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I decided to wear some thrifted finds to a family dinner last Sunday.  My sister-in-law said, “You’d make a cute jockey.”  And a blog post was born!  Thanks K*!

jacket: thrifted Ralph Lauren {similar} // sweater: thrifted Marc Jacobs // leggings: UNIQLO // socks: UNIQLO // bag: gifted Dooney and Bourke {similar} // boots: Alex Marie {similar} // sunnies: Karen Walker

I couldn’t resist posting that last picture.  It reminds me of Willow Smith’s “Whip My Hair” song! LOL!  Some outfits are all about the details.  I really love the little bow on the neckline of the sweater.  And the plaid and ticket pocket on the jacket are so fun – maybe equestrian or grampa chic!  Either way, it still made me happy to wear it!  And both thrifted pieces being less than $30… well, you can’t ask for more.

Happy Monday Lovelies!  Do you wear plaid blazers?  And what do you wear it with?

{Bloglovin | Twitter | Facebook}

Read the Comments +

  1. Mica says:

    You are so pretty, more like a model than a jockey! Love the inspiration though, such a classic relaxed outfit that blazer is perfect for it! :)

  2. gorgeous look hun! that jacket looks adorable on you :)


    Fashion Fractions

  3. Aline C. says:

    hahaha you WOULD make a cute jokey! Adore the jacket and the boots.
    and now I have that Willow Smith song stuck in my head :P

  4. Love the thrifted jacket Sam, it is so pretty! And of course looks great on you :)


    P.S. Thank you so much for the belated birthday wish, you are so sweet!!!!

  5. Leticia says:

    LOVE this! Those angle pockets on the jacket are such a nice touch!

  6. Jenna Hughes says:

    i love the 70’s influence! those glasses are awesome

  7. HAHAHA – you whip your hair so well! I have been on a search for this particular plaid jacket at h&m but they never have my size. I love yours! Very chic. Don’t you love it when you get inspiration from a family memeber’s comment =)

    Happy Monday =)

  8. Lemiza says:

    You look gorgeous! I’m in love with the jacket!!!
    Have a nice Monday!


  9. pjlatte says:

    What a cute post! and fabulous finds!!

    Visit me & my bags, shoes, and all things dainty at: or on Bloglovin’

  10. Sayaka says:

    haha…whip your hair!! You look so beautiful!! The blazer is awesome!!

  11. steph says:

    nice finds, love the blazer especially even though it’s not quite my style – the tailoring is beautiful and i love the socks peeking out. You do look a little like a jockey, a cute one :)

  12. I love this equestrian inspired look! Your boots and jacket are fabulous!

    See Me Rwar

  13. You have fantastic hair and it looks great pulled back too!

  14. Jen @ redsolesandredwine says:

    That’s a fabulous equestrian inspired outfit – and what a deal for less than $30 for the items.

    Your hair is getting so long, love it in a pony!

  15. Mary Ann says:

    What fabulous thrifted finds – you can tell how nice the jacket is by the way the plaid stripes are so well matched seam to seam!

  16. Carolyn says:

    loving those tortoise sunglasses!

  17. Nini says:

    Nice, looks really comfortable!!

  18. WHIP that hair girl! HaHaHa Your outfit looks so refined and distinguished Sam! If you were in a race, I would definitely bet on you. That’s a great blazer. I love the collar and pockets. Love the little bow on your top and of course your boots. Exquisite girl! :D

  19. Alyssa says:

    You belong at the Hampton Classic. Love this outfit to bits…no pun intended :)

  20. Katrina says:

    My knees went weak when I saw this photo. I have a severe love and weakness for any jockey/equestrian/riding look. I think it’s super chic and elegant. Wow…love love love!!!

  21. Rocker Chic says:


    You make a cute jockey I love every detail of this outfit and although I don’t own a plaid blazer you’ve inspired me to def get one.

  22. I really enjoy reading your blog posts!!!! If you have a chance, please visit/follow my fashion blog. It will mean the world to me if you did. Thank you so much in advance!!!

  23. Annie says:

    How gorgeous is this outfit?! I LOVE it Sam…that blazer, the sunglasses – you look fabulous :)

    The Other Side of Gray

  24. Melody says:

    Indeed…you look like a jockey ;p

  25. Cara says:

    I was going to ask if those were Karen Walker glasses cause they are so fantastic! I love this look, can’t believe you thrifted this amazing blazer and top. Love the purse too, you look ready for Aspen in Fall!

  26. I love this! I don’t have a plaid blazer but now I am starting think that I may need one :) does my houndstooth version count?

  27. Nelah says:

    Your sister in law was absolutely right. Your outfit says ” jockey” inspired out loud and in a good way. Like how preppy and fun you look. I think a pair of white shorts would look great with this blazer too.

    Forever21, i know right. They are becoming more and more ridiculous with prices and quality. I said bye bye.

  28. This is a popular look here in my neck of woods. You’ll fit right in! Love the outfit.

  29. Camilla says:

    Love the boots, the jacket and the bag!
    Amazing items!

    Camilla /

  30. I love this. Maybe I can wear my tweed jacket like this too!!! And I remeber that Dooney and Bourke purse when it first came out!

    7eventh Letter

    • Samantha says:

      I was in middle school when D&B bucket bags were totally the thing!! I really wanted one but they were WAY TOO EXPENSIVE!!! I was super psyched when my MIL gave it to me {from her mother}!! It took me back to the 80s!! :)

  31. I like this! So timeless you could be in 1920 or 2012. Great look!

  32. oh sam, i love this look. very smart and stylish!!

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Hi, I'm Sam

Your new internet friend, Accessory Advisor, and advocate for self-love and confidence.

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