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It’s October! I’m so happy for the chillier air. As soon as the temperature fell below 65 I texted Vanessa of East End Taste (Instagram) to ask if she was up for some pumpkin and apple picking in Bridgehampton. She was! We took advantage of the perfect Fall weather so I could shoot these 5 perfect pumpkin or apple picking outfits.
We visited two of my favorite farms, Fairview Farm at Mecox and Milk Pail U-Pick Farm just across Horsemill Lane. If you find yourself out in the Hamptons both of these farms are wonderful! Fairview at Mecox has beautiful flowers throughout the Summer. Right now they have a corn maze and a corn cannon, which is the coolest thing ever! Basically it’s a long air rifle that shoots dried out corn towards a target. Hit the target, win a prize. I had never seen such a thing and I loved it! You can of course select your own pumpkin from their huge field. You’ll also find lots of treats like popcorn, cider and cider donuts. This farm is super kid-friendly with lots of areas they can run, play and explore in.
Just across the way is Milk Pail, which is part farm and part orchard. They mostly pre-pick their pumpkins and gourds and keep them along the grassy parking lot, but you can buy a half-peck or peck bag and pick your own apples. Milk Pail has so many varieties to choose from! I skipped a few steps and instead got some of their famous apple cider donuts (one bag with cinnamon sugar and one bag without!) and an apple crisp.
I had a chance to wear five different outfits for our fun day pumpkin and apple picking, so I feel like an expert in what to recommend! My first outfit of 5 Perfect Pumpkin or Apple picking outfits features a perfectly Fall color combo — black and brown!
Firstly let me say that I love the boots I have on here but heels are not a good idea for a day at the farm. And as a former FFA member I know better…but my flat suede boots are getting repaired right now, so these were the only ones in my closet for the shoot! Sometimes you gotta do it for the ‘Gram, right? 😉 They are great boots though and athletic calf-friendly! I’m in the wide calf here. Here’s another OOTD with them (it’s the second outfit in that post).
This dress was an impulse pickup after seeing Carolyn’s beautiful styling. It’s such a fun knit! I love brown and black together — chic for the city or the farm! I’ll have more styling ideas for this dress on my Instagram so make sure you’re following along.
Chilly weather is the perfect time for a long cardigan, don’t you agree? I love the huge pom pom sleeves on this cardigan! It’s such a fun fashions statement and keeps my hands extra warm. That’s very helpful for events when you want your hands easily accessible, like pumpkin or apple picking!
I don’t normally think to combine pink and green but the result is excellent here! (I have more examples of successful pink and green stylings on my Street Style Pinterest board — are you following it yet for inspiration?).
I brought out these colors with the rest of my accessories. The bag is pink but could read as brown, especially when paired with brown boots and a brown hat! I also love my green necklace so much because it brings out my green eyes beautifully. Most of all this outfit is super comfy for a day walking around fields of pumpkins or apples. That’s why it’s 1 of my 5 Perfect Pumpkin or Apple picking outfits!!
You can more looks at the boots on me here. (I’m wearing them in the second and third outfits.)
There may be just a hint of a chill this time of year rather than true cold. In that case, a lightweight dress works wonders! This lightweight H&M dress has such pretty details. There are gold beads on the drawstring empire waist and beautiful butterfly sleeves. I’ve paired it with a lightweight jacket in the ever-popular Anthropologie Faravel Moto Jacket. And then for fun, I wore leopard print socks with my mules!
A maxi dress is an excellent choice for the day at the farm! It not only protects my legs from sun, pests or chill, it also makes sure I’m not accidentally flashing people when I bend over to pick up a pumpkin! (We saw so many butt cracks in the fields. I guess people flash their butts inadvertently even in the Hamptons!)
For whatever reason, this was the look that garnered the most compliments during our day at the farms. And guess which part people liked the most? The socks-mules combo!! I was shocked. No fewer than four ladies asked me where I got them. You can see me rocking socks with these mules in this post too. I guess it’s a trend…?
I can’t believe it took this long into the post to talk about flannel!! Not only is flannel a terrific layering piece it is also the epitome of Fall! I’m in love with this cabin print. It’s a couple of years old from American Eagle — I purchased it on Poshmark. Here are this year’s colors.
I paired the flannel with a pair of boots that is going on 3 years strong without needing new soles, toes or heel repair. That is remarkable for this New York City girl who clocks in over 10 miles each workday walking. The heel is low and blocky enough on these that I didn’t have any issues walking in them. Like the pair topping the post I’m in the wide calf version. My calves are about 16.5″ around these days. (Just a little too big for Frye, darn it! But fitting in more Stuart Weitzmans.)
I really don’t know how people dressed for Fall before plaid and flannel. Such miracles should be celebrated by wearing plaid flannel as much as possible I think!
Did you notice that this post only features four of my 5 Perfect Pumpkin or Apple picking outfits? You’ll have to head to my liketoknow.it page for an exclusive look at the 5th outfit! I highly recommend you follow me there for an exclusive look at some of my outfits, including my actual #OOTD selfies.
Also, you may have noticed that this post mixes a bunch of old items with the newer pieces. This is a conscious decision I’ve made this year. No one needs new clothing everyday. I have so many ‘old’ pieces in my closet that I enjoy wearing often. It only makes sense to include those in my outfit posts too! With so many resale sites now it’s not as hard as it once was to find these items secondhand.
I love working with brands and showcasing their newest items! That will continue as well.
Want even more pumpkin or apple picking outfit inspiration? Follow my Street Style Pinterest board — or you’ll miss out on so many great outfit ideas! Which of these 4 outfits is your favorite?