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Boston Apple Picking Fall Family Outfits (mom, toddler son)

While apple picking is a New England must-do every Fall, what our family really looks forward to is Asian pear picking! Crisp, sweet, and juicy – the kids can’t get enough, and they last nicely in the fridge through winter. Our usual spot is Parlee Farm north of Boston, but for Asian pears and the vast kids play areas, we suck up and pay the pricier admission at Lookout Farm.

Wanted to share an outfit I wore recently, and some boys & girls clothing and shoes that I’ve been very happy with (durability, comfort, and style-wise) and would highly recommend!

apple picking family pic 2024 lookout farm bostonapple picking family pic 2024 lookout farm boston

One of my default outfit formulas for these warmer fall weekends has been a relaxed chunky sweater paired with a skort. The skort is cute but practical for bending over and keeping up with the kids, and a sweater adds a cozy touch. I pair with sneakers to dress it down or tall boots for a chic fall look. This Quince sweater (6 colors) is a nice quality knit and weight, and one of the colorways has a mom & me kids version!

I also have to call out this Sezane cotton waffle shirt since Nick loved it so much, he bought both colors last spring. Size up if between sizes. He wears them every week and they’re still in great shape! J.Crew also has a similar looking version for half the price.

A few kidswear winners

After much trial and error and returns, I wanted to share a few cute winners in the kids department that are comfy and durable. Both kids also only want easy pull-on, pull-off bottoms.

Abercrombie kids:
Nori asked for skorts and flare leggings with pockets, and the winners were actually from Abercrombie kids. This active pleated skort with matching sweatshirt is also very cute and has been machine washed countless times without issues, and there’s a new sweater knit version that I added to my own list! Some of you can probably fit the big kids sizing yourself – I tried their kids 13 and it was a little big on me, so might try a size down next.

abercrombie kids girls outfit, woom bikes toddlerabercrombie kids girls outfit, woom bikes toddler

H&M kids:
For Rio (who has a slim build), my challenge is that while so many kids waistbands have a drawstring, once I tie it tight enough for his waist, he’s unable to pull them up and down at school.

These H&M cargo joggers have a more “streetwear” vibe over regular sweatpants plus pockets, and are soo soft and comfy. The best part: an adjustable inner button elastic waistband that I wish EVERY kids bottoms came with. I bought 4 colors and the next size up to grow into! Some of the colors come with a matching hoodie for a full set.

Other H&M kids keepers that we buy repeatedly in bigger sizes:

little girls fall style black boots trench coatlittle girls fall style black boots trench coat

Boots & Sneakers

1. Girls boots.
Last fall Nori also asked for black boots “like mom’s” and these seemed lightweight, comfy off the bat and TTS. They have a side zipper for easy on, easy off, and come in both a regular version and a fleece lined one for winter. Another Amazon find is these bow clips I bought for myself that she loves borrowing for dressing up a simple ponytail!

    2. Supportive, durable sneakers under $50 (also in toddler sizes for less).
    For a supportive sneaker that lasts through hard wear & tear, we swear by these Saucony velcro shoes and have bought them in at least 3 sizes. They’re comfy for all day with no breaking in, and actually lasted until she outgrew them (without getting torn up or the velcro stops sticking, etc).

    MA boston pumpkin patch family outfitsMA boston pumpkin patch family outfits

    3. Stylish Adidas sneakers for the family

    I absolutely love the preppy green suede of these Adidas Gazelles (a Foot Locker exclusive, apparently), and the kids like how lightweight they are for running around. The darker color also holds up well for kids and masks dirt and stains.

    This style runs a little big and comes in big kids sizing, which can easily fit adults. I tried the big kids size 4 and sadly had to return as it was too big for me, fitting like a womens 6. So someone my size might be able to fit a Preschool kids 3, which the size chart equates to a 35. Here’s all the sizes available:

    • Toddler with velcro straps: in toddler 4 to 10
    • Preschool: in toddler 11 to kids 3
    • Grade school: in big kids 4 to 7 (which might equate to a womens 9/10)


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