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Hi Sugarplum!

{5 Ways} Transitioning to Early Fall

September 18, 2015

Oh happy Friday! I’m headed home later today after a fun and inspiring few days in NYC. I had the honor of attending the Better Homes & Gardens Stylemaker Event, with many of my blogger favorites. It’s so exhilarating to be around fellow creatives who love design, fashion, food, travel and blogging as much as I do. I’m full of new ideas and motivation to actually tackle them!

New York City is always exhilarating, but especially gorgeous in the Fall. But just like home (and probably most of the country), Fall is creeping in like a cat…taking her sweet time, with occasional cool mornings, but still warm and sunny days.

It’s true Fall style is all about scarves, boots, jeans, and layers. But what happens when the calendar reads Fall, but the weather says ‘still Summer’?! For today’s {5 Ways}, I thought it’d be fun to share how I ease in to the early days of Fall.

Hi Sugarplum | {5 Ways} Transition to Early Fall

As soon as Fall rolls around, I want to pull out all my favorite cool weather pieces, and wear them all at once (like this Later look). But that’s a heat stroke waiting to happen. So in these early days, I take my usual Summer outfit, and swap in one or two Fall pieces.

ONE |  Jeans and a favorite white tee are season-less…but throw on a lightweight scarf (save the wool plaid for cooler temps!) and boots, and you’re Fall-ready. I opt for a scarf with darker hues when wearing with boots…the idea is a complete Fall look, not Summer on top and Fall on the bottom.

Hi Sugarplum | {5 Ways} Transition to Early Fall
Favorite White Tee | Mid-Rise Distressed Jeans | Leopard Scarf | Knee-High Boots
Slouchy Tote | Bag Tassel Charm | Bamboo Sunglasses
Hi Sugarplum | {5 Ways} Transition to Early Fall
(How to Tie Scarves post here)
Hi Sugarplum | {5 Ways} Transition to Early Fall
Favorite White Tee | Mid-Rise Distressed Jeans | Leopard Scarf | Knee-High Boots
Slouchy Tote | Bag Tassel Charm | Bamboo Sunglasses | Watch | Earrings

Hi Sugarplum | {5 Ways} Transition to Early Fall

TWO |  I follow a similar formula as my How to Transition to Spring…if my legs are bare, then I wear a long-sleeve top, and vice versa with long pants and short-sleeve or sleeveless tops. For the Summer months, I wore this skirt with sleeveless tops and strappy sandals…now I’m swapping to a long-sleeve shirt and substantial shoe for a more season-appropriate look.

Hi Sugarplum | {5 Ways} Transition to Early Fall
Chambray Shirt | Floral Skirt (similar) | Monogrammed Striped Bag
Cage Heels (similar) | Pearl Cluster Necklace
Hi Sugarplum | {5 Ways} Transition to Early Fall

Hi Sugarplum | {5 Ways} Transition to Early Fall
Chambray Shirt | Floral Skirt (similar) | Monogrammed Striped Bag
Cage Heels (similar) | Pearl Cluster Necklace | Earrings | Bracelet | Watch

Hi Sugarplum | {5 Ways} Transition to Early Fall

THREE |  I continue to wear white well past Labor Day (year-round in fact…see my {5 Ways} White Jeans post here), but I do reach for the clothes in heavier fabrics, or add another layer like a jean or military jacket. I prefer a light, neutral boot with white pants for a more seamless flow from leg to foot.

Hi Sugarplum | {5 Ways} Transition to Early Fall
Jean Jacket | Favorite Black Tee | White Jeans (similar) | Leopard Belt 
Low-Ankle Booties | Tassel Pendant Necklace | Black Watch Tote | Sunglasses
Hi Sugarplum | {5 Ways} Transition to Early Fall

Hi Sugarplum | {5 Ways} Transition to Early Fall
Jean Jacket | Favorite Black Tee | White Jeans (similar) | Leopard Belt | Watch
Low-Ankle Booties | Tassel Pendant Necklace | Black Watch Tote | Sunglasses | Bracelet

I shared a few of Barrington’s new fall collection patterns with you in yesterday’s Look for Less post…and this black watch is another winner. I love the classic navy and green combo, and the plaid is perfect for all my Fall and Winter outfits. This bag was my carry-on this week, and I packed it full. You lucky ducks can grab one on sale…any size bag and pattern, use SUGARPLUM10 for 10% your order!

Hi Sugarplum | {5 Ways} Transition to Early Fall

FOUR |  I preach the merits of jean and utility jackets all the time, but sometimes you want something lighter, or dressier. Or with a splash of pattern or color. Well, hello cardigan. I’m took this outfit from Summer to Fall (see the Summer version in NYC here) by simply adding a cardigan layer.

Hi Sugarplum | {5 Ways} Transition to Early Fall
Favorite Black Dress | Striped Drape-front Cardigan | Necklace
Sunglasses | Patent Sandals | Snakeskin Clutch (similar)
Hi Sugarplum | {5 Ways} Transition to Early Fall

Hi Sugarplum | {5 Ways} Transition to Early Fall
Favorite Black Dress | Striped Drape-front Cardigan | Necklace
Sunglasses | Patent Sandals | Snakeskin Clutch (similar) | Cross Bracelet | Earrings

Hi Sugarplum | {5 Ways} Transition to Early Fall

FIVE |  I’m a shorts-girl, and will wear them well past ridiculousness…I especially love pairing them with soft plaids as the days get cooler. You could even swap the sandals for booties, and add a light jacket. Again, for me it’s all about covering my arms or legs, and mixing in a standard Fall piece or two.

Hi Sugarplum | {5 Ways} Transition to Early Fall
Plaid Flannel Shirt | White Cut-Off Shorts | Leopard Sandals
Wooden Bead Necklace | Sunglasses
Hi Sugarplum | {5 Ways} Transition to Early Fall

Hi Sugarplum | {5 Ways} Transition to Early Fall
Plaid Flannel Shirt | White Cut-Off Shorts | Leopard Sandals
Wooden Bead Necklace | Sunglasses | Watch | Earrings | Bracelet | Crossbody Bag

Hi Sugarplum | {5 Ways} Transition to Early Fall

Is Fall creeping up slow in your area, or already there in full-force? I hope this post gave you some new ideas and inspiration for easing in to the new season! I’ll follow up with more transitional looks when Fall truly arrives.


See more {5 Ways} posts here, and keep the requests for more coming! Happy weekend, lovebugs!



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by Cassie 
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Fall & Winter Style, Five Ways

 

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Comments

  1. Sheaffer {Pinterest Told Me To} says: September 18, 2015 at 11:09 am

    I LOVE these posts of yours. Such great tips! My fav look from today's post is definitely the plaid with the white shorts! I think I might frame that 2nd to last pic of you and Maggie and put it on my bedside table.

    Reply
    • hisugarplum says: September 19, 2015 at 3:38 pm

      Great, now what am I going to get you for Christmas?!!? 😉 xo

      Reply
  2. Jillian Manesh says: September 18, 2015 at 11:48 am

    i love all these outfits! i cant wait to start wearing jeans + my jean jacket 🙂 bring on fall!!! xo jillian – stop by! I'm hosting a freshly picked moccasin giveaway on cornflake dreams

    Reply
  3. Ellen Ross | Ask Away says: September 18, 2015 at 1:01 pm

    love what you did with the chambray shirt. thats my favorite thing to do!

    Reply
  4. Caitlin - The Delighted Dwelling says: September 18, 2015 at 1:13 pm

    Love all these looks!! And Maggie is just the cutest!!!

    Reply
  5. the undomesticated wife says: September 18, 2015 at 1:36 pm

    Maggie is so darn cute!

    Reply
  6. Michelle N. says: September 18, 2015 at 2:34 pm

    Gotta echo.. love Maggie!
    I'm in Illinois and I've worn jeans once so far. It got cool the last week of August but then its went right back up to 80s. I can't even think about wearing boots and scarves yet. It would kill me! Thanks for the inspirtation!

    Reply
  7. Judy Clark says: September 18, 2015 at 2:54 pm

    Cassie, I love your blog and your wonderful sense of style. I am a more seasoned gal, but I have been able to modify many of your outfits to work for me. The floral skirt is a bit pricey so maybe you could share something in your looks for less section that would work well for most of your readers. Thanks again.

    Reply
    • hisugarplum says: September 19, 2015 at 3:39 pm

      Thanks Judy! I'm thrilled you find some inspiration here! My skirt is several years old, from J.Crew Factory…I wasn't able to find anything similar except the one I linked. Funny enough, the one I linked is the exact skirt I wore in the Redbook shoot! 🙂 xo

      Reply
  8. Queen In Between says: September 18, 2015 at 3:22 pm

    I seriously wore my black dress yesterday with a boyfriend cardi and that EXACT necklace! I love the halogen t-shirt but am curious if you size down.

    Reply
    • hisugarplum says: September 19, 2015 at 3:40 pm

      Cutie!!! I wear a regular XS in the tee…it's the perfect amount of relaxed, without looking slouchy. It washes and dries well, too!

      Reply
  9. Liz Jo says: September 18, 2015 at 8:51 pm

    Love all of your outfits 🙂

    liz jo @ sundays with sophie

    Reply
  10. Mix and Match Mama says: September 19, 2015 at 11:19 am

    I need that flannel shirt! Like really, really need it!

    Reply
  11. Unknown says: September 19, 2015 at 1:40 pm

    #1 and #4 are my personal favorites. Those are the ones I would wear, but quite frankly you pull all five off marvelously 🙂 Happy fall from Oklahoma!!

    Reply
    • hisugarplum says: September 19, 2015 at 3:40 pm

      Thank you, sweet Okie!! 😉 xo

      Reply
  12. Tracy Miller says: September 19, 2015 at 6:36 pm

    Cassie, I found your blog because of your Redbook feature. I can't believe I didn't find you sooner. I am over 40 and sometimes it is hard to find good inspiration for "mom" style. Your asthetic is so similar to mine and I've already pinned many of your outfits. And your home decor posts are excellent too.

    Reply
    • hisugarplum says: September 21, 2015 at 1:23 am

      Tracy…thank you so much! I'm thrilled you found me and hope you get a little inspiration here! The Redbook experience was mind-blowing, that's for sure! xoxo

      Reply
  13. The Freemans says: September 20, 2015 at 2:07 am

    Love, love, love your style! What size white T-shirt do you wear? I've been looking for a good white t-shirt for a while and this one looks great! Just want to order the right size!

    Reply
  14. hisugarplum says: September 21, 2015 at 1:22 am

    Thanks, girlie!! I'm wearing an XS Regular. It's just slouchy enough without being sloppy. And it washes/dries well! xo

    Reply

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