the fall clothing transition

TheFallClothingTransitionWhen I think of the summer to fall transition, my mind naturally goes to the most important decision of all: when to switch from drinking iced tea to coffee?

This is an important decision because once I switch, I don’t go back. And if the temps hop around too much, I might end up wishing I’d stuck with my iced tea habit just a little bit longer.

Oh, and then there is the clothing transition. Thankfully, that transition is much easier than the caffeine swap.

When it comes to clothing, I get most excited to wear my jeans and boots once the weather drops. This year, I decided to try the little brown bootie trend.


This is a style that I know is here to stay — at least this season and probably next fall. So I figured I’d test the waters with these reasonably priced guys.

I like that they are the perfect shade of cognac brown and are basically the bootie version of the riding boot. Since I’m new to this trend, I want to keep things as simple as possible to start.

Oh, and you might notice that I cut my hair, too.

HairCutMy hair stylist suggested that I go for the Alexa Chung look. Though I do like the shorter length, I’m still getting used to styling it properly.

Yesterday I tried the Curly Girl method, straightened it immediately after, and then used a curling iron to get more movement… it is definitely still a work in progress.

On the clothing front, as the temperatures keep jumping up and down, I have been pulling clothing from my summer wardrobe into the fall.


During the transition into the fall, I love how the booties pair with white jeans. I think the combo would also look awesome with an oversized gray or navy sweater, too.

And hey, when things start to get chilly, scarves add color and pattern to even the simplest of outfits.


Here’s to the fall! What is your most important “fall transition decision?”


This post is sponsored by Pickwick & Weller (c/o the cozy peach shirt and white slouchy tee) – and they are giving 25% off to JessLively readers! Click here to get the discount on their (really well made) tees. 

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  1. Valerie

    Your hair looks amazing! I wish I could pull something like that, but from past experience, it’s best for me to stick to longer hair (I have a very round face, haha). Love that scarf, and I think I need to invest in a pair of rich chesnut booties like that!

  2. Jennifer

    Your hair looks great!! I think you did a great job styling it 🙂 I’m also really into the bootie look.

  3. Jess Lively

    Thank you so much! I’m still getting used to it. I go back and forth on whether I like it… depends on the day/curl. ; )

    And yes, I’m liking the booties so far. I recommend them.

  4. Jess Lively

    Nice! I am going to look into the Minger polish, I’ve been looking for a new color this fall. : )

  5. arin

    you nailed this look! obsessed with scarves — and love the hair and accessories! hope we can meet soon! chicago gals! Heart of Chic — Don’t forget to enter my giveaway! 🙂

  6. Joy Laforme

    Loving the ‘fall uniform’. Jeans + tees + scarves are a total go-to for me, so I am loving this look. You look amazing with your hair that length! I cut my hair the exact same length back in March and had the hardest time figuring out what to do, so totally get it. Bumble and Bumble surf spray became my best friend. 🙂

      1. Joy Laforme

        I air dry it most days! I curled it if I wanted a more refined look for going out.

        1. Jess Lively

          Nice! Do you have wavy, straight, or curly hair naturally? (I’m curly, but I get keratin).

          1. Joy Laforme

            I have wavy hair – so I try to embrace the frizz/wave on most days, haha!

          2. Jess Lively

            Gotcha. I just heard about the Curly Girl method/book from someone at a wedding. It apparently works wonders on frizz and waves, too.

  7. Susan Berkelbach

    I love the black adn white long sleeve blouse, Where did you get it?

  8. Lauren Malmquist

    Beautiful post! I love the outfits, and your new hair.

  9. Kay

    Cute looks? Is that scarf from j.crew? Also, any tips (or pinterest links!) on how to tie it that way? It looks easy and chic like that 🙂

  10. Sage Grayson

    Fall is an excuse for me to add to my ever-increasing scarf collection. They look great layered with jackets or on their own.

  11. Becca Divine

    Love the hair cut! I wish the fall weather would come a little further south to Texas 🙁 It will be more like November until I can even think about wearing a cute scarf like yours!

    1. Jess Lively

      Thanks, Becca!

      I can imagine it would take a while to cool in Texas. What are the temps like lately?

      1. Becca Divine

        Oh still in the 90s and humid!

  12. Yasmine

    I always lovelovelove your style posts, Jess! Your outfits here look rocking, and your hair looks gorgeous — I wish I had waves or curls, but my hair is pin-straight =/ the grass is always greener!

    So funny that you mentioned white jeans in your post — I bought my first pair of cropped white skinny jeans this summer, but then somehow promptly forgot all about them (I think they got lost in my laundry pile… Oops). I found them again last week, and decided I don’t care about the supposed “no white after Labor Day” rule — I plan to wear the white jeans all through fall and winter and forever! In fact, I’m wearing them today with a peach&pink tshirt, beige blazer, nude heels, and pink/red headwrap. Fall style will just be a continuation of summer style, but with more layers! (HUGE FAN of scarves here, and it helps that the San Francisco Bay Area is always chilly in the morning and evenings — we’re all about layers!)

    1. Jess Lively

      Thanks, Yasmine! So it sounds like you’d like a bit more style every now and then, eh?

      Your outfit today sounds wonderful. If we could, I’d swap looks with you. : )

  13. Jennifer

    Live your hair à la alexa chung!

    1. Jess Lively

      Thank you! There is still an adjustment period, but I’m slowly figuring it out : )

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