Yeah! I really do feel like we have related styles, so I'm glad that my predictions and descriptors seem right on. And I loooove your pintrest pics, so even better.
WARNING: This is going to be long and rambling.
Here's my take on why it is so hard to translate that into your wardrobe: the type of pieces that you need aren't fast fashion pieces for the most part. They are pieces that have to be picked with care. They are pieces that are going to carry you for years, though. Angie has really opened my eyes about that. The care with which she assembles her wardrobe is inspiring. Your pintrest loves are strong pieces worth investing in.
I don't know about you, but I have a tendency to be a little random in my casual looks. I pick up a piece here, a piece there. Until recently, I never really thought about my casual style in the same way that I thought about my work style. And honestly, the kiddos really took a toll on my style when it came to casual gear. Until recently (as in less than a year recently), the kiddos meant that my casual wear had to stand up to be barfed on and washed in hot water. It still has to stand up to being grabbed with grubby, greasy hands and washed in hot water 90% of the time. And having little ones means you don't have the time to search for the right pieces or even sometimes think about what those right pieces should be! I responded by collecting a mishmash of pieces that all met the "stands up to" criterion, but didn't do much more. I had a closet full of clothes, but nothing to wear. Just isolated pairings, not a wardrobe.
So, I've stepped back and am working on a more disciplined casual wardrobe. I love striped tees, like you, so I have three that fit very very well. All three look great under our avant-garde jacket (Yeah! Jacket twin! Jacket win!). I like jeans for the weekend, so I have several pairs that fit well. I have a sweater gap that I'm struggling with. However, now that I've recognized it, I can shop for it in a disciplined way. Since my wardrobe is for weekends, I only really need one great casual sweater for a season. I have dressier sweaters and dressier tunic tops from work that I can re-purpose for dressier casual at need. I also have several really really great pairs of boots, which are high, low, and mid, and flat and low heeled. I have a great pea coat, military style coat like Angie's and puffer. I have several good leather bags that I've acquired over time and which work well with my casual style, even though they were bought for my dress style. I'm almost there!
When I look at your wardrobe picks on pintrest, I see that you really want to buy a number of things that you should be able to multipurpose for your work style and your casual style. The tailored element makes them so adaptable. Honestly, your pintrest style is so cohesive, I bet you can sit back after you hear what everyone says here and pick out a handful of pieces to buy that will make everything come together. And I can't wait to see it!
PS: Just adding this tidbit. A dark leather jacket or coat is a ridiculously good investment when you have kids. Leather cleans up with wet wipes.