OOTD: 5 Perfect Pumpkin or Apple picking outfits

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OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy
Found the perfect pumpkin for our apartment!

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.

OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy
Dress: H&M | Jacket: Blank NYC via Nordstrom (also love this one!)
Boots: JustFab | Necklace: J.Crew | Bag: Valentino via Farfetch 
Sunglasses: Ray-Ban via Nordstrom | Earrings: H&M

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.

5 Perfect Pumpkin or Apple Picking Outfits: Outfit #1


OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy

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?).

OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy
Dress: Leith via NordstromNecklace: J.Crew | Sunglasses: Madewell
Boots: Walmart | Bag: H&M

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.)

5 Perfect Pumpkin or Apple Picking Outfits: Outfit #2


OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy

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!

OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy
Jacket: Anthropologie | Dress: H&M | Hat: H&MBag: H&M 
Mules: Madewell | Socks: Madewell | Sunglasses: Gucci via Net-A-Porter

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…?

5 Perfect Pumpkin or Apple Picking Outfits: Outfit #3


OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy

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.)

OOTD: 5 Perfect Pumpkin or Apple picking outfits :: Effortlessly with Roxy
Necklace: J.Crew  | Flannel: American Eagle via Poshmark (here’s an XS!)
Tank: Aerie | Bag: Madewell | Jeans: American Eagle | Boots: JustFab
Sunglasses: Ray-Ban via Nordstrom

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!

5 Perfect Pumpkin or Apple Picking Outfits: Outfit #4

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?


  1. Rach DiMare
    October 8, 2019 / 8:56 am

    I'm so impressed that you got 5 different outfits! I love that H&M dress. So cute!

    • October 8, 2019 / 10:25 pm

      lol thanks Rach! I don't normally do so many outfits in a single shoot, but Vanessa was game and I wasn't sure if I'd make out back out to the Hamptons before apple season was over!

  2. October 8, 2019 / 10:18 am

    Really cute boots and I love the purse you had in the first picture. I never thought of wearing a dress for this activity but it will definitely be a perfect photoshoot session.

    • October 8, 2019 / 10:26 pm

      Yes! I am so accustomed to wearing dresses now that it's hard for to remember that there are other options out there!

  3. October 8, 2019 / 12:07 pm

    These fall outfits are GORGEOUS! Love the first one!

    • October 8, 2019 / 10:26 pm

      Thank you so much!

  4. October 8, 2019 / 12:50 pm

    Oh my gosh, all of these are so cute! I really love the mxi dress outfit but I’d wear any of them! I’ll be drawing some outfit inspo from you when I visit the pumpkin patch (and hopefully if I go apple picking!)!

    • October 8, 2019 / 10:26 pm

      Love it and can't wait to see your looks!!

  5. October 8, 2019 / 2:36 pm

    Girl I love these outfits! I'm going apple picking and pumpkin picking soon, and this was the inspo I desperately needed!

    • October 8, 2019 / 10:27 pm

      So happy to hear this!!

  6. Sima
    October 8, 2019 / 3:19 pm

    Cute outfits but I cannot imagine apple picking in anything that nice. The apple orchards near us are prone to get muddy, with multiple decaying apples on the ground.

    • October 8, 2019 / 10:35 pm

      Fair!! We were out on a sunny, dry day so mud was not a concern.

  7. October 8, 2019 / 7:02 pm

    This has me so excited for Fall! What a beautiful dress too!

    • October 8, 2019 / 10:35 pm

      Thank you Lavenda!

  8. October 8, 2019 / 7:40 pm

    Loving all these fall looks on you! They are perfect for pumpkin picking- love the maxi dress on you xoxo sarah

    • October 8, 2019 / 10:35 pm

      Thank you Sarah!

  9. rachelritlop1
    October 8, 2019 / 8:09 pm

    such a cute look for pumpkin picking! Loveee the patch you're at too!

    • October 8, 2019 / 10:35 pm

      Such a fun area. 🙂 Love our Hamptons weekends!

  10. babygotbalance
    October 8, 2019 / 8:59 pm

    These are all so cute! I love all the boots.

    • October 8, 2019 / 10:36 pm

      Thank you! JustFab is great for peeps with wide calves like me. 🙂

  11. luvlucytoo
    October 8, 2019 / 9:48 pm

    The H&M dress is sold out. 🙁
    LOVE that you are mixing "oldies but goodies" with newer items!!!

    • October 8, 2019 / 10:36 pm

      Bummer, but H&M restocks often! Yes so fun playing with old and new stuff!!

  12. legalleeblondeblog
    October 8, 2019 / 10:40 pm

    cute outfits – my favorite is the plaid top and jeans!

    • October 9, 2019 / 9:26 pm

      Thank you very much!

  13. October 8, 2019 / 10:51 pm

    I went apple picking for the first time last year, and I absolutely loved it. I’m also going pumpkin picking too. Plaid is definite must for me during the fall. I love your last outfit so much!

    • October 9, 2019 / 9:27 pm

      Thank you!

  14. October 8, 2019 / 11:29 pm

    Loving this cute outfits!! The dresses are so cute, especially paired with a chunky cardigan!!

    • October 9, 2019 / 9:27 pm

      Yes the chunky cardi is such a fun piece!! It really keeps me warm when needed too.

  15. Sarah Forest at Ponder Trail
    October 9, 2019 / 1:31 am

    These outfits are all so cute! Perfect for fall! I can't wait to go pumpkin picking this year. It's one of my favorite autumn things to do. 🙂

    • October 9, 2019 / 9:29 pm

      It's so much fun! I like that they have so many different sizes of pumpkins because our apartment could not handle a huge one.

  16. Emily
    October 9, 2019 / 8:01 am

    I love that green and white dress! So so cute!

    • October 9, 2019 / 9:29 pm

      Thank you it is part of the H&M Conscious Collection!!

  17. October 9, 2019 / 8:18 am

    It's still so HOT where I am that I'm going to have to wear shorts and a t-shirt when I go this weekend. UG! I love the look of jeans with the flannel, though. 🙂

    • October 9, 2019 / 9:31 pm

      Oh wow it was hot here until this week!

  18. October 9, 2019 / 8:24 am

    The flannel look is definitely my favorite. I'm awkward so I think it would be much easier to go apple or pumpkin picking in jeans than in a dress!

    • October 9, 2019 / 9:32 pm

      I totally get that. If I had unpacked my leggings from my seasonal storage I might have worn those!

  19. She Saw Style
    October 9, 2019 / 9:32 am

    Oh my gosh, I'm jealous! I still have yet to go to a pumpkin patch, but I'm hoping to make a trip in the next few weeks with my husband, so we can decorate before Halloween! Love these looks – especially the plaid flannel!

    • October 9, 2019 / 9:32 pm

      You guys will have so much fun!!

  20. Christa Anne
    October 9, 2019 / 10:29 am

    You look so pretty! I love all of these outfits but that plaid button down is definitely my favorite. It’s such a perfect fall look.

    • October 9, 2019 / 9:33 pm

      Thank you! I can see the plaid is clearly the favorite.

  21. October 9, 2019 / 10:29 am

    So many different cute looks! But I think that bubble sleeve long cardi is my favorite!

    • October 9, 2019 / 9:33 pm

      It's so much fun to wear!!

  22. aisasami
    October 9, 2019 / 11:40 am

    I love the dresses you featured in this post, especially the green and white ones! I also can't believe they are from H&M! I have to go there and find these dresses!

    • October 9, 2019 / 9:41 pm

      I know! H&M has gotten really cute in the last 2 or 3 months.

  23. October 9, 2019 / 12:44 pm

    Flat boots for the win! I wore mine apple picking a few years ago and I think the trick is to wear a faux leather that's easily wipeable to get all the dirt and dust off.

    • October 9, 2019 / 9:41 pm

      Woohoo! That's a great suggestion. I also love wearing my Nike Flyknits that I can just throw in the washing machine!

  24. Kate
    October 9, 2019 / 1:02 pm

    Yes, please do continue to post old mixed with new! Isn't that how most of us dress? We mix the new stuff we buy with the things already in our closet, perhaps freshening them up and giving them a new look.

    • October 9, 2019 / 9:41 pm

      Yes! The blogging world is certainly different but I'm enjoying mixing things up. 🙂

  25. October 9, 2019 / 8:07 pm

    I love pumpkin picking season! my go-to is a soft flannel, so I love your last option!

    • October 9, 2019 / 9:42 pm

      You can't go wrong with flannel!

  26. October 10, 2019 / 5:25 pm

    I am so excited for pumpkin picking season! I loft a good flannel top and some knee high boots. I hope the rain holds out!

  27. October 10, 2019 / 7:26 pm

    Lovely OOTD! I love picking pumpkin but haven't tried it. Will definitely try this some time.

  28. Molly Moon
    October 10, 2019 / 11:36 pm

    Loving all of these fall outfits! I'm trying to convince my husband to go apple picking this weekend. Looks like you had a blast!

  29. Kristina
    October 11, 2019 / 8:03 am

    That printed maxi and olive jacket are my fave and love that giant pumpkin!!

  30. October 14, 2019 / 3:41 pm

    So many cute looks– these pics make me want to head to the pumpkin patch ASAP!

  31. October 15, 2019 / 10:52 am

    I love the plaid outfit! I am so excited to fo pumpkin picking this season 🙂

  32. CIMINO61
    October 23, 2021 / 12:38 am

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