Now & Later | Striped Swing Dress

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.)

Jean JacketTassel Necklace (on sale!) 
Saddlebag (more colors here) | Wedges 

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

Dress (similar) | Jean Jacket | Tassel Necklace (on sale!) Wedges | Sunglasses 
Hoop Earrings | Saddlebag (more colors here
Saddlebag (more colors here) | Watch | Link Bracelet

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 Sevena 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.

Pendant Necklace | ClutchSunglasses | Hoop Earrings

Fit Tip: This is a great utility jacket, but runs large…size down!

Mr. SP getting artistic with the camera! 😉
Fall in Texas creeps in slowly, but I love the opportunity it gives to continue wearing my favorite Summer dresses. What’s your favorite way to transition your outfits from Summer to Fall? As much as I love Summer, I love that we’re inching closer to boots and scarves season! I’ll be reaching for this scarf first! Happy weekend, lovebugs!
More Fall Style Inspiration:

{More Transitional Dresses}

{Shop My Outfits}

*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!*

Leave a Comment


  1. Girl! You styled that dress so cute! I think you could wear it five days in a row and no one would even notice due to those accessories. Super cute!

    Posted 9.9.16 Reply
  2. Christina wrote:

    So stinkin' cute! These transitioning to a new season post might be my favorite since Texas is basically Summer, winter or long transitions! Ha! Happy Weekend!

    Posted 9.9.16 Reply
  3. Classy and comfortable.

    Posted 9.9.16 Reply
  4. Love the now + later post! Seriously crushing on those VInce Camuto cutout booties.

    Posted 9.9.16 Reply
  5. I really like seeing how people style one piece for two different seasons. The tassel necklace is super cute!

    Posted 9.9.16 Reply
  6. Anonymous wrote:

    I love these posts so much! It really helps me get the most out of the items in my wardrobe. Thank you so much!

    Posted 9.9.16 Reply
  7. Adorbs! Have fun at camp. You're very brave. 🙂

    Posted 9.9.16 Reply
  8. Love the looks! Your parent driving tunes video on IG cracked me up!

    Posted 9.10.16 Reply