Work to Weekend | Bootcut Jeans

Don’t you just love Thursdays, and the promise they hold? It’s practically Friday, which might as well be the weekend! Or least that’s how I like to spin it. My offices have always had casual Fridays, but even still, I could have gotten away with wearing certain denim during the week, too.

Especially a dark rinse bootcut that fit like a glove. I sang the praises of these jeans in my Blazer & Bootcuts post last month, and I just can’t get enough of them! They are insanely flattering, and so comfortable. Don’t get me wrong, I love my skinny jeans…particularly my distressed ones…but it’s almost a relief to pull on a pair of jeans where nothing pops out!

For today’s style inspiration, I’m wearing my favorite bootcut jeans for both Work and Weekend.

Not only do these jeans hold everything in place, but I can bend over without putting on a crack show! And thanks to the dark rinse, mid-rise, and longer inseam, my legs look a mile long. Okay, okay, that’s a bit of an exaggeration. But I look taller than my actual 5’4″, right?!

When paired with a blouse and classic black pumps, the look is ready for the office. I threw on the statement necklace and leopard belt because I can’t help myself…but if that’s too much for your work environment, the outfit is just as chic without.

Fit Tip: I originally thought these jeans were true-to-size, but after a full wear, I realized you actually need to size down one. I’m wearing a regular 0, and the length is perfect for heels. The petite size was significantly shorter, and ideal for flats. 

Sugarplum Style Tip: Get the most flattering fit out of your bootcut jeans by pairing them with heels, and make sure the hem barely brushes the floor. I prefer a pointy-toe, but as long as your shoe is visible beneath the jeans, you’re good. If you’re more comfortable in flats, stick with a pointy toe (like these), and have the hem brush the top of your foot.

This blouse is a soft mix of knit and rayon, so it drapes beautifully. It’s actually long enough to pair with leggings, but can be tucked in jeans, slacks or a skirt, as well. I also love it with this classic pencil skirt.

Fit Tip: I’m wearing a regular XS in the top. The petite size fit me well, too, but isn’t long enough for leggings.

And as great as a bootcut jean looks for work, it’s even more smashing for a night out! Paired with a simple camisole and some statement jewels, they are date night ready. I’ve worn this exact combination of top and accessories with my skinny jeans and boots, but the bootcut jeans and heels take it to a whole other level.

Camisole Tank (available in 12 colors!)Bootcut Jeans | Necklace | Similar Leopard Pumps
Similar Leather Jacket | ClutchSunglasses | Watch | Link Bracelet | Earrings

Y’all…look at my legs! Keep in mind I’m only 5’4″, and I have a long torso! I’m not what you’d consider leggy. Long legs are not my gift. You get where I’m going with this? There’s magic in these jeans I tell ya! (Mom, these are the ones I was telling you about! Order them in petite, but go down a size. xo)

Camisole Tank (available in 12 colors!) | Bootcut Jeans | Necklace | Similar Leopard Pumps
Similar Leather Jacket | Clutch | Sunglasses | Watch | Link Bracelet | Earrings

I have this tank in three colors…it’s a great layering piece under jackets and blazers, and sassy on it’s own.
Camisole Tank (available in 12 colors!) | Bootcut Jeans 

Camisole Tank (available in 12 colors!) | Necklace 
Camisole Tank (available in 12 colors!) | Bootcut Jeans | Necklace  

Camisole Tank (available in 12 colors!) | Necklace | Similar Leather Jacket | Clutch 

Camisole Tank (available in 12 colors!) | Bootcut Jeans | Necklace | Similar Leopard Pumps
Similar Leather Jacket | Clutch |

Here’s another work wear look featuring the bootcut jeans you may remember from this post

These jeans really go a long way, and somehow manage to make every combination stylish. Have you worn bootcut jeans in awhile? There’s a reason why they keep coming back…they’re pretty much universally flattering! Happy practically the weekend, lovebugs!

{Shop the Work Wear Look}

{Shop the Weekend Look}

Photos by the darling & talented Mary Summers.

*This post is created in collaboration with Nordstrom, but all clothing, style ideas, and daddy longlegs impressions are my own. Thank you for supporting Hi Sugarplum sponsors!*

Leave a Comment


  1. Those jeans are fabulous on you!

    Posted 9.22.16 Reply
  2. MelissaG wrote:

    Cute! I am shocked you can wear those for non Jean days. I have some trouser jeans that look def more like trousers than jeans, but these are clearly jeans! You must have a very relaxed boss!!

    Posted 9.22.16 Reply
    • Yes, I've always worked in more relaxed, creative environments. But I still stick with dark wash and dress them up when sneaking denim during the week! 😉 xo

      Posted 9.22.16 Reply
  3. I MEAN! This is a great post! You look AT LEAST 5'6" in these jeans and you have legs for days!!!!!

    Posted 9.22.16 Reply
  4. I was actually planning to pull some out of my closet today! These look fabulous on you, the colors on that first outfit are way too cute!

    Posted 9.22.16 Reply
  5. Anonymous wrote:

    You look fabulous!! I love all of the looks you created!

    Posted 9.22.16 Reply
  6. Miracle jeans! Skinnies are my go-to, but I like changing it up sometimes and just love how bootcut jeans look with pointy toe heels (and boots). And you look fab, as always 🙂


    Posted 9.22.16 Reply
  7. Hi Cassie,
    Could you please tell me what size you got in the camisole? Thanks!

    Posted 9.22.16 Reply
    • Hi Sherece!! I'm wearing a US4. Topshop runs a little small for me (or rather, euro sizing is prob more accurate!).

      Posted 9.22.16 Reply
  8. Caitlin wrote:

    I love that purple blouse! I will be stealing that outfit look 🙂 I, too, love boot cut jeans – they definitely seem to be the most flattering.

    Posted 9.22.16 Reply
  9. Hi! I love the bracelet on your right wrist in the photos with the jeans, camisole and black jacket but it isn't listed as a link. Do you remember where it was purchased?? LOVE your blog!!

    Posted 9.22.16 Reply
    • Thanks Tara!! It's from Accessory Concierge, but I couldn't find it on their site…mine is pretty old. Here's the link to their site:

      Posted 9.22.16 Reply
  10. Jillian wrote:

    i love that white tank! xo jillian – cornflake dreams

    Posted 9.22.16 Reply
  11. Leigh wrote:

    I just bought those jeans last weekend and I love them so much! I love a bootcut with my body shape and these are perfect.

    Posted 9.22.16 Reply
  12. Callie wrote:

    I love my jeans! But, I agree that I wish I had sized down. Do you think Nordstrom would return after washing? And funny that you are 5'4" and they arent too long. Mine are too long with my good heels. Short legs!

    Posted 9.22.16 Reply
    • I do have to wear them with my tallest heels, or they drag a bit. I'm debating having them hemmed a half-inch. And yes, Nordstrom will totally exchange/return. They are the best…hence why I stick with them so much! xo

      Posted 9.22.16 Reply
  13. Love these jeans! The purplely pink top is so pretty on you!! You look fab!!

    Posted 9.23.16 Reply