Casual Preppy Lookbook





Tommy Hilfiger White Blazer (similar here)  |  J. Crew Stretch Perfect Shirt  |  
Forever 21 Destroyed Denim Shorts  |  Chanel Bag  |  Miu Miu Flats (similar here and here)  |
J12 Chanel Watch  |   t+j Designs necklace and earrings

I was headed out to dinner with friends the other night and decided on a casual preppy look and yes, I am wearing flats!!  I only own a couple pairs of flats but these Miu Miu's have been my favorites for over 5 years.  They've moved with me from San Francisco to New York and now Chicago; my definite go tos when I need to walk around.  

This outfit is simple and I bet everyone has these combo's in their wardrobe.  A staple blazer, button down and some cute denim shorts, just add some jewelry and your ready to go out.  I am loving the weather in Chicago right now, it's cooled down a little, but perfect.  I don't want this weather to end!  Although I am ecstatic for fall fashions, I don't love the cold and fall means winter.  Hmmm, still trying to figure out how to show my looks come winter time :)!  Any advice let me know!

Don't forget about our lovely giveaway for beautiful jewelry!  Take a look at the awesome sets you can win HERE!!


  1. Obsessed.. especially the miu miu flats.. good to hear the weather in Chicago is nice right now.. I am supposed to be moving out there in October.. Like you, I am a California boy who also splits his time in NYC but settling out there for good.. WERK the look!

    Love! ~Angel

  2. lovely shorts and l also love the way you styled the rest of this outfit.

  3. Love this shade of pink, its not to sickly and paired with the white its so fresh!

    The doll on fashion

  4. Gorgeous! I love your necklace and bag. Thanks for following me. I'm your new follower:) Cheers!

    Fashion Cat

  5. I love to see you in flats those glittery are adorable, you rocked the preppy chic look!

    Cess O. <3 The Outfit Diaries

  6. Jen I love this look. In fact, today's a day that I can wear shorts at work so I might replicate this for our Cubs game outing.

  7. Perfect summer outfit!

  8. I like how you edited the first pic. So cool. THose ballet flats are so gorgeous.


  9. Jen,

    Love this outfit. I do have everything in my wardrobe to replicate this look. I just did't have the long legs. hehe.

    Now that you mention it, I am going to have a hard time taking outfit pictures soon since the weather is turning cold.

    Love your look, as always. ;)

    Love, Fashionandnumber

  10. Lovely outfit! I love the white blazer :)

    Lubna | ELLE VOX

  11. Unbelievably cute look! Love the colours together and the necklace is just beautiful!

    Girl about Town XxX

  12. You look so adorable in pink!I think this my favourite outfit!

  13. Yes! That blazer makes your entire outfit so smart and polished. And I recognize that necklace from your shop! :)

    <3 jen @ stuffjendid

  14. Such a cute look for the summer. I love your blazer!

  15. You look great! Love the blazer and the flats. That bag is awesome too.

  16. love that necklace and the flats as well :)

  17. You look stylish and beautiful as always! Love the white blazer!


  18. adore your casual preppy look jen!! those miu miu flats are GORGE!

  19. thumbs up! :) I love this look. and great job with the photos and the layouts. looks great!

  20. Love this look- the white blazer really off sets your pink shirt. I have been pondering over where I will shoot come winter time as well...alas summers end is near.

    Liv @

  21. simple and chic!the pink shirt is lovely and those flats are so sweet. i want them!

  22. Really love the white blazer - makes everything look so chic! And the Miu Miu flats are divine (makes me want to get more use out of mine)! Loving this casual preppy look!

    xo, sam

  23. Wow, you look amazing! This outfit is so stylish! Love everything about it, the white blazer, the pink shirt... I adore the bag!
    I'm sooo following your blog right now, follow me back if you like :)))

  24. I barely recognized you! I like the different look though. And I love the flats! Miu Miu always makes the best!

  25. those flats are a keeper then! haha you look so cute and different, lovely outfit :)


  26. very sweet outfit, love the pink mixed with the white! i love your blog <3

    now following you !


  27. Love the casual and classy outfit~

    I want skinny legs like yourssss~~!!! Haha

  28. Oh Jen you look adorable in this casual outfit!!!

  29. Your shoes and your short are so beautiful ! :O
    Love your blog.

  30. Love this outfit! I need more preppy inspiration like this - with a touch of glam!

    xx Vivian @


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