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Fall· Fashion

Back To School Pop-Up Sale

This post is sponsored by Macy’s & ShopStyle.
All opinions are 100% honest & all items were hand-selected by us.

fall family style

The school year is just around the corner (if your kids haven’t already started) – mine have a few more weeks of summer vacation, so we’ve been trying to make the most of the time we have left before the busyness of their new schedules begin.  This is a red-letter year for us because we will have one in high school & one in middle school.  While having both a pre-teen & a teenager certainly comes with its challenges (& gray hairs!), it’s also such a fun phase because they are getting more independent and really coming into their own.

School clothes shopping can be a struggle, regardless of your kids’ ages, and I feel like I’ve finally figured out the best way to tackle the process without getting pushback from my kids.  Rather than dragging them all around the mall & forcing them to spend hours in a fitting room, I create a stress-free shopping environment at home.  I bake some cookies, put on their favorite music and we sit down together at my computer to browse through the new arrivals for fall.  Today we’re sharing what we picked up from Macy’s + highlighting their Back-To-School Pop-Up Sale that’s going on today & tomorrow!

family fall photos

Those of you who are moms know that you have to pick your battles and I decided long ago to let my kids choose what they wanted to wear.  I think it’s important to let them have that individuality, to allow them to try different things so they can learn what they like & develop their own personal style, even if it’s different than what I would choose for them.

For example, my daughter was such a girly girl when she was little and wanted to wear outfits with ruffles and any dress that was “twirly”.  But, when she hit her preteen years, she went through a tomboy phase where she only cared about being comfortable.  Now that she’s almost 16, she’s found a good balance between the two and her style has really matured…to the point where we can borrow from each other’s closets now, which I love!

kids back to school sale

juniors back to school outfit

I can hardly believe that she will be a sophomore – only two more years at home before she leaves for college (cue the waterworks!).  Since she has pretty much stopped growing, I feel better about spending a little more on clothes knowing they will last her for a while.  We’ve started working on creating a mix & match wardrobe of versatile classic pieces with just a few trendy items thrown in.  She loved this cardigan so much that we bought it in multiple colors (she also picked up the dark gray & burgundy).  It’s the perfect weight & length (she’s 5’8″), it has pockets + you can’t beat the price.  I’ll definitely be stealing this from her!

She layered it over this floral print cami (which she also plans to wear under this jacket).  The cami runs a little big, so I’d recommend sizing down – it also comes in a dark floral & a snakeskin print (I couldn’t resist buying for myself!).  And she was thrilled to discover this brand of jeans because they fit her perfectly – denim is always a struggle because her waist is much smaller than the rest of her bottom half, so usually she has gaping at the back of the waist.  But, these fit like a glove, so we ordered more in olive green, burgundy & black.  For reference, she normally wears a women’s size 8 in denim, and she ended up getting the juniors’ size 9 in these.

mother daughter style

Maison Jules Cardigan

Her outfit details:
c/o Maison Jules Cardigan, c/o Hippie Rose Juniors’ Camisole,
c/o Celebrity Pink Juniors’ Jeans, c/o Dr. Scholl’s Flats

Like many boys, my son went through a phase where he would only wear athletic clothing, so now that he has outgrown it & actually wants to dress a bit nicer, I’m taking full advantage!  He is at a tricky spot right now because he’s so tall/big for his age, which puts him right between the kid’s & men’s sizing.  The key for us has been finding brands that go all the way up to a boys’ size 20 and men’s brands that offer an XS.  So, if you have a son who is stuck in the same place or if you need some fall clothes for your teen or husband, these will be great options to check out while they’re on sale!

Macy's Back To School Outfits

boys first day of school outfit

He is really picky about how clothes feel, and I’ve learned the hard way that if they’re not soft or stretchy, they will sit in his closet & never get worn.  So, rest assured that every recommendation we’re making here passed his comfort test with flying colors!  This super-soft henley is so lightweight, which makes it ideal for early fall temperatures, and it comes in 4 different colors – I was actually thrilled that this was a little long on him because that means it will still fit as he gets taller.

Because he’s so active, he hates denim that is stiff, so the stretch in these jeans was perfect for him!  I’ve been wanting to get him a pair of non-athletic sneakers that he can wear to church & with nicer casual outfits and he loved the color of these.  I went up half a size so they’ll still fit when his foot grows, but I’d say these run true to size.  My husband keeps eyeing them, so that I might grab him a pair too!  Other items we loved & kept: these black sneakers, these joggers (with reinforced knees!), this zip-front hoodie and this burgundy tee (he plans to layer under this bomber jacket).  See more of our top fall picks for the whole family below!

American Rag Henley

mother son fall style

His outfit details:
c/o American Rag Men’s Henley, c/o Calvin Klein Boys’ Jeans,
c/o Tommy Hilfiger Men’s Sneakers

My outfit details:
c/o Sanctuary Sweater, c/o Jockey Camisole, c/o Lucky Brand Jeans,
c/o Chinese Laundry Boots, c/o Essentials Hoop Earrings

WOMEN’S & JUNIOR’S FALL PICKS

BOY’S & MEN’S FALL PICKS

08.12.19 Kimberly

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Penny Pincher Fashion is a part of several affiliate networks. This means when you click on links to various merchants on this site and/or make a purchase, this may result in a commission that is credited to PPF. Also, as an Amazon Associate I earn from qualifying purchases. I take the responsibility of recommending products very seriously & will link to items that I personally love.

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