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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  • LOVE these outfits, the green pants are awesome. I bought a similar pair of (darker) green pants from J Crew last year, kind of a skinny cargo pant style with an ankle zipper. I love them and wear them all the time casually, you have inspired me to dress them up a bit the next time I go out! That shirt with the elbow patch is adorable, I have it in my shopping cart. I wasn’t torn about size, is it a loose fit? I like my tops more on the flowy side…I have a major thing for elbow patches!

    • I was the same exact way — I had no idea that the green pants could work for a night out either! Love them even more now. =)

      I bought a small (because of the bump, usually I would probably go XS) and so far it’s hiding the bump. I wouldn’t call it super “flowy” but defintely loose around the mid section so it doesn’t hug the torso. I hope that helps!! Plus I figured if it was a tad too tight around the middle (or becomes too tight), I could always wear it with layers/vests and still love it.

  • shawnna griffin

    hey girl- love the pants! so cool!

  • Colleen Berry

    Love these outfits! What color stripe is your striped shirt? I couldn’t tell if it was black or navy.

    • Colleen Berry

      Also what is your feedback on Shein? The prices are amazing, but makes me a little nervous on the quality of the clothing.

    • Yea, I definitely consider the quality before I buy BUT I also remind myself that I’m spending ten bucks so I know it’s not going to be amazing. But surprisingly, I’ve loved everything I have bought from them. I usually make sure to read the reviews and look at the pictures people post wearing the item, because usually i can tell from those real life pics if each piece will fit my body type. Overall, I’m super happy… especially for the price! But do note that the shirts I have bought aren’t typically cotton but more so polyester. I love that (no ironing!) but just something to be aware of before shopping.

    • The stripes are black on the elbow patch shirt. The checkered shirt I can’t really tell. I originally thought navy but have worn it with black pants, and it seems to show black then? So weird but I love it because I wear it with “navy outfits” and “black outfits” and it seems to work!

  • Holly Gordon

    Oh my gosh girl, you have to try Maurice’s! They have a line of skinny pants just like that, in tons of different colors, they’re soft and slightly stretchy, and the best part is they’re regular price is only 34 or 39!
    The only downside is their sizing, you may be, currently, too small. I’m a size 8/10 and I wear a medium.

    • THANK YOU, this sounds amazing!! Unfortauntely we don’t have a ton of Maurice’s in this area but next time I run across one, I’m defintely trying on pants. Love this tip!! Thanks again Holly.

  • Kelly

    Hi Bridget, I love the navy purse in the first 2 photos…do you remember where it is from…..

    • Thanks Kelly! I actually bought it from Marshall’s a while back and use it everyday as my work bag. The brand is Tulio.

  • I LOVE olive pants for fall/winter! I have some very similarly colored ones from Old Navy that have held up really well! Although I’ve never paired them with a vest…I don’t know why!