Cute Date Night outfit. Make the jeggings leggings, wear a longer, tunic style jacket, add walkable boots and I love this - I also found a pea coat in almost the exact same red/black plaid as that purse at.
Stitch Fix Stylist - I really like the vintage lace cardigan with floral tank top. It's very feminine. I would probably need a smaller floral print though on my small frame. Not really a fan of the purse as it doesn't look practical with 2 under 2 kids.