On The Town: Classic Fall in Winter Park

Ashley Brooke Designs _ Lands End


Sweater Weather

In central Florida, we have sweater weather, like, four times a year, and it is GLORIOUS. If you are a Florida native like me, you know what I am talking about; not only do you wait by the Weather Channel and pray that there may possibly be a day in the next 10 day forecast that will fall below 80, but you also have that perfect Fall outfit picked out and ready juuuuust in case it sneaks up on you! To be clear, this is what we wear in Florida when the thermometer hits 75, so if you are visiting, do not be alarmed. We are all just pretending it’s Fall–go with it. 

Like I said, we all have our boots, scarves, and sweaters that are just waiting for that perfect day to be worn, and this, my friends, is my outfit! I love this look so very, very much, plus nothing gets me quite like a cable knit sweater and a pair of riding boots! Also, if you are going to go all out for Fall, you might as well swing by Starbucks and order yourself a “tall-non-fat-1/2 pump -pumpkin-spice-latte” and call it a day! 


Ashley Brooke Designs _ Lands End 4



L.L.Bean Sweater c/o (also love this one), L.L.Bean Scarf c/o, Impecable Pig Jeans, Cuyana short tote, Francesca’s Earrings, Julep Lipstick in “Stepping Out” c/o, Jack Rogers Boots c/o



Ashley Brooke Designs _ Lands End 5


Also, if you are looking for the best coffee date spot of all time, I’ve got you covered! Here is what you need to do: go to Winter Park, park your car on Park Avenue, stop in the Starbucks and pick yourself up a couple of PSLs and walk on over to the Rollins College campus. Not only is it beautiful, but it’s full of little tucked away gems like this one, perfect for a date with your best gal pal or favorite guy! 


Ashley Brooke Designs _ Lands End 3


Ashley Brooke Designs _ Lands End 7


Ashley Brooke Designs _ Lands End 2


Ashley Brooke Designs _ Lands End 6




Photographed by Gregory Daniel

In Partnership with L.L.Bean + Jack Rogers




  1. Marni
    October 7, 2015 / 8:52 am

    I live in CT where it gets REALLY cold ­čśë but this outfit would work here too…just throw on a fabulous leather or corduroy blazer and a cute floppy fedora with some fingerless gloves et voila! Thanks ABD! Love the cute look! Bring on Fall!!!

  2. Rebecca
    October 7, 2015 / 11:26 am

    I would LOOOOOOOOVEEEEE to see a how-to post on your updo here! Pretty Please! ­čÖé

  3. Jessica
    October 7, 2015 / 3:22 pm

    As a fellow Florida gal this is 100000% TRUE! If it’s 75 or below you bet I’m rockin’ boots and a sweater. Cute post! Love!


  4. Lindsey
    October 7, 2015 / 4:44 pm

    This is the exact same thing we do with Autumn in Texas! Love the outfit!

  5. October 13, 2015 / 11:57 pm

    I totally understand what you are talking about. I live in Southern California and it is still so hot! I am dying for a little cooler weather.


  6. Gretchen
    October 24, 2015 / 2:01 pm

    I didn’t know jack rogers had boots I am so getting a pair!!

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