How to wear your dress pants casually

This post shows you how to wear your dress pants in a casual way. Making them a more useful item in your closet.

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“Hey, I had that hole in your pants fixed at the dry cleaners.”

“What hole? There was a hole in my pants?”

“Yes, right up the back seam of the pants. It was pretty big. You didn’t notice it?”

“No, in fact, I did an all-day training in those last week. Bending over to help trainees and revealing I don’t know what to the people in the row behind me! I can’t believe no one told me.”

“It’s kinda hard to bring something like that up during a training session. That you’re leading.”  

This was a conversation I had with a friend whose pants I borrowed for a fancy dinner event I was attending. This was way back when I used to wear slacks, trousers, dress pants (whatever you like to call them) all the time. Even to non-work events.

What to do with all of your corporate slacks

I don’t have a corporate job anymore, but I do have a few pairs of slacks that I’ve been trying to play with to make them wearable for my lifestyle now. Which is way more casual than it used to be. 

Do you too have a stash of beautiful, but seemingly useless, dress pants that you’ve been wondering how to wear casually? I found some easy ways to do so and thought I’d share them with you.

Some examples are from my closet and some finds from the world wide web. No matter what, I’m sure these are casual dress pants outfits you can replicate with little effort. 

How to wear dress pants casually. 

Size up. Wear your pants baggy for a fun take on this classic work staple. This is also a big trend right now. Order pants larger, or opt for a pair that are designed to be baggy.


Wear casual footwear. This is the easiest one. Pair them with sneakers, sandals, or slides. The trick here is you have to wear a less formal top or jacket as well. This is to avoid looking like a city slicker wearing comfy shoes for your walk to work, knowing you’ve got heels stashed in your cubicle. 

Give the pants a vacation vibe. To do this, tie a white shirt, throw on a chunky necklace and some sandals. Something you might wear at a resort. Using two work-wear staples from your closet, you can create a relaxed look.


Add a casual jacket. By throwing on a denim jacket, a sporty puffy coat, leather/suede jacket, or a comfy cardigan with your dress pants for a more casual look.

More ways to make your dress pants casual

Buy dress pants in a bold fun color. You probably have a black, navy, perhaps a pinstripe but what about a pink pinstripe? Kelly green slacks? Try a color that you wouldn’t normally choose in dress pants to make them more approachable for everyday wear and automatically more casual. This is also a great way to partake in the dopamine dressing trend I discussed a while back. Add a few of the other suggestions here to guarantee a casual look for your dressy colorful slacks. 

Monochromatic styling. Wear the same color shirt as pants for a dressed-down look. This would be fun to do in bold color as well. Head to toe pink, bright blue, green, or all white.  

Grab a fun purse. If you’re wearing a classic blue or black pair of slacks, add a heavily patterned clutch, or brightly colored bag to dress down the slacks. This is an easy and inexpensive way to make your dress pants fun, current, and casual.

Add a t-shirt. Plain, striped, or graphic, this will tone down the corporate look of your dress pants. Edgy earrings or a necklace will dress the outfit down further. Throw on your sneakers and you’ll be all set. 

Now it’s your turn. Head to your closet and dig out those dress pants that you most likely haven’t touched in the past two years. Pull them out and start playing. Pick an idea or two from this post and see what you can replicate. You can get those work pants back to work, expand your wardrobe choices, and get more milage out of a clothing item.

Let me know in the comments, which option will you try for wearing your dress pants casually?





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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