His & Hers / Jack Rogers Giveaway!

This week’s His & Hers feature is particularly exciting because it ends with a giveaway with one of my all-time favorite brands! Check it out and pay close attention to the sandals 😉
Like my new sandals? I sure do! That’s why I’ve partnered with Jack Rogers USA to give one lucky reader her own pair of monogrammed sandals! To enter, please leave a comment telling us how you’d wear your new sandals this spring.

For extra entries, please do the following and leave a separate comment each time for a maximum of four total entries:
1. Like Design Darling and Jack Rogers on Facebook.
2. Follow Design Darling and Jack Rogers on Twitter.
3. Follow Design Darling and Jack Rogers on Pinterest.

The winner will be announced on Friday morning. Good luck!

773 thoughts on “His & Hers / Jack Rogers Giveaway!

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  1. Omgosh I love Jack Rogers. The question is what wouldn’t I wear my Jack Rogers with. I think they will go with my jeans and white t-shirts to my summer skirt and tops!! I liked you and Jack Rogers on FB and I am already following you on Pinterest and now I am follow JR too!! Fingers crossed,
    Kathysue

  2. I’m traveling all summer, I would love to own my first pair of Jack Rogers after having loved them for so long. I would take my pair all over the country with me, they would go cute with every outfit I wore and they would get to comfort my feet in my journey around the country. I would wear them with my favorite Lilly dress to start with, after that who knows!

  3. The real question should be: What would you NOT wear your monogrammed Jacks with?
    The only times you’d find me without monogrammed Jacks on would be when I’m playing soccer (sort of hard to run in sandals!) and when I’m sleeping.
    I’ve been obsessed with monogrammed Jacks since they came out, but never had enough money to spoil myself with a pair. I can already envision numerous outfits I’d love to wear monogrammed Jack Rogers with. From maxi dresses at the beach, to a pair of white jeans and an off-the shoulder top. The list goes on and on.
    To sum it up, winning this pair of Jacks would make me the happiest girl in the world!

  4. Jack Rogers are my staple and are worn everywhere from the law office on casual Fridays (and inevitable walks to and from the courthouse instead of heels), Saturday date nights, trips to the beach, and as a Floridian pretty much year round. I have been DYING for a monogrammed pair and it would complete my collection!!

  5. I’d wear my monogrammed Jack Rogers to all the fun activities this spring, from Mommy/Daughter day for my sorority, to the Kentucky Derby!! I’ve always wanted Jack Rogers, and these monogrammed ones are by far the cutest!! Pick me!!

  6. I would style my sandals with cropped jeans, a plain white tee and a matching cardigan. I would also load up my wrists with a watch and tons of bracelets and finish the look with oversized glasses and pearl earrings!! such a classic look for a sandal that needs all the attention.

  7. I love wearing sundresses with my jacks but I cant afford to buy a new pair so they have been getting a little worn out. Id wear my new sandals with EVERYTHING! Jacks go with everything so it would not be a problem!

  8. I love Jack Rogers! I would rock mine with a Lilly dress and my Ray-Bans at the Kentucky Horse Races (Keeneland, the Derby)! I would also wear them to work with a frilly skirt from Ann Taylor. Actually, I would wear them all the time! (:

    Also, I’m following you on Twitter and Pinterest and Jack Rogers on Twitter!

    LOVE!

  9. I would wear my monogrammed jack Rogers all the time. I would wear them when dressing up for sorority events or just lounging in everyday clothes. I usually wear Nike shorts and a Dphie t shirt so I would totally wear monogrammed jack Rogers every where and with everything

  10. I have always wanted a pair of monogram Jack Rogers and I love the navy and white pair you are modeling! I think they would be so cute with anything from bright colored jeans, white skinny jeans, or any nautical dress! A must have for spring & summertime!! 🙂

  11. A new pair of Jack Rogers would go perfectly with my white jeans and various tunics so I stay cool and cute for spring and summer 🙂

  12. I’d rock these babies basically every morning this spring and summer! Walking in heels is a hazard around Boston and those flats are just what I need to navigate the T like a seasoned pro! Plus I’d be able to use my new married monogram, double bonus!

  13. I love your blog! AND have always wanted a pair of Jack Rogers!! I would wear them to the hospital for my 3 year check up for my stem cell transplant!!! What a “birthday” gift!

  14. My friends tease me with my monogram obession so clearly monogram jacks have been a staple in my closet for years. I love mixing my classics with current trends. throw a navy striped cotton shirt, black ankle pants and a turquoise statement necklace and my orange jacks of course!

  15. I am following both Jack Rogers and Design Darling on Pinterest!

    I desperately need some dressy causal shoes so I would wear them with skirts and dresses!

    Thank you for the giveaway Mackenzie!!

    Ashley Munoz

    ashleymmunoz@gmail.com

  16. I would wear them with EVERYTHING in my spring and summer wardrobe! They are so classic that they go with everything – I will have a hard time finding something not to wear them with!

  17. oh you are thinner! I guess you are being healthier 🙂
    those are so pretty sandals! I would wear them with skinny jeans and sheer shirts!

  18. Seeing as how it is flip flop season almost all year long where i live… i’d wear them with jeans, cute skits, scalloped shorts… the possibilities are just ENDLESS!!!

  19. I would wear them all summer long with colored cropped pants, and scalloped shorts! They are perfect for all of my new england summer travel to Newport, the Cape and Nantucket!

  20. Stuck in the dry, Phoenix heat all summer long, these pair of Jack Rogers, a coveted item that I long to add to my wardrobe, will add some preppy flare to my traditional-southwest style. As a teenager, I find it hard to buy these highly priced staple clothing items, and I find this a perfect opportunity to try to integrate these into my closet! 🙂

  21. Wow! There are so many things I would pair these with! For starters, my new skinny jeans! And of course I would wear them with my Lilly dresses, new chino shorts, and I would definitely wear them all over Europe when I go for a month this summer! I would show them off to everyone over there!

  22. I would wear my new jacks with just about anything:) a perfect day in mine would consist of coral shorts with a cute white cable knit sweater-it is still pretty cold at bucknell in the spring time!

  23. I love my gold Jack Rogers and my brown ones… if I won this contest, I would definitely rock a brighter pair with my monogram. I’d wear them with all of my Lilly clothes, white jeans, and the myriad bright colored tops that are popping up in my closet for spring and summer. xoxo

  24. If I won, I would wear my monogrammed Jack Rogers with EVERYTHING! They are so classic and cute, how could you not want to wear them all the time?! I follow you both on Facebook, Pinterest, and Twitter, and LOVE everything you have posted (:

  25. The beauty of Jack Rogers sandals is that they can be worn with anything! For that reason, it’s most fun to buy a terrific color so you can jazz up a pair of plain khakis or complement a fun summery outfit. A definite go-to shoe for summer!

  26. I love the silver and jack rogers! They look perfect with skinny white jeans and just about any bright colored top!

  27. I would wear my new monogrammed Jack Rogers to fraternity and sorority band parties, baseball tailgates and games, and pretty much everyday to class!

  28. Those sandals are amazing! I leave for Italy in a few weeks, and they would be a perfect pair of shoes to travel the country in. They’d look great with my new skinny jeans or new Cynthia Rowley sundress. 🙂

  29. I love Jack Rogers & love wearing them with everything from my Lilly dresses to colored skinny jeans & a sheer top or even just shorts & a t-shirt…they’re the perfect shoes for any occasion!

  30. Well- before I go ahead any buy a pair for myself! Figured I would give this a shot. I would love to wear them with all my sundresses!
    I follow design darling and jack rogers on pinterest.

  31. Following you on Pinterest, Following Jack Rogers on Pinterest and Twitter. (already follow you)
    I would wear my Jack Rogers at the office (we are super casual) with some skinny cropped jeans and shorts; everyone would be jealous! SO cute!

  32. Oooh! I’d love to pair these with some white denim and a fitted linen shirt with sleeves rolled up and grandmothers’ gold bangles! Congrats on your success, btw!

  33. I’d wear a pair to anytime I need to look my best! Nothing says best dressed like a pair of monogrammed Jacks!

  34. In the spring & summer, I wear my Jacks constantly! Regular sandals cannot hold a candle to my Jacks. I wear my Jacks commuting to work every morning & evening with my J.Crew colorful pencil skirts and flowy blouses. I think it’s a fun, quirky way to get another pop of color into my outfit and a cute alternative to ballet flats.

  35. I would give my wonderful friend – a bride-to-be OBSESSED with JAck Rogers – the pair to wear at her wedding in July (with her new initials) when she hits the dance floor!

  36. Oh my goodness I have just been dying for a pair of monogrammed Jacks since I first saw them. I would wear them with what has been dubbed my spring uniform: khaki skirt, bright polo shirt, navy cardi, and a VV belt. What an amazing giveaway! xo, LP

  37. I would wear monogrammed Jacks with anything and everything! I can certainly see them as a staple in my wardrobe. I would wear them with a colorful tank top and white jeans for a girls night out with my girl friends. I would also wear it in the daytime in a more casual look with colorful shorts and a simple white t-shirt.
    I liked Design Darling and Jack Rogers on Facebook.
    I follow DD and JR on twitter.
    I follow DD and JR on Pinterest.

  38. I love my pairs of Jack Rogers that I already own, and would wear my monogrammed pair with everything from bright shift dresses, to white pants and colorful blouses, to chino shorts and v-neck cotton shirts.

  39. Love this giveaway! To be honest, I’m preggers with my first child so I’m not quite sure what I’ll be wearing this summer. I guess it just depends on what will fit! These sandals will fit though and I promise to wear them with style if I win!

  40. Ah I LOVE these! I’m pregnant with our first and these would be the perfect accessory to make me feel “cute” this summer with the bump!

  41. I’d wear these adorable sandals to my grad school graduation – which happens to also be Mother’s Day, and my father’s birthday! I can’t think of a occasion more in need of some adorable footwear 🙂

  42. I would wear my Jack Rogers every chance I could – with white jeans and cute, bright tops, with dresses and skirts (probably from Lilly Pulitzer), on cooler nights with warm sweaters and my favorite pair of jeans…I’d wear them with everything!

  43. Jack Rogers are a spring/summer staple in my closet- but adding the monogram ones makes them that much better! I would wear them with everything from chino shorts to sundresses!

  44. I would wear my new jacks to my high school graduation! and basically just about anywhere

    (I am following both Jack Rogers and Design Darling on Twitter as well !!)

  45. Jack Rogers are my favorites! If I won the monogrammed ones, I’d wear them with my favorite Lilly tunic (it’s a beautiful orange and a hand-me-down from my sister) and my white jeans (almost in season!)!

  46. Jack Rogers are my favorites! If I won the monogrammed ones, I’d wear them with my favorite Lilly tunic (it’s a beautiful orange and a hand-me-down from my sister) and my white jeans (almost in season!)!

  47. I would wear my Jack Rogers with EVERYTHING! But in the springtime I live in shorts and tees and a cardi for the breezy nights and those monogrammed sandals would be the perfect addition!

  48. How stinkin’ cute!! Te answer to how I’d wear them is “with everything!” Every Southern girl needs a monogrammed piece to complete her outfit.

    I also like and follow you both on facebook and pinterest.

  49. I also follow Jack Rogers and Design Darling on Facebook and Twitter! I also follow Design Darling on Pinterest! My comment is the same Kate as above!

  50. I currently have the silver and baby blue Jack Rogers! I would wear the monogrammed Jack Rogers with a plain tee and some colored jeans (red, green, pink, etc.) Navy monogrammed Jacks are the perfect way to exercise with most outfits. I mean, who doesn’t love the nautical or classic look?

  51. I am following Jack Rogers on pinterest! My username is pinterest.com/allicatsplat

    I would be so thrilled to be an owner of these sandals & would rock my NEW monogram (I am getting married May 19th) on a beautiful pair of Jack Rogers custom monogrammed sandals with skirts, jeans, shorts, dresses – any and everything!

  52. I am following Design Darling on pinterest! My username is pinterest.com/allicatsplat

    I would be so thrilled to be an owner of these sandals & would rock my NEW monogram (I am getting married May 19th) on a beautiful pair of Jack Rogers custom monogrammed sandals with skirts, jeans, shorts, dresses – any and everything!

  53. I am following Design Darling on facebook!

    My facebook username is Allison Renfro

    I would be so thrilled to be an owner of these sandals & would rock my NEW monogram (I am getting married May 19th) on a beautiful pair of Jack Rogers custom monogrammed sandals with skirts, jeans, shorts, dresses – any and everything!

  54. I would wear them with a pair of capris and a polo shirt-taking that outfit from my casual office to a night out at the movies or dinner with friends!

  55. I am following Design Darling & Jack Rogers on Twitter!

    twitter.com/spacetorun

    I would be so thrilled to be an owner of these sandals & would rock my NEW monogram (I am getting married May 19th) on a beautiful pair of Jack Rogers custom monogrammed sandals with skirts, jeans, shorts, dresses – any and everything!

  56. I would wear my Monogramed Jack Rogers to sit outside at one of my favorite wine bars this spring. Perfect addition to any outfit!

  57. I would wear them with SO many things! This s/s I’m loving them with a bright ankle pant & crisp white top. Classically chic, just like Jack Rogers.

  58. I’m a Florida girl, so I am very blessed to wear my Jacks 365 days of the year hence why I need a new pair they are getting a bit aged from all the wear :).

  59. Jack Rogers are a summer “must have” here in Charleston, SC. I love the navy color! I can see them being fabulous with a pair of white j crew shorts on the main deck of a sail boat on a perfect summer afternoon. Nautical bliss!

  60. Love my Jack Rogers! Having recently moved from preppy Boston/Nantucket to a suburb west of Chicago I love that people actually ask me where I got my shoes! Too funny as it’s such a staple of my wardrobe being from New England 🙂 I will wear them all summer and have always wanted the monogram ones!!

  61. I have lusted after these for YEARS and the day they come into my possession I will strut them proudly down the sidewalks of new york paired with my J. Crew scallopped bottom shorts, tucker top, and a big beach bag… they’ll be a weekend staple!!!

  62. I’d wear a pair to Keenland and the Kentucky Derby! Nothing says horsing racing best than a fine pair of Jack Rogers!

  63. I liked both pages on facebook, followed them on pinterest, and followed them on twitter. I would wear these with my new colored chinos from J. Crew and all of my bright Lilly Pulitzer shorts and capris! I have been eyeing these shoes for a long time and already love the silver Jack Rogers I have.

  64. How wouldn’t I wear these sandals is the question. I think they would easily be my go-to shoe. The outfit I’m dreaming of right now involves white skinny jeans and a gingham button down with a straw fedora.

  65. Jack Rogers, especially monogrammed ones, are a closet essential. What wouldn’t I wear them with? Everything from a simple sundress to a pair of jeans and a cute top. My ultimate favorite would be pairing them with my newly purchased neon pink shorts an a light blue button down, preppy perfection!!

  66. I would wear these darling monogrammed Jack Rogers while I’m studying abroad this summer in London. Nothing more perfect than a pair of Jacks to wear everyday while traisping through Covent Gardens, or out for a cappucino.

  67. I would wear these darling monogrammed Jack Rogers while I’m studying abroad this summer in London. Nothing more perfect than a pair of Jacks to wear everyday while traisping through Covent Gardens, or out for a cappucino.

  68. I like both Design Darling and Jack Rogers on FB!

    I forgot to mention this would be my first monogram with my married name so would wear them happily everywhere I go 🙂

  69. I live in my jacks in the spring and summer. I see myself in the monogrammed jack rogers paired with maxi dresses and colored ankle skinnies… loving the navy and white that you have. Very classic, Jackie O chic.

  70. Moving back to CT this summer after being away the past 10 years, could definitely use the perfect shoe addition to add a little more “prep” to my outfits.

  71. I love Jack Rogers (and not just because that used to be my last name as well). White jeans, cute dresses, summer weddings…I’d defintely wear them as much as possible and I think they could be totally work appropriate for the Bucknell Career Center in the summer! 🙂

  72. I would bring my new Jacks paired with my favorite Lilly shifts on an International adventure this summer.

  73. Oh gosh! I’ve wanted a pair of these for AGES! I think I would best style them with denim shorts and a polo. Keep the top simple to let the shoes take center stage (as well they should!).

  74. Since I’m potentially moving to Brazil for the summer, I’d wear them with everything to bring a splash of southern summers into my South American summer!

  75. I’d wear my Jack Rogers with all my J.Crew chinos and sundresses. They would look adorable with everything!

  76. I absolutely ADORE Jack Rodgers!! They’re without a doubt my favorite shoes and I wear the current pairs I own everywhere! This spring I would be pairing them with white jeans and probably my favorite navy-and-white ikat top!

  77. I would wear my Jack Rogers with a cute pair of rolled up jeans and a cute with tank and a very springy sweater… for the hotter spring days pair them with some cute lilly shorts and shirt!

  78. I think I would wear mine to many summer weddings as well! No uncomfortable heels for this tall girl 🙂 Keeping my fingers crossed for a pair of these adorable sandals!

  79. I love the Jack Rogers sandals that I own, but I am just dying to add a monogrammed pair to my collection. Jean shorts and a polo would make a lovely, preppy combination!

  80. I Love Jack Rogers!! Such a classic, timeless brand that I wear all spring and summer long. I love wearing them with my Lilly dresses and skirts especially!

  81. How cute! I would definitely wear these to my sorority formal because I can’t stand heals! But, let’s be honest, I would probably wear them everyday as well! I have also liked/followed both Jack Rogers and Design Darling on FB, Twitter and Pinterest 🙂

    -Annie

  82. I love my Jacks and have been lusting over a monogrammed pair! I would wear them with everything; shorts, skirts, dresses, but especially my white skinny jeans!

  83. I have three summer weddings on the horizon- being a newlywed myself, I’d love to have a pair of these babies with my new initials!

    captivetheheart.blogspot.com

  84. These are adorable! The monogram is the perfect touch 🙂

    I would wear these all spring and summer with everything from my J.Crew chinos to my Nantucket Reds to a pretty little sundress. These sandals are so versatile and absolutely darling!

  85. Sorry doing them separately now:I booked a trip to Italy yesterday and I can dream of wearing these on the amalfi coast on all the cobblestone streets. What perfect shoes they would be:)

  86. 1. I follow design darling and jack rogers on facebook.
    2. Don’t have twitter:(
    3. I follow design darling and jack rogers on pinterest which is super addicting!

    I booked a trip to Italy yesterday and I can dream of wearing these on the amalfi coast on all the cobblestone streets. What perfect shoes they would be:)

  87. I think a more appropriate question would be how wouldn’t I wear them this spring? I have a few pairs of the Navajo style and I wear them EVERYWHERE! I imagine I would wear these monogrammed beauties everywhere too 🙂

  88. I love Jack Rogers. I would wear the monogrammed pair with Lilly and J.crew dresses. They are a wardrobe staple when you live in Palm Beach.

  89. I think the real question is how would I NOT wear these sandals? I would live in Jack Rogers all spring and summer, and since I live in Texas, probably all fall too! 🙂

  90. I love these Jack Rogers sandals! Sandals are a summer staple of my wardrobe of shorts & dresses, and with the monogram you can’t get more southern!

  91. I actually just got my very first pair of Jacks this Friday and I already love them. I would love to wear the monogrammed pair with a pair of chinos and a button down/oxford! 🙂