Casual Fall: Apple picking and cider donuts around Boston

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DIY top (similar), J.Brand legging jeans in 24, hemmed (similar), Kenna-T Jacket c/o, Sperry Audrey shoes c/o (on sale w/ extra 25% using FRIENDS) (all sizes left here), Target chambray shirt

We just waved goodbye to the last batch of visiting friends this month (all of whom happened to be from CA). Two of them had never set foot on the east coast before, so we made sure to share some of our favorite things to do in New England. There were plenty of fresh lobster and oysters, hot chocolate, long walks around the city, foliage peeping and of course apple picking. This summer was my first time at a berry farm, but visiting apple orchards is a tradition I look forward to every fall.

apple picking2

For a comfy outfit that allows for easily climbing, I started with a formula of casual staples – my favorite dark skinny jeans, chambray shirt, plus as warm leather jacket. This pairing was fine as-is, but I experimented with a striped top (last styled for summer here and here) as an additional layer and rather liked the results. There’s something fun about the hint of chambray as a collar, and the flared peplum hem peeping out from beneath the jacket. A pair of slip-on flats continued the theme of navy and neutrals.

apple picking

I picked these out at the Natick Mall Sperry opening several months ago, and they are now some of the most functional (especially for rainy day commutes, given the non-slip sole) shoes I own. I tried on most of the classics, but personally loved this more girly “Audrey” style with a lower vamp. My favorite color/material combo (tons of choices) is the cognac leather with navy patent. Patent leather seems to be a little more water resistant, plus is very easy to wipe clean.

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I found the size 5s to run a little big, comparable to a 5.5 in most brands. The leather laces go around the back, and can be tied tighter up front for a more snug fit throughout. To prevent the back sides from rubbing my lower ankles, I added heel cushions (as shown here) which worked like a charm. I personally thought this style was a bit more narrow in the toe area, and it did take a day of breaking in before they became very comfortable.

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Some orchards offer fresh cider donuts and pressed cider (happy sigh), amongst other treats. This place had a warm apple dumpling a la mode special that day – turned out to be an excellent choice.

apple picking4

The apple picking season around here only goes through late October, but Tougas Farms in Northboro, MA (less than an hour drive from Boston) still had plenty of apples and pumpkins as of last weekend. Admission was $20 for up to 4 people, plus an empty bag that holds at least 10 lbs of apples (a nearby orchard allows 2 adults + 1 child for $16). They are more than ok with munching around as you pick – only rule is if you take a bite, you must not waste the apple!


57 thoughts on “Casual Fall: Apple picking and cider donuts around Boston

  • F. K. October 23, 2013 at 11:21 pm

    That jacket and top is so nice! I bet the apples are delicious. 🙂

  • saystheprincess October 23, 2013 at 11:46 pm

    I've been looking for a farm that still has apple picking! yay!

  • Tayler Worrell October 23, 2013 at 11:52 pm

    I just went apple picking for my first time this september while I was visiting loved ones in New England. It bame my new favorite!! I wish we had more apple farms here in the PNW.

    You look great!


  • Paula October 24, 2013 at 12:03 am

    I love apple picking! My produce drawers are so heavy from the weight of so much apples. Have you tried Honey Pot Orchards? Though it's seems to be a favorite amongst Bostonians, I go to George Hill instead.

    I really like how you layered the chambray shirt with your striped top 🙂

  • I am Khatu October 24, 2013 at 12:07 am

    Stop it, this is too cute! Kudos to the photog.

  • Le monde des petites October 24, 2013 at 1:54 am

    What beautiful pictures!!!!
    Love your jacket so much!!!!

    Le monde des petites

  • Dressed with soul October 24, 2013 at 2:06 am

    Yes, the apples caught immediately also my attention because here in Bavaria the apples on our tree were destroyed by a hail storm in early Summer and of this cause our apple harvest was zero …

    Great casual outfit <3

    xx from Bavaria/Germany, Rena

  • k come karolina October 24, 2013 at 3:45 am

    you look amazing!

    xoxo from rome

  • Carol Li October 24, 2013 at 3:50 am

    I love your outfit and your first photo looks so professional 🙂

  • Mady T. October 24, 2013 at 4:03 am

    love the jacket! cute outfit!


  • Rachelle ( October 24, 2013 at 5:31 am

    You look adorable love those sperry you are wearing.


  • youngandfoolish October 24, 2013 at 5:46 am

    Sperrys are absolutely my favorite commuting shoe. For some reason the women's cushioning seems to fare much better than men's, making it as comfy as a tennis shoe! I live in San Francisco and usually walk about a mile to / from work, up and down hills, and I love them. They're not as stylish as flats or heels, but definitely durable and much preferable to flip flops!

  • Anissa Uusikangas October 24, 2013 at 6:49 am

    Gorgeous pics <3

  • Lam Lam October 24, 2013 at 8:37 am

    Absolutely beautiful! Love the casual look but still so put together <3

  • dee October 24, 2013 at 9:33 am

    I love your whole look! Oh and apple picking. I haven't gone this season yet and I'm so sad that it's almost over! 🙁

  • Elle FFNFF October 24, 2013 at 9:40 am

    My mouth is watering…I too recently went apple-picking and the taste of cinnamon cider donuts is still fresh on my tongue.

    And these photos are so lovely! I hope I get to tag along on your shoots when I am there! 🙂

  • Laura October 24, 2013 at 9:47 am

    Really love that jacket – the quilting on the shoulders and the color are fantastic!

  • FashionEdible October 24, 2013 at 12:13 pm

    Beautiful outfit Jean. That jacket has got to be one of the best designed jackets I've seen. I love the hint of chambray you added underneath your DIY top.

  • Bárbara Eirís October 24, 2013 at 12:37 pm

    Funny and beautiful pictures!!

  • Mei Fleming October 24, 2013 at 2:21 pm

    Cute outfit AND photos!

    NEW POST:: PRINT-mania
    Take a look!…

    thanks!! xoxo

  • Jessy October 24, 2013 at 2:43 pm

    I love the last few pics! The outfit is so cute! I would've never thought to layer a chambray under a peplum top. The pieces are so opposite, but it works in this look! I've never gone apple picking before (or maybe I did when I was a kid)… it looks like a lot of fun!

  • Plum Pretty Sugar October 24, 2013 at 6:23 pm

    What a beautiful setting!


  • Alma Affaires October 24, 2013 at 8:29 pm

    This comment has been removed by the author.

  • Alma October 24, 2013 at 8:31 pm

    Cute photos! I love apple picking and making apple wine in the fall!

  • Meghan October 24, 2013 at 9:41 pm

    What size Sperrys did you buy? I have been hunting for a pair of Sperrys for forever, but I have size 5 feet. The adult size 5 is far too big, and the kids sizes fit but the designs look childish. Any advice? Just wondering if Sperrys tend to run large?

  • Meghana October 24, 2013 at 9:42 pm

    Oh never mind, you discussed this! I should have read closer. Ps. Love your blog!!

  • Suzie Q October 24, 2013 at 10:14 pm

    This post reminds me that I still need to experience apple picking since moving to the east coast! The desserts all look so yummy! I've never been a fan of boat shoes, but the way you styled yours look make them look so cute!

    Suzie Q

  • Jean October 25, 2013 at 4:28 pm

    Hope you like it there! Honey Pot Orchards was also still open this week but it's a bit more popular so could be more crowded.

  • Jean October 25, 2013 at 4:28 pm

    We were headed to Honey Pot until I read that the admission only covers up to 3 adults and any extra would be another $16! I'll have to check out George Hill next year : )

  • Anonymous October 25, 2013 at 6:07 pm

    Holy cow! I'm from Northboro! Found your site a little while back, love it,and have been lurking ever since, but just had to comment today. Thanks for all the great advice. I have more curves than you do so can't quite wear the same looks at times, but the sale advice is so valuable and your pictures are always gorgeous!

  • I am A Love Addict October 25, 2013 at 6:36 pm
  • Anonymous October 25, 2013 at 11:27 pm

    Hey Jean! I just want to say that I saw you at my local loft today….I mean your poster… hehe. The poster of you was huge. I went inside loft of shop, but then I saw a big poster on the wall, and I have to do a double take to see if it's really you on it. It is! You look great in the poster.

    I adore your blog and your sense of fashion.


  • Anonymous October 25, 2013 at 11:56 pm

    I'm going to try chambray underneath a striped top tomorrow! I really Love the way it looks.Thanks for sharing your outfit ideas. I'm a busy mom and I don't always have time to experiment.

  • rodelma lopez October 26, 2013 at 3:30 am

    Like the outfit the leather jacket esp…delicious apples I love gala apples the most

  • Michelle October 26, 2013 at 5:32 am

    Ha, glad to have another person on the Sperry bandwagon! It's a comfy place over here 🙂 I reco'ed them a long time ago on your travel shoes post, glad to see you've got yourself a pair! My sisters and I all wore Sperrys for our 2 week walking vacation around the UK. Comfy and they take a bunch of abuse and wash well!

    Hey, curious, did you ever end up professionally shortening the sleeves on that awesome jacket, or are they still just folded up? I'm trying to hold out for real leather vs polyurethane 🙂

  • B Trendy October 27, 2013 at 11:02 am

    Love the pictures!!! and also the outfit!!! I love the shoes and the jacket!!! these jeans really fits you perfectly!!! have a nice day!

  • Anonymous October 27, 2013 at 12:28 pm

    Hi Jean, your blog is a great resource for petites (I'm 5"1'). I learned a lot from the posts about how the right fitting makes a big difference. I love your color combinations too!

  • Anonymous October 27, 2013 at 2:16 pm

    The J Brand legging jeans look great! I've been searching for a month now for perfect premium jeans in the $100-200 range (that i wouldn't have to hem…dare to dream) and thought I would share for those also looking…After ordering and returning from Amazon, nordstroms, zappos… I just located perfect premium Jeans (no hemming needed!) at my local Anthropologie yesterday in CT. They now have a petite's section and carry several premium brands (J Brand, AG, Pilcro, etc.). I'm 5'2" and 110# and the AG Legging Jeans (so soft) in size 26P/27P fit perfectly length wise (no hemming needed!!). I'm normally a size 0P or 2P at Gap/Banana. The AG straight leg and J Brand in petite fit lengthwise too. Pilcro was also great were too short for me (I never thought that day would come). They had lots of size 24P and 25P for those who are 00P. Unfortunately I paid full price. Thought i would share.

    this is their online selection (by the way, if you use paypal they won't let you return at the store except for merchandise credit)

  • ChooAddikt October 27, 2013 at 4:01 pm

    Your blog has inspired me to get a pair of Sperry's! So thanks for sharing 🙂

  • Mihirani Sourjah October 28, 2013 at 3:37 am
  • ordinette October 28, 2013 at 4:08 am

    Your blog is Amazing and your creations just fabulous. I am following you on bloglovin.
    laura from Rome

  • kileen valenzuela October 28, 2013 at 11:23 am

    looks like you had a great time apple picking! i love the striped peplum layered underneath the jacket and it's such a chic casual look!

  • Meevin October 28, 2013 at 1:53 pm

    Do you model for Ann Taylor Loft Petite? There's a giant poster of you in the store window at my local Loft.

  • Petitetomatoes October 28, 2013 at 2:21 pm

    Those apples look so refreshing!

  • Hook Namburi October 28, 2013 at 3:56 pm

    uumm, i am a guy and i just recently discovered this blog. i believe i am addicted. the posts are great and the pictures are even better. i can't believe i just only now found this website!

  • The Internet and The Unicorn October 28, 2013 at 8:45 pm

    You look fabulous Jean! I liked how you used the red jacket to compliment the red apples and the green leaves. The different shades of red really plays off each other well. I'm actually heading out to Wellfleet in a few months (yes the dead of winter!).

  • Jean October 28, 2013 at 11:14 pm

    Hi Meevin! I worked with them for their fall petites campaign. I'm excited that you came across one of the photos! : )

  • Jean October 28, 2013 at 11:20 pm

    Great to hear you found success in your denim search! Thanks for sharing about your experiences. I wish Anthropologie would start opening up more petite boutiques at their stores (so far I hear it's just in 1 or 2 locations) as their selection seems really great.

  • Jean October 28, 2013 at 11:20 pm

    Thanks so much for stopping by!

  • Jean October 28, 2013 at 11:22 pm

    Haha I have every intention of getting them professionally shortened (brought it in to tailor for quote and everything) but he asked for 2 weeks, and I'm getting too much wear out of it before brutal winter hits to let go of it now so am making do with folded under.

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