.

The terracotta-colored cargo pants are more fitted, and despite the slimmer cut, these were incredibly comfortable. It was like wearing sweats or yoga pants. They had a ton of stretch. I would size up. For these pants, I found a boxy oversize turtleneck in a neutral color with a trim of an orange-pink at the cuffs. The second option is a color-blocked sweater with purple and orange. I tucked the boxy sweater to highlight my waist and the color-blocked sweater had a fitted waistband. Be sure to accentuate your waist. 

The last pair of cargo pants are fuller in the hips then taper down at the bottom. These are more like slacks than the other two pairs. The punch of pink was fun with the olive. I like the cardigan alone with this sweater but it would look cute with a tank, cami, or t-shirt under it as well. 

The leopard print silky blouse shows the versatility of these pants to dress up or down. These pants could even go corporate with a silk bow blouse, or something with a subtle pattern. Or date night with a sexier top or low-cut sweater. I was in the Gap so blouse options were limited. 

My favorite option with these pants is the chocolate brown button-up sweater. It’s dark and classic with fun big buttons and a slight puff at the shoulder. 

What color should my cargos be?

The traditional color is an army or olive green. But these come in many colors including denim. So if you have a capsule wardrobe, use the same base color you do for that, or something from your color palette. Neutral gives you more flexibility but if you want to go for a punch of color, cargo pants are a great option. Here are a few in bold colors and patterns. 

If you have a capsule wardrobe, cargo pants is a great option for your black pants. Remember your neutral color can be navy, olive, tan, black. I had a client do pink once. It just has to be neutral enough to work with lots of things in your wardrobe.

Cargo pants outfit ideas

I shared some tops I paired with the different cargo pants above, but here are some complete outfits, shoes, jackets, accessories, and all. This will help give you some ideas for how to wear your cargo pants. 

cream colored collard sweater, gold earrings, olive colored cargo pants, mushroom faux suede sling bag, multi-colored loafers is a perfect cargo pants outfit.
Cashmere sweater/ gold hoop earrings/ sling bag/ olive cargo pants/ chunky loafers

I took the casual vibe of the sweater and pants and added more casual elements for a relaxed look that is easy to wear running errands, to a low-key gathering, casual Friday at the office, or to your kids sport events.

boxy turtleneck sweater, terracotta cargo pants, puffer tote, woven slides
Boxy turtleneck sweater/ squared off hoops/ terracotta cargo pants/ puffer tote/ woven slides

I made this outfit somewhat monochromatic with lots of neutrals and a few touches of color. The pants are kind of bold, so I tried to play the rest of the outfit down.

brown sweater, with olive cargo pants, dangle earrings, woven clutch and sued open toe shoes make a great cargo pants outfit.
Chocolate puff sleeve sweater/ dangle earrings/ olive colored cargo pants/ wine colored woven clutch/ burgundy colored open toe suede heels

This is such a fun date night or girls night out outfit. Full disclosure, I can no longer wear heels like this, but thought they were so pretty that I had to include them here. If can’t do heels right now, a kitten heel or block heel would be great with this. The earrings and sweater styled off-the-shoulder add all the sass you need.

When should I wear these cargo pants outfits

You can wear cargo pants almost anywhere, it’s a matter of what you wear with them. An oxford shirt and loafers make cargo pants work friendly. A silky blouse and heels are perfect for a date night. Cargo pants and a sweater with tennis shoes are great for running errands around town. You can make cargo pants outfits anything you want them to be, just get creative.

Go get your pants on

Cargo pants that is. Now it’s your turn. Grab a pair of cargo pants. Either those you’ve held onto, or grab a new pair and dig around in your closet and see what you’ve got on hand to wear with them. Be creative, try something other than a t-shirt with them and discover how many places you can wear these. It’s a fun fall trend not only for the younger generations but us mid-lifers. It should be easy to wear now that I’ve shown you some grown-up ways to do so. 



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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