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!


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