Plaid Shirtdress | Now & Later

Wow, sounds like ya’ll are as big of a sucker for a good love story and wedding as I am! I’m thrilled you enjoyed yesterday’s post about my sister’s Montana River Wedding, and thank you for your kind comments. I made sure to pass them along to her…and my former stepmom, who helped plan the shindig. 
Well, the calendar may say October, but we’ve still yet to see any real Fall weather. Which totally bites when you have cute new plaids and scarves to wear!


Transitioning our wardrobes to a new season always seems to cause some anxiety, so today I’m sharing another Now & Later…this time around this darling plaid shirtdress, and at Dallas’s prettiest spot to experience the seasons…the Arboretum.
Hi Sugarplum | Plaid Shirtdress / Now & Later

Many dresses can be worn year-round, and I simply swap sandals for booties. But the material of this dress is light enough for warm days, but the color and pattern combination is clearly Fall-specific (so I would put it away during the Summer months)

Boots can look clunky and heavy when worn with a dress, so I prefer a neutral color and streamlined shape for a more flattering look.
Hi Sugarplum | Plaid Shirtdress / Now & Later
Plaid Dress | Crossbody Bag (similar here & here) | Booties
Beaded Necklace | Sunglasses
Clearly these low-ankle booties are favorites of mine this season, since I’ve reached for them almost every Fall Style post (see them all here)! You’ve seen this bag several times already too, and unfortunately it keeps selling out. Don’t you hate when bloggers show things that aren’t available?!? But as much as I’d like to, I can’t exactly buy a new one every time. I did find some really great similar options though. 
Fit Tip: These booties run true-to-size, but require an extra-low sock (I wear these) to avoid peeking out. 
Hi Sugarplum | Plaid Shirtdress / Now & Later
Crossbody Bag (similar here & here) | Booties | Leopard Cuff | Watch | Spike Bracelet
I added the leopard cuff for a touch of pattern-mixing, and that whole Rule of Three thing.
Hi Sugarplum | Plaid Shirtdress / Now & Later
Fit Tip: The dress is women’s sizing, and true to size. I’m wearing an XS.
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later
I love the Dallas Arboretum any time of year, but Fall is nothing short of extraordinary, with over 75,000 pumpkins, hay bale mazes, and concerts in the park. And as we discovered, very well-endowed male squirrels. #bignads #donttouchthatsquirrelsnuts #namethatmovie
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later
Plaid Dress | Crossbody Bag (similar here & here) | Booties
Beaded Necklace | Sunglasses
Now let’s fast forward 30-degrees, and style the same dress for cooler days by layering a vest and scarf. Swapping knee-boots for the booties added some warmth, too.
Style Tip: Try tone-on-tone layers for subtle pattern and texture. Keeping them all the same shade allowed the plaid to remain the star.
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later
Style Tip: I frequently hear the comment, ‘I wish I could get away with wearing a hat!’ You want my advice for that? Just wear the hat! All anyone needs to pull it off, is the confidence to wear it. I prefer the brim be twice the width of my face…no wider, no smaller.
Hi Sugarplum | Plaid Shirtdress / Now & Later
And when it cools down even more, I’ll add an additional jacket layer. I guess these posts should technically be called Now & Later & Even Later. But that doesn’t have the same ring to it. 
Hi Sugarplum | Plaid Shirtdress / Now & Later
Military Jacket (similar) | Plaid Dress | Puffer Vest | Pendant Necklace | Hat (similar)
Boots (similar) | Bag (similar under $50) | Leopard Cuff | Watch | Spike Bracelet
Hi Sugarplum | Plaid Shirtdress / Now & Later
Military Jacket (similar) | Watch | Spike Bracelet
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later
Hi Sugarplum | Plaid Shirtdress / Now & Later

This last pic was another squirrel-spotting reaction. Yes, I’m essentially a 14-year old boy.

And once again, I teetered perilously close to heatstroke shooting these looks for you, so I hope you found some new Fall inspiration! Make sure you come back tomorrow…we’ve got Week 2 of the One Room Challenge to recap. Also known as, a major hiccup.
Thank you, Mary Summers, for the fabulous pictures, and Bailey at The Dallas Arboretum for a fun afternoon!


{Shop More Plaid Shirtdresses}


Leave a Comment

25 Comments

  1. THIS POST IS FABULOUS!!!! You look AMAZING, and the pictures are gorgeous!!!!!

    Posted 10.13.15 Reply
  2. Cassie,
    I actually love the green jacket layered over the plaid. Sorry it was so hot out when you were preparing these looks. I remember doing that for my daughter's youtube channel. She would always be out there in weird weather with different style clothes on.
    Jenn

    Posted 10.13.15 Reply
  3. Christina wrote:

    So cute! Hats do look great on you! I'm not sure I can wear one because of my curly hair. Im afraid it would be a full day commitment. Lol Maaaaybe I'll try one sometime and see if I can prove myself wrong.

    Posted 10.13.15 Reply
  4. i love those boots! and outfits like these make me pretty excited for another winter in the south! xo jillian – cornflake dreams

    Posted 10.13.15 Reply
  5. Just when I think you can't get any cuter you pull off adorable pix like this….and just when I think you could not be any funnier…#bignads…I almost spit my coffee. Love this look and all the layers….totally feel ya on the heat stroke. I hope Texas gets the memo soon!!

    Posted 10.13.15 Reply
  6. I live in Michigan so need to wear some tights under. Would you wear black or another color? Thanks 🙂

    Posted 10.13.15 Reply
    • Hi Kaylyn! With this exact dress, I'd probably wear navy or black. I pretty much stick with dark colors when it comes to tights, but then keep my shoes similar in color to the tights, too. As the weather cools here, I'll add more wintery styles…but we're still at 90-degrees, so there's no way I could muster up tights right now! 🙂

      Posted 10.13.15 Reply
  7. I just cannot get over these pictures! Between today's post and yesterday's…you're killing me with fabulousness!

    Posted 10.13.15 Reply
  8. Momma wrote:

    I would so pair this dress with some black leggings and Tieks…that's just my thing, though…loved you in the boots! I have super skinny bird legs and boots of any kind look a little clunky on me! Btw…#donttouchthatsquirrelsnuts #namethatmovie…Charlie and the Chocolate Factory! One of my kids' favorite!

    Posted 10.13.15 Reply
  9. These pictures came out too cute Cassie! Love them all! xoxo

    Posted 10.13.15 Reply
  10. Adorable! All of it!

    Visiting from LorimerLiving.Com
    XO, Jaclyn

    Posted 10.13.15 Reply
  11. Paula R wrote:

    I looove a plaid shirtdress…and I love these looks you put together with one! I know you posted a link with similar style boots but can you share what brand are the ones you're wearing? I swoon over them every time you have a post with them!

    Posted 10.13.15 Reply
    • Thanks Paula!! My boots are several years old…I'm a big fan of the brand, Franco Sarto. xo

      Posted 10.13.15 Reply
  12. bree west wrote:

    Love this dress! you look gorgeous in all these shots!

    xo Bree
    http://bree-west.com

    Posted 10.13.15 Reply
  13. These are the cutest photos ever! You look darling.

    Posted 10.13.15 Reply
  14. I LOVE these looks! I have the same jacket and I love how you tied the front waist ties so they weren't all dangling down…great idea, will have to steal that:) Thanks for all of your tips!

    Posted 10.13.15 Reply
    • Yay! Glad you found a new tip today!! I adore that jacket! xo

      Posted 10.13.15 Reply
  15. Adorable! As per your usual. Love this blog and enjoy your pics.

    Posted 10.13.15 Reply
  16. diana wrote:

    I have that exact ON vest but can't decide how much I'll wear it with it being off white instead of real white. Does that bother you?

    Posted 10.14.15 Reply
    • I wear mine the same as I would white..it's just a softer hue, not as brash. Perfect for Falll and Winter!! xo

      Posted 10.14.15 Reply
  17. I'm ALL about plaid this year! I can't stop buying it. Thanks for showing so many ways to wear it – I can't wait to try them all out!

    http://www.ingoodcoblog.com

    Posted 10.14.15 Reply
  18. Love that dress and all the styling!

    Posted 10.14.15 Reply
  19. mwimp wrote:

    do u have the info for that exact bag? I luv the stitching and rollover handle detail. I don't like when purses have an edge that is just a covering – it peels after a bit. so I like when they have a rolled edge. Thanks!

    Posted 10.16.15 Reply
  20. I received this dress in the mail today! Love it!!!!! But…..im super long waisted so it's too short to pull off….leggings and boots???????

    Posted 10.17.15 Reply
    • Lucky girl…so tall!! Yes, you could totally wear it as a tunic! It'd be darling with legggings and knee boots, or skinny jeans and ankle boots!! xo

      Posted 10.19.15 Reply