I'm a millennial indie music snob from New England so this combo is extremely my vibe, especially in the summer. J Crew, Madewell, Gap, and Banana Republic all do come to mind for this vibe. They all have tons of stock and inconsistent sizing so you may want to do some try ons before giving up. I would add Sezane and Everlane to this list. My basics are mostly Everlane and Gap these days. Don't sleep on Gap Factory, their pants are tailored a little different and very postpartum/hips friendly for me. Jenni Kayne for the coastal grandma vibes for sure, it's much more expensive but you can look on Poshmark for gently used pieces. I don't love Quince across the board but their cotton and ribbed/chunky cashmere sweaters are terrific Jenni Kayne dupes. Maybe Kule for striped tops as well, their pricy but always have a bulk discount, and they last forever. Clare V for the same with more humor, akd accessories. Some niche European knitwear companies might be of interest too, like Babaa (their thanksgiving and January sales rock!!), Nonna Lietta, or Jaggery London are some I like. I would buy new from these brands as you don't get much of a discount second hand and how they are cared for REALLY matters. I do actually live in my Babaa in the winter (that's their tag line). And of course, Eileen Fisher! Also a good brand to shop second hand. I find even their NYC stores friendly with actually knowledgeable staff to help you try stuff on. More on reddit.com

Super casual with expensive shoes.

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Money talks, wealth whispers. More on reddit.com

There was just a post on r/femalefashionadvice about how Lili in Gossip Girl still looks fashionable because her ‘old money’ aesthetics are always flattering, polished and fashionable, while not necessarily being ‘trendy’. The others in the show are very fashion-forward trend-setting/following and their outfits look very dated now. ‘Old-money’ fashion doesn’t change all that much through time while trends are constantly shifting. I think it’s just about looking effortlessly put-together, which is always a look people are after. Maybe it’s becoming more popular due to a bit of influence from people moving away from fast-fashion and towards quality clothing that lasts. Buying fewer pieces but making what they do buy more special. Of course, I’m sure there are people who will just take it to be ‘rich-looking’ but that’s literally always been trendy in fashion with people wanting brand names all over them and status-symbol pieces. More on reddit.com