Super Comfy Work to Weekend Pants

Ever since mid-August when I headed back to work, I have been diligently searching for a few updated pieces that I can wear to work and on the weekend. Unfortunately, the hunt has proven much harder than I thought because there have been so many summer-y items on display. Although these pieces were all super cute, most of them wouldn’t work for work, weekend and the upcoming cooler temps in Chicago.

The Struggle to Find Work Pants is REAL!

Bottom line: I haven’t had a ton of luck shopping… yet, except for one pair of pants I bought last month that I’m OBSESSED with. Because I’ve been wearing these extremely comfortable and versatile pants all the time I figured I’d share them here on the blog for others who may be struggling to find a versatile pair. I don’t know about you guys, but finding a comfortable pair of work pants (that can be worn on the weekend too) is not as easy as it sounds. That’s why I’m extra excited to report back on this pair.

The Pants and Fit Details

This is the pair of pants I’m talking about. They are straight legged, very soft to touch and have a teeny-tiny bit of stretch. I was a bit nervous that they were “too tight” when I first tried them on, but I’m so glad I stuck with the tighter pair because of the slight stretch. Being 19 weeks pregnant, I have definitely gained some weight since buying them and have still been wearing them on repeat because their stretch is pretty forgiving (without being too much).

My advice to others looking to buy this pair is to buy them in your size and if you teeter between two different sizes, go for the smaller size because of the slight stretch (especially after a few wears). To give you an idea on how much use I actually get out of this pair of pants, I’ve put together three looks. One for work, one for a casual weekend, and one for a night out.

Inspiration for Work

For work, I usually pair these pants with flats, a blouse, sometimes a blazer/sweater, and my work bag. I was slightly nervous about the green color but have quickly learned that this hue is a lot more versatile than I expected it to be.

From blacks to blues and even some patterns (like this non-maternity yet very flattering checkered blouse for $16), the green pants seem to pair well with a lot of the blouses in my closet. I’ve also used Pinterest to search for “green pants outfit inspiration”, which has been extremely helpful in showing me how to pair the green pants with items I already own.

But the great news is that these comfy pants can easily transition into the weekend too.

Inspiration for a Casual Weekend Look

I went with a casual fall outfit for this weekend look by pairing these pants with a long sleeve striped shirt and one of my favorite vests. I went with my converse sneakers since I usually live in these if I’m running errands on the weekend.

Side note: If you’re looking for a go-to striped blouse this fall, I highly recommend this one… for $9!!! It’s more of a polyester blend instead of cotton, which I actually love because it’s lightweight and doesn’t require any ironing. Plus the patchwork elbows are adorable and the midsection is loose (bonus!). And for $9?!

It hasn’t been super chilly here in Chicago just yet, but a colorful scarf could be a great way to make this look even more cozy over the next few months.

But swapping the converse out for some fall booties/wedges and adding a trendier blouse, these versatile pants can easily transition to a fall night out too! They are just so comfortable and worth the investment (especially when they’re on sale) as a fall staple in your closet.

A Night Out Inspiration

When I bought these I never expected to wear them “out”. But Pinterest told me otherwise and I’m so happy I mixed and matched what I already had in my closet to be able to transition these for pants for a night out too.

I paired them with my favorite lace blouse and my go-to leather jacket for this look. It’s super easy, yet very comfy, which is always a win-win in my playbook!

Work to Weekend Pants

I actually love J. Crew Factory for work to weekend pants in general. I bought this pair (in black and blue) last season and still wear them at least once a week to work. Just like the green ones, these have a slight stretch, which makes them super comfy. They also have a higher waist. I love for the classroom since I’m bending, stretching, and sitting on the ground sometimes. The higher the waist = the better!

Overall, all three pairs of work pants get my stamp of approval. I’ve been getting as many uses out of them as possible before my bump is too big! But until then, where do you guys find your favorite work to weekend pants?! I swear hunting for new work pants in one of my least favorite things to shop for so I would love to hear your tried and true favorites.


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The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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