Disclosure: I am a member of the Sears Blogger Squad and was compensated for this post. All opinions, as always, are my own. Thank you for your continued support of STSL! <3
I don’t know if it’s just me or not, but I swear, the back to school shopping seems to be starting earlier and earlier every year. I mean, I’m not crazy, right? Doesn’t it seem like all shopping events in general (i.e., Christmas, etc.) seem to be starting sooner?
Then again, aren’t some of the kiddos heading back in just a few short weeks? I remember the first time (many years ago, of course) I found out that some schools go back in August. At first I was like, “whaaat!? They get a super short summer!” but then not everyone has the same schedule as us here in upstate NY. DUH.
I can still remember back to school shopping from when I was younger just like it was yesterday, and every year it was the same. Towards the mid-end of August, my grandma would go with me, my brother, and my mom, and she would be sweet enough to buy us some brand new outfits for the coming school year. We’d hit up the mall, make a day of it, and my brother and I would each whine and complain about when we had to shop in the others’ department. ;)
Throwback to first day of 3rd grade with my bestie, Heather!
Within the same week or so, my 2 Nana’s would take me and my brother out shopping for all of our new school supplies. I’d get stocked up on my composition books, Lisa Frank folders and pens, mini sticky notes to “pass notes” in class, and all the other “stuff” you need to start a school year. Of course, because we were with 2 Nana’s, we always got more than what we really needed.
Throwback to first day of 4th grade for me and kindergarten for my brother…clearly, he was more excited about his first day than I was.
Yes, we were spoiled. And my parents totally made out in the back to school process, for sure.
But enough about me heading down memory lane, because I’ve got some great deals to share with you guys today, courtesy of Sears. As part of my partnership with them and being a member of their Blogger Squad, I get the opportunity to not only let you in on some great deals they’re having, but also give you the chance to enter a nice little giveaway. Stick with me, we’ll get there in a minute!
Although my little Lucas technically isn’t in to the “back to school” shopping stage just yet, I have no doubt that back to school shopping can be stressful as a parent. But whether you’re shopping online or driving from store to store, Sears wants to help take the stress off with their integrated retail services like Free Store Pick-up, Reserve It, and In-Vehicle Pick-Up. Plus, they’ve got tons of school apparel, shoes and more for great prices…check it out at Sears.com/backtoschool.
*You can see my full review and experience with Reserve It HERE and In-Vehicle Pick-Up HERE*
I recently gave both of those services another try, and was extremely pleased with both. I’ve said this once and I’ll say it again…I have been hugely impressed with Sears as I’ve continued to work with them this past year. They are really knocking it out of the park!
The first service was Reserve It. I had been looking at some shoes online and found two that really caught my eye, so I decided to utilize the service (since I usually prefer to try shoes on first, if I can!) and reserved this pair of gladiators and this pair of wedge sandals.
The process was super easy and took probably less than two minutes to complete. Just choose your size/color…
Choose your store for pick up…
And make the reservation under your name. That’s it!
When I arrived to the store, I quickly found the Reserve It kiosk in the women’s department, just as my text message reminder told me.
Hey look at that…hello, shoes!
I gave both of them a try and didn’t wind up loving the gladiators, but I did like the wedges so I grabbed those. Cute, right?
The other service I used with the In-Vehicle Pick-Up, to grab a few things for Lucas to head back to…daycare. 
I’ve used this service probably half of a dozen times now, and every single time, they have delivered in the guaranteed 5 minutes or less.
In and out in less than five minutes, without ever having to leave the car. I’m totally ok with that.
I got him these new jeans, another new pair of jeans (because all of his were suddenly too small!) and this cute top. They really have some adorable kids clothes!
So I’m sure many of you out there are going to be getting your back to school shopping on (whether it’s for your kids or yourself!), so definitely be sure to give Sears a look this season. Just a few of their unique styles and brands…
- Bongo offers cutting-edge trends in apparel, accessories and footwear. Whether you’re hitting the halls or a party, celebrate your individuality by mixing the styles in your own way.
- Canyon River Blues is a denim-based collection for girls and boys with relaxed sensibilities. It includes great basics that every girl and boy should have in their closet. Influenced by Americana and bohemia, the brand offers trend-right wovens, innovative knits and graphic tees, all at a great value and price. Mix and match to create a wardrobe of signature looks.
- CRB Girl is made up of twirly skirts, electric colors and embellished denim that have a whimsical feel.
- Amplify lends an urban edge to the traditional jeans-and-a-tee combo. Its styles for boys and young men embody the spirit of the skate/music lifestyle, including quality graphic tees, fleece hoodies, flannels and slim fit jeans.
- Roebuck & Co. is behind an essential collection of affordable heritage pieces that have a fresh aesthetic. Roebuck and Co. offers timeless polos, flannels, fleece and thermals in both eclectic patterns and classic styles.
- Toughskins for girls is big on feminine details, including pastels, florals, metallics and shearling; for boys, it’s all about rough-and-tumble jackets and joggers, plus fresh takes on the latest denim.
- Everlast, falls under the athleisure/comfort fashion trend, which is growing quickly. The Everlast brand has fun fabrics, attention to details and performance capabilities.
- Dockers uniforms for kids and backpacks for every age group are also available.
Get the look at Sears for back to school apparel, shoes and more! Learn more at Sears.com/backtoschool.
So to help get you started on that back to school shopping, Sears wants to give a lucky STSL reader a $50 gift card to spend on anything you want!
To Enter: Leave a comment on this post sharing a favorite back to school shopping story or an item that you’re in need of this back to school season.
I’ll choose a random winner on Friday, July 24th. Good Luck! 
I’m dying for a new school bag and some shoes!
I remember going to Buster Browns with my parents when I was a kid. I loved it!
I loved getting my school supply list and picking out all of the new Lisa Frank folders!
That reserve it looks great esp for an always running mama! Need clothes for my growing boy for “back to school”
I remember Jansport bookbags were the hit when I was in middle school! I loved back to school shopping while I was in school.
I used to love school supply shopping because my mom would always buy us a candy bar to have after our first day! Hershey’s Cookies n Creme was always my choice.
I love love love school supply shopping – I used to stock up on crayola markers – thick and thin because in high school I liked to take notes in color ha ha ha!
I desperately need a new backpack! I spilled coffee in the one I have now and it’s all stained..ew
I used to LOVE going back to school shopping for sneakers, binders, backpacks, pencils/pens, etc, now i find it amusing because I nanny how excited the kids get about the shopping (the the actual back to school part)
My brother and I would always put on a “fashion show” to show off all of our new outfits. I love back to school shopping (even if I am 31)!
I used to scour the ads with my Grandma on what to buy when I was visiting her. Then would shop with her all day. I just went through both of my son’s closets looking for what didn’t fit and getting rid of those to make way for their new clothes. For the first time both boys will be going to public school as my younger one did private Kindergarten last year. It is a whole new transition in our house. One that my pocketbook is looking forward to.
I used to love going shopping with all my cousins! My mom and her sister are super close and every year they thought it would be fun for my brothers and cousins to all go back to school shopping together. While it was definitely crazy at times, it is still one of my favorite traditions/memories growing up!
My favorite back to school memory is spending quality time, just my Mom and I, shopping for school supplies! The puppy folders were my biggest purchase!
I am buying some new fall clothes! I am so ready for the cool fall weather!
I loved back to school shopping. My mom would always take me, and I enjoyed spending that time with just her.
Loved going back to school shopping with my Grandma every summer. She would give us a limit of $100 and we’d go to JCPenney to stock up on all the leggings and hugely oversized t-shirts that were all the rage when I was in elementary school. Good times!
I loved back-to-school shopping but I’m sure my mom didn’t :) I remember going to the outlet stores and stocking up on sweatpants, socks and underwear before going shopping for the ‘real clothes’ and picking out the perfect first-day-of-school outfit. And picking out pens and folders was so fun too!
As a teacher, back-to-school time comes along WAY too fast! Just as important for the teacher to get some new school year outfits, right?
Love those shoes you found!
I once showed up at the bus stop in the same exact outfit as my best friend. I don’t know how we hadn’t discussed our outfits for the “big day” but we obviously did every year after that!
I’d love to grab some new comfy shoes for back to school—I am a teacher and am on my feet all day long :)
Clothes and sneakers! I can’t keep my kids in either, they’re growing SO fast… will definitely need to hit up Sears before school starts!
would love a chic but sturdy backpack
I always had to have the perfect trapper keeper!
I remember shopping for a new outfit when I was going into high school and I was so excited to wear it. My friends even called me up to talk about our first-day-of-school outfits (so as not to show up over- or under-dressed).
Ahh such good memories! I remember being so obsessive about having all my school supplies match, and I would color coordinate my notebooks and binders with each subject haha!
We are in need of everything this new school year haven’t done any shopping yet.
i remember making out like a bandit at places like TJ Maxx and Marshalls for back to school clothes!!
I loved back to school shopping (and had many Lisa Frank products too!) and especially loved when my mom and I would take a day road trip a few hours up north to the outlets in Maine or New Hampshire to do marathon shopping to get ready for the new school year.
Im in need of school uniform pants and just got an awesome shop your way rewards email about clothing being up to 50 percent off for back to school and the gift card if Im the winner will be great for some of the school expenses we have out of pocket
I think I need some jeans :P I have one pair…I think! Hahaha! #fitnessclothesalways
I feel like you wrote my childhood! My grandma would take us back to school shopping and I always felt so cool getting my new Lisa Frank folders!! We always hold off now for the kids to get winter clothes since they usually only wear summer clothes for September :)
I always loved going back to school shopping! I loved getting some new clothes and heading to Staples for back to school supplies
I’m a teacher, and I love starting each school year with a brand new lunch box.
Love those cute wedges you ended up getting!
I’m certainly not going back to school (thank god), but I could always use a cute new comfy dress!
I don’t have one story in particular but I remember being obsessed with getting new pencils, pens, folders, and organizers! I wanted everything to match.
I’m a public school teacher…. so I literally need EVERYTHING. It makes my heart sad when I see back-to-school sales in mid-July! :(
My son could use some new tennis shoes for school.
I just graduated grad school and started my first “big girl” job, so I’m in need of some professional clothes!!
I’m due with baby girl in October and pretty much only have summer maternity clothes, so I’d love to grab a new sweater or two!
I would get some new shoes!
I LOVED going back to school shopping! Though I’ve already graduated from college, I’m still back to school shopping this year, because I’m a first time teacher! The $50 would be GREAT to get some “teacher clothes”!
What don’t we need?! My 5 year old starts kindergarten this year. She keeps growing and when I told her to stop she told me that she has to grow because it’s the law. :)
My daughter is starting middle school this year and is SO excited!! I would let her pick out some clothes to go with her “new middle school look”! ☺️
I would love a pair of nice khakis… oh, and new camis!
I’m in need of some new dresses!
I remember wearing nothing but over-alls in 6th grade! I loved those things, but you won’t catch me in a pair today! Lol
I loved back to school shopping and looked forward to it every year! I would always get warmer clothes and want to wear a new outfit on the first day of school, which would inevitably be the hottest day of the summer!! Hahaha. Oh well. Also, my aunt and uncle would take my sister and I out for dinner on the first day of school and give us gift bags filled with TONS of awesome school supplies! It was the best.
We need new backpacks!
We are in need of back to school EVERYTHING! Jacks has outgrown basically all but one pair of pants and of course his feet never stop growing. Similar to his taste in characters. Last years Ninja turtle backpack is not a Minion backpack. Geez!
I need to buy clothes for my first grader!
We just started back to school clothes shopping yesterday! My daughter picked out a cute skirt for her first day back!
My favorite memory of back to school shopping when I was in elementary school was going to the store, finding my supply list and them picking out all the new supplies! I loveed getting new markers, pencils, and fun binders/folders with animals or Lisa Frank charaters!
I’m expecting my 2nd girl in 5 weeks (ahhh) so I think some nice and comfy mom leggings would be a perfect item to get for “back to school” :) I rarely buy clothes for because I’d rather buy for our girls but I think it would be a good time to purchase something for me!
As a teacher, I still look forward to back-to-school shopping and buying new outfits for the beginning of school!
I always LOVED back to school shopping! My daughter is going into 1st grade this year and I can’t wait to start the shopping!!
I am a school counselor and I love the back to school season ! I always buy a few new outfits (usually from LandsEnd!)
Our Lisa Frank backpacks!! Yes!! 3rd grade was the best because we were finally in the same class haha. Lots of note passing that year! <3
I’d love to pick up some new jeans!
An item I’m need of is definitely a new pair of jeans! It’s been awhile since I had a pair that really felt comfortable and stylish at the same time!
For myself, some work shoes
I was someone’s bus buddy but didn’t get us off on the correct bus stop!
Shoes, shoes and more shoes…… kids feet sure do grow fast!
Well not really a story but have to mention the Trapper Keeper!! It was THE item to get for many years.
I had to wear a uniform up until high school, so back to school shopping consisted if shoes for me… sad!
I still love a fun school supply though! There’s something wonderful about the smell of freshly sharpened pencils.
I’ve always loved going school shopping and my mom always made the day so much fun! I’m looking forward to doing the same for my own daughters someday!
My son starts pre-school in September, so I can’t wait to get him some new clothes!
I actually remembering getting my back to school outfit from Sears in 6th grade! It was a plaid tweety bird outfit, and I thought it was amazing! I would love to make a new memory for my kids, maybe a better/trendier option!
I always remember going to the sketchy uniform warehouse every summer to stock up on school uniforms- I hated the plaid jumpers/skirts and especially the pleated shorts/pants!!
Shoes..I am looking for all the deals on shoes and findinsome good ones
Like you, my siblings and I always were subjected to a first day of school photo. I never minded the first day of school because it was exciting and NEW school supplies and clothes. However, by the fourth day it was usually a bit rougher as all of the new clothes had already been worn, and homework was starting to be assigned. But overall, I enjoyed school and the chance to see friends.
I have always loved back to school shopping. For me it was like the child’s version of our adult “new years” if that makes any sense : )
Love this! We need shoes! My little guy definitely needs a pair of new back to school shoes!
Shoes ☺
I need to get both of my boys lightweight hoodies for the fall!
I’m always looking for new boots once the Fall season starts coming around!
My family would go back to school shopping at the “nice mall” that had stores like Pacific Sunwear, Delia’s, The Limited Too, and 5-7-9.
I used to dread going back to school shopping throughout elementary and middle school! I went to a private Catholic school where we had uniforms and a very strict back to school list that didn’t allow us to get the fun, colorful items all of the public school kids had. I loved the freedom of getting to high school and picking out my own things!
I am hoping to get a teaching job so I would love some back to school clothes for myself or classroom supplies!
We need shoes! My son has destroyed his shoes playing this summer.
I am wanting booties this fall (back to school is, sadly, over for me). I have been looking for black ones for 2 years with no luck. I’m being picky, but I am trying to buy “forever” shoes.
I have always been the kid that loved to go shopping for supplies. I would always get more than I needed, you can never have enough folders for your traper keeper. My oldest is starting kindergarten this year, so I am excited to get him started with his own collection of supplies. Plus some “cool” shoes as he says.
My kids are going into 4th, 1st and pre-k, so we need tons of supplies. I loved back to school shopping as a kid and I still love it!
Omg I used to get so excited when we would go “back to school” shopping. I loved picking out binders and loved me a new Jansport backpack!
I would love some new backpacks for my kids. They would be so excited to go to Sears and pick them out!!
Loved back to school shopping! Living in Buffalo, NY we would usually buy lots of new sweaters & jeans & then the first day of school was always so hot! And we’d either go to school in our new clothes & sweat like mad or wear old stuff.
I was a private school kid so I remember going there to try on white blouses and navy shorts….. of course with new shoes!
My little ones need shoes
For preschool in the fall!
We are definitely in need of a new winter jacket!!
I loved Lisa Frank everything! I also loved going shopping for new clothes before school started. However, once I got to highschool,my mom made me wait until after soccer season for the bulk of it because freshman year I lost 20lbs during the season and she had to buy me all new clothes a few months later because nothing fit!
We would always shop for back to school things on Tax Free weekend here in NC! They did away with that a couple of years ago though!
Jeans
I looooved back to school shopping! We would always come home and model all our new clothes for our dad (I’m sure he was just thrilled :P )
I may not be heading back to school and my daughter is only 10 months but I really need some new tops for work. Myself and I’m sure my coworkers are getting tired of the current rotation :)
gym shoes!
I am in need of some new clothes for sure! I was pregnant last school year, so many of my clothes have been sitting for a long time. I’d love something new!
My little guy starts three day a week preschool in September! Would love this to get him some new outfits!
My birthday is in the beginning of August, so I always remember using my birthday money to buy some new clothes. My parents always let me go pick out new sneakers and I would always think my first day outfit was SUPER COOL. I always school shopped at Wal-Mart, but my first year of high school, I’ll never forget my dad let me school shop at the mall. Thought it was awesome! haha
The most memorable shopping trip was in 5th grade! Just before summer ended, we drove up to Oregon to visit family. While we were there, my parents took advantage of the whole no sales tax and I got the prettiest pair of Reebok Pumps [totally dating myself here]…with the actual basketball shaped pump on the tongue. I was such a tomboy and felt awesome rockin’ those kicks on the 1st day of school!!!
I wonder if my kids get this excited about their back to school digs!?
I’m in need of new clothes for my 16 month old daughter.
i used to love back to school shopping with my mom because she would let me get come stylish new clothes for the year
Both my kids need jeans desperately!!
My daughter could use some back to school jeans!
Back to school shopping with friends was a blast!
I love back to school shopping! My little boy will be starting kindergarten this year and will need some new jeans!
Some dorm decor!
I really need a light jacket for the fall weather…all the ones I like sell out so fast! :-(
My kiddos really need pants and tops this school year. They’re growing like weeds :)
I have never seen a delivery service such as that, how awesome! For back to school, I would definitely love to have some make up! I have always been afraid to try wearing any, but I’d love to be able to enjoy putting some on when I go back to school this year :).
Lisa Frank supplies were a must!! Although I no longer to back to school, I could always use some new work clothes!
school shopping was always boring for me as I went to Catholic school and had 2 older sisters so most of the time I got there hand-me-downs boring. I always wanted to go shopping for new school clothes with cute shoes
Would really love a new backpack for travel!
I used to love picking out all my new folders and of course the Trapper Keeper! My little could def use a backpack this year!
My grandma would always take me shopping for back to school clothes, and I always assumed it was because my mom didn’t have the money to take me, herself. Now that I’m older, I realize that while that was part of the reason, but it was also just as enjoyable for her as it was for me. As a Momma myself, I always enjoy taking my girls shopping for clothes, shoes, school supplies, etc. I can only imagine how much fun it’s going to be to be able to take my grandkids shopping for stuff. <3
For some reason I used to LOVE getting new school supplies. It was the nerd inside coming out I guess! I’m actually starting grad school in the fall, so the gift card would be great to pick up a couple pieces to add to my closet!
My fav story is when we were kids we’d each have a certain amt of money to spend. One year I fell in love with a long sleeve silk blouse and a green velvet skirt, and fancy shoes. It was at an expensive store and it ate up my entire amount for shopping for the new school year. I remember wearing it every day, the hot early sept. days etc. When I look back I’m surprised my mom let me, but I’m glad she did, as was still happier than having a closet full of clothes with that one outfit! We have a Sears nearby, I’m lucky! and I love shopping there!
I could use some new jeans and tops!
I always loved back to school shopping as a kid, especially the shoes and school supplies! Had to get my nice bright white new Keds and a new Trapper Keeper! This year I need ALL the things since I will have three kiddos heading off to school in a couple of weeks.
school supply shopping is the best! But I remember one year, after many stops, I just could NOT find the perfect sneakers! So, I ended up buying white Keds, and then dyeing them teal with my mom… And completed the look with hot pink shoelaces :)
I’m hoping to land my first elementary teaching job this year and could use some new cardigans!
I loved shopping for a bookbag. Everything else we had to choose certain colors from the list. We went to a catholic school, so we didnt have much variety.
My little one will be starting daycare this fall and I’d love to do some back to “school” shopping for her.
I’m needing some new shoes, flowy shirts, and jeans
I could definitely use some new jeans this fall!
Baby #2 is due in October! I would love to pick up some matching sister outfits this season even though neither babes are headed back to school yet! :-)
I remember getting a new trapper keeper before school started. This is dating me big time.
I remember going to the uniform store every August with my brother and sister to get our school uniforms. This was usually a day long process because the embroidery machine was always an hour wait.
I would definetly start on the school shopping with this!
I would like some new dress slacks.
I also had the opportunity to back-to-school shop with the grandparents. My grandmother had previously worked at Sears and she and I would always go there to shop.
I would buy uniform tops and bottoms for my niece , who start s full day Pre K in August!
I remember shopping for the new styles with my mom and dad and being so excited to wear them during the first week of school!
I always absolutely looooved shopping for school supplies!! Still do, actually. And every year I’ll get caught up in the “back to school” excitement and buy a bunch of new pens and stuff even thought I’m not going back to school anymore.
My favorite back to school story is really more like a tradition. Me and my BBF (still to this day) would go back to school shopping and get a matching t-shirt every year! <3
I’m always looking for new shoes, back to school season or not! :)
the time my dad took me for back to school shopping was special to me. I still need everything for my daughter before she starts pre-k.
New jeans are much needed around here (and new shoes are always wanted haha)!
My kids are funny about this. The boys dread it but my daughter who’s three loves it. She wants to buy a backpack like her brothers. We could use any help we can get with school supplies/clothes this year.
One item I need is a new laptop.
I have a toddler as well … But I teach so I do have summers off and it will be a “back to daycare” situation for her, too :) I’d love to get her some new shoes … Her feet grow so quick!!
I remember one year I took my daughter to outlets for school shopping and she got brand name jeans and they fell apart first time I washed them!!!
Even though I don’t have kids, I’m a teacher so back-to-school shopping is still a thing for me :) I’d love some new dresses to start the year!