Playing Grown Up.

The other day, we had a very high-stakes meeting with an investor we really respect. I’m a huge believer in dressing for confidence — so even though we were meeting at a hipster coffee spot (per usual in the startup scene), I wore a black shift with big gold glossy buttons, Chanel earrings (a sweet gift from my bestie when I was her MOH — RealReal has a great vintage collection you can sort through, including the ones below!), Chanel cap-toe flats ($750 — but check out RealReal for some gently worn styles, like these), a deep red Nars lipstick (Hyde Park, $26), and a fresh-for-fall burgundy nail polish — I really like CND’s week-long polish formula, and went with their Bloodline color, which looks much more red than purple when on ($10). (I was oddly excited to switch from my go-to stark white / bright red to this deep fall color!)

The meeting went well and I attribute it in part to dressing with my a-game in mind. Some other pieces that fit the bill for me:

+RedValentino dress ($695 — love those buttons!);

+These RIDIC burgundy lace-ups give my Aquazzuras a run for their money — and they are affordable at $120! Ladies, snap these up.

+Ruffle-neck top ($60).

+Poncho ($119).

+Chic gray pointed-toe flats in the coolest gray heather from new-to-me line Margaux ($185).

+NPFW (#notpracticalforwork), but I die over this mini Fendi crossbody ($1800).

+Pearl + pom necklace (on sale for $60!)

+Givenchy pouch ($360).

+Stubbs + Wootton loafers ($450).

+I know the high-neck lace collar might seem a little Old Maid, but I think this velvet dress, while a splurge, is as chic as they come ($835). Hair up in a chignon and some great heels (Manolo, $595).

+Still obsessed with the clean lines of this coat ($69).

+Bucket bag ($375).

+My favorite shoe for the season (Prada, $690).

+Tweed peplum jacket ($429, plus 30% off!)

+Layered pearl necklace ($36).

+Elegant bow-front blouse ($185).

+Boucle-trimmed tweed dress ($845).