Cheers to Friday! How was your week? Ours was pretty standard, and happily we’re all starting to relax into the new school schedule. Little Miss is so excited to head-out for the big 5th grade camp next week, with me as a chaperone, so we’ll be prepping the sleeping bags and other gear this weekend…along with trying to figure out how to smuggle in a box fan! #notacamper
Today I’m sharing some Now and Later style inspiration…taking one of my favorite t-shirt dresses, and styling it for both warmer days, and later when it (hopefully) starts to cool.

This dress is so easy to wear, and even though it feels like pajamas, it still manages to look pulled together. (This crewneck version is similar, and this one has a fun criss-cross front for the younger crowd.) I’ve been wearing them (I say ‘them’, because I have it in three colors! #oops) all Summer with wedges, flat sandals, and my favorite sneakers (size down one in the Shoreline)….and usually a tassel necklace. Because, tassel. (Find some of my favorites here.)




For cooler nights, or basically every restaurant in town, I add the trusty jean jacket for a light layer of warmth.




Once it cools down even further (or the calendar says ‘Fall’), I’ll swap the sandals for booties, and, if necessary, add one of my Fall’s Essential Seven…a utility jacket. (I might need to revisit this list, but it’s certainly a good start!)
Sugarplum Style Tip: Black booties would work, too, but a more neutral color creates a longer leg-line when wearing boots with dresses.








*This post is created in collaboration with Nordstrom, but all clothes, styling ideas, and boot-scooting are my own. Thank you for supporting sponsors that keep Hi Sugarplum running!*