We’re giving away four pairs of sneaks, sponsored by Sears

by Whitney on January 18, 2012

My go-to fancy outfit for little boys who don’t need to own dress shoes is a pair of clean Chuck Taylors with khaki pants and a dress shirt. This summer, we had a wedding to attend, and I bought Julian a pair of slip-on Chuck Taylors for the occasion. I didn’t let him wear them until the event, so they were sparkly and crisp that day, and then they became his everyday shoes for the rest of the summer. If I’m in charge — and so far, I am — he will probably grow up without owning a pair of leather shoes until he goes to a job interview.

So, when I was contacted about Converse shoes at Sears.com last week, I said, “Heck yeah, you guys can sponsor a giveaway!” I personally love Converse on kids and adults, including moms. And on toddlers? The cutest! Right?

If you’ve got time for video, here’s a tour of the product line available at Sears.

I asked my contact on the Sears team if I could let our giveaway winner select up to four pairs of shoes to outfit her family. (Sorry, larger families!) Here’s what I’d pick, but you can make different selections:

For myself, as much as I am drawn to all the colors of the low-tops, I’m tempted by the cozy boots. Today I’m wearing a grey tunic over black leggings with boots exactly the same height as these, but not nearly as comfy looking.

For my husband, who already has black Chucks, I’d go for the stripeys.

For Julian, age 7, I’m digging the mid-profile shoe in olive green.

For Scarlett, age 4, I can’t decide between going all the way with this red gingham or the navy version that just features the gingham on the tongue. Her birthday is on the 4th of July, so she is partial to the patriotic look. I think the gingham will be cute with shorts during the summer.

Okay, here’s your chance to win. Just share a brief description of the outfit you’d pair with a new set of Converse sneakers for yourself. On Wednesday, January 25, 2012, I will select a winner at random to receive four pairs of Converse from Sears.com. Giveaway rules here.

Thanks to Sears for sponsoring this post — and thanks to my mom for not saying ~~anything~~ much when I wore pink Converse high-tops with a white sundress to my high school graduation ceremony.

a d v e r t i s e m e n t

{ 118 comments }

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Lisa K. January 18, 2012 at 6:18 pm: I was thisclose to buying a pair of wool ones online for myself last night!
Temps are plummeting here in Chicago this week, so I’d wear them with warm sweater tights, a skirt, shirt, and sweater, and my long down coat (from Lands’ End, Sears peeps! *wink*)
Tiffany January 18, 2012 at 6:33 pm: I would wear them daily! Jeans, long sleeve T’s, tanks, you name it! I wore a personalized pair for my wedding – turquoise and red. Sadly, after having my son – who stretched out my feet – they no longer fit. As for my son, a pair of slip ons would be fantastic everyday shoes. My husband would want to go old school with plain black hi-tops!
Jess Collins January 18, 2012 at 8:07 pm: I would love a pair for our DD as she is a shoe diva already! a cute pair of tights and a sweater dress in the wintertime, and during the summer they look great with a fun tee and khaki skirt!
Stacy January 18, 2012 at 8:40 pm: Great contest, thanks! I’d wear jeans and a nice t-shirt with my Converse.
Emma January 18, 2012 at 10:05 pm: The navy lady all stars with a pair of skinny jeans and a really dressy top… just seems fun to wear casual with dressy
Miranda January 18, 2012 at 10:31 pm: I love Converses with skinnier and a cute sweater.
Denise January 18, 2012 at 10:41 pm: Jeans, tshirt and jacket. My go to outfit needs a new go to pair of shoes. It might be boring but at least i am ready to chase after my baby!
Elle B January 19, 2012 at 12:16 am: Can these be our shoes for the 7 style resolutions? If so, then I’d go with my cute jeans and “unusual” tee combo and add in some super fun shoes!
Katy January 19, 2012 at 1:31 am: for my 2.5 year old the ideal outfit would be pairing the cool sneakers with khakie knee length shorts and a polo shirt in green
Sharon M January 19, 2012 at 3:53 am: My summer “uniform”: Capri length jeans and a tank. And I would loooooooove a tiny pair for my little man’s first birthday this summer!
Jessica M January 19, 2012 at 5:42 am: I love my Chucks! I especially enjoy pairing them with a “nice” outfit. It always gives people something to question about my wardrobe.
MV January 19, 2012 at 6:15 am: I would love a pair of white or brown Chucks to wear with jeans and a sweater!
Brie January 19, 2012 at 6:22 am: I would love a pair of basic gray slip on converse. I would pair it with my fave jeans and at-shirt.
Taryn January 19, 2012 at 6:25 am: I live in snowy Wisconsin so I’d wear that boot with EVERYTHING: jeans and a sweater, a big coat, hat and mittens. Oh, and my baby in the Ergo.
Stephanie January 19, 2012 at 6:31 am: Well I would love to pair them with my bridesmaid dress for my brother’s wedding but I’m pretty sure that wouldn’t fly, perhaps for the reception though? But in all seriousness they are just the perfect addition to the basic t-shirt and jeans, this time of year I would add a nice hand-knit sweater to stay cozy and warm.
Bre January 19, 2012 at 6:36 am: I’d wear those cozy boot ones with leggings and tights (and they’d get lots of wear here in MN!).
Susan January 19, 2012 at 6:40 am: I remember when my older sister wore one pink and one purple Converse sneaker in junior high, and I thought she was crazy.

I’d pair converse with anything my little one wears. Sneakers are definitely an everyday item for him. Even his “dress” shoes are sneakers.
carrie January 19, 2012 at 6:40 am: I’d get the pink lite slip shoes, and pair them with a denim skirt and tunic for spring. **hoping spring arrives soon in MN**
Valerie January 19, 2012 at 7:44 am: I’m looking ahead in anticipation of Spring! I’d pair them with jean capris and a cute top!
Jill January 19, 2012 at 8:44 am: I like them paired with some comfy worn jeans and a cozy turtleneck sweater – all casual of course. Can you tell it’s winter here, and I work from home, and like to be comfy?
Zuania January 19, 2012 at 9:11 am: I would wear them with jeans and a sweater. Fun!
rebecca January 19, 2012 at 9:45 am: Oooh…what fun! Is your son also wearing Ray-Bans? Too cute!

I’d wear some green ones with jeans, a puffy vest, and a long sleeve. I need something to brighten up that basic outfit.

Thanks!
Renee January 19, 2012 at 10:31 am: I’d wear some Converse with jeans and a puffy vest for a very casual look. Never tried “dressing them up” before, but maybe I’d have to try!
Jess W January 19, 2012 at 10:42 am: Love chucks!!! For the winter months, I would pair with jeans a long sleeve shirt and fleece vest!!
Gina January 19, 2012 at 10:57 am: My 3 yr old has acquired my shoe fetish -haha – I think I would make these his go to summer shoes – he hates socks!
Debbie January 19, 2012 at 11:36 am: Jeans, t-shirt, jacket, maybe in colours to match the shoes!
Sarah January 19, 2012 at 12:30 pm: My preschooler has worn a borrowed suit & tie paired with clean black converse for a wedding. He looked adorable! They were his “fancy shoes.”
Michelle Carter January 19, 2012 at 3:27 pm: I would wear my old navy jeans, a t-shirt and a baseball cap. The converse shoes would be perfect match for my casual day.
Tara V January 19, 2012 at 3:32 pm: Ooh, I love converse low-tops with cuffed boyfriend jeans and a comfy t-shirt in the spring. Fun giveaway!
Desiree Fawn January 19, 2012 at 3:34 pm: I’m pretty much Converse obsessed — my black lowtops are my standard footwear from Spring til Winter. I love wearing them with skinny jeans, a cute top, scarf, cardy combo.
Mama B January 19, 2012 at 4:26 pm: In a jeans & T gal, but I love funky footwear. I’d pick up the wildest high tops in stock and wear them out.
Kat A January 19, 2012 at 4:45 pm: I am a hardcore Chuck Taylor fan. I’ve lived in them since I wad 14. I’ve had too many pairs of Converse sneakers to describe but I’ve favored classic black canvas hi-tops over the years. The only downfall these days is tying them. Crazy, right? I find myself bypassing the laces of my Chucks in favor of the ease of slip on footwear in the chaos of being a new mom (baby girl born 11/25/11). So, if I were to get a new pair of converse, I’d go w/ the classic blacks in a lo-top slip-on. And the outfit I’d wear with them would be gray skinny jeans & a Threadless tee w/ a black cable knit cardigan.
Cara B January 19, 2012 at 5:13 pm: I would dress my son in his cute little cords and a comfy sweater. The Converse would just be so cute to add. For my daughter, a funky little dress with leggings would look so cute.
Liz Farrar January 19, 2012 at 5:19 pm: I like them with leggings, a cute top and blazer! Or Desiree’s outfit above sounds super cute!

My boy would wear them EVERY DAY. So cute.
Missy January 19, 2012 at 5:25 pm: LOVE the Converse brand!!
I would keep my outfit simple and neutral – dark wash jeans and a slouchy black t-shirt – and then pair with a bright colored lowtop such as the vibrant green!
Liz January 19, 2012 at 6:11 pm: I would love to pair the chucks with jeans and a comfy hoodie. I’ve been so busy chasing my one year old son, and he would look adorable in matching shoes too:-)
Liz January 19, 2012 at 7:43 pm: Jeans and a tshirt! Perhaps a cute scarf too.
Lauren January 20, 2012 at 5:08 am: My go-to outfit: jeans and the $8 target tee. So easy. Love those converse boots!
Brianne January 20, 2012 at 6:46 am: Since the weather is always pleasant in Phoenix, I would pair them with a comfy pair of jeans and a simple T shirt. I love the idea of having statement sneakers that make a simple outfit more exciting!
eme January 20, 2012 at 4:38 pm: I would love to have my twin boys wear these types of sneakers. Awesome idea.
Jamie January 20, 2012 at 8:43 pm: Jeans. Tee Shirt. This is all I wear! I would love to have some new shoes though! Thanks for hosting.
Jill NM January 20, 2012 at 9:36 pm: I have these olive green plaid pants I got in Paris a couple years ago and have never had the right shoes for them. All along I’ve just been wanting some good old black Chuck high tops, but, you know, when do I shop for myself?
Catherine January 21, 2012 at 6:24 am: I would LOVE this giveaway!

I love dressing my 2 year old in a cute pair of bluejeans a top/sweater and his red converse. He’s currently the only one who has chucks, AND he has two pair! (love the black high tops)
Toddlers ARE adorable in them, but who isn’t?
Angeles January 21, 2012 at 1:15 pm: My new sneakers would look great with tights and a conmfy skirt. T shirt and a vest on top!!!!!!!!
ellen January 21, 2012 at 2:10 pm: I’d wear them everyday- with jeans and a sweater, a tshirt, a tank..anything!
Julia January 22, 2012 at 7:27 pm: I wear Chucks with E-V-E-R-Y-T-H-I-N-G.
A new pair I would probably keep on reserve until my first (of MANY) Spring walks in that amazing sunshine that is juuuuuuust warm on your face. I’d pair them with a big scarf, my well-loved army jacket and big ol’ sunglasses. Can hardly wait for SPRING!!!
Jess January 23, 2012 at 1:56 am: I’ve been a long time fan as well. I’d wear them on the daily as well. Jeans, a tee, a sweater, they go with just about anything!
Helen January 23, 2012 at 2:27 pm: Hmmmm…jeans, solid tee, cute scarf…!
Monique January 23, 2012 at 7:01 pm: I’d pair those jazzy boots, with leggings, and a cowl neck sweater, that way I’d be oh so stylish, and mommy comfortable!
Jasmine January 23, 2012 at 7:32 pm: Chuck Taylors, classic Cali staple! I’d wear a white 3/4 sleeve button-up blouse w/low-rise skinny denims and Chucks to match my scarf in my hair For my 1 yr old son: a white tee and denim shorts w/chucks