Best Pieces of 2018

2018 has seriously flown by! I know everyone says that and we say it every year, but I have to say this year blew away all my expectations. I did a little year in review over Instagram over on Instagram…

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Hey There! I'm Caroline, the girl behind When & Wear and a 20-something trying to navigate life & style in NYC

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My Favorite Christmas Traditions (that you can start too!)

Over the last few years holidays have become even more special with my family now that my sister and I aren’t living at home. While Thanksgiving always seems like a whirlwind, Christmas gives us time to relax and actually spend…

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Instagram

  • Outdoor seating season is here 🙏🏼 AND GoT is tonight... couldn’t have asked for a better weekend .
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PS my top is under $20 and linked via @liketoknow.it #liketkit http://liketk.it/2B9NP
  • This has been the longeeeestttt week you guys 🤦🏽‍♀️ SO I’ll be spending tonight on my couch rewatching New Girl with some ice cream maybe 😂🍦 Who wants to join me?
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Shop this look via the @liketoknow.it app or at the link in my bio! 👏🏼 My shoes are also part of the @shopbop sale and I’ve been wearing them ALL the time! http://liketk.it/2B5Vs
  • Living like my phone is at 1% 📱(because it usually is 😂) #singlenotsorry #tinderpartner
  • That’s a wrap on my 2nd #rStheCon 🥂 I could sleep for a week after conference, but love getting to spend the weekend with this team 💕 #rSthefamily
  • Ciao Y’all 🍋🇨🇱 A phrase that only makes sense at a Amalfi themed party in Texas 😂 Had so much fun last night kicking off #rStheCon with @solesociety last night! .
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Shop my dress under $25 via @liketoknow.it or at this link 👉🏼 http://liketk.it/2AWN2 #liketkit #whenwearstyle

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Holiday Red Beret Styled Two Ways

This Christmas a red beret is the perfect accessory to make any outfit perfectly festive and it’s under $20.  Happy Friday! Can you believe we’re just a little over a week away from Christmas? I’m taking next Friday off so…

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Gift Guide: 40 Gifts Under $30

My favorite gift guide of the year is here – 40 gifts under $30 for your friends, family, and coworkers! Can you guys believe that Christmas is just two weeks away? Despite the early Thanksgiving this year, I feel like…

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Best Black Friday Sales

Happy Thanksgiving everyone! I’m writing this from my parent’s cozy living room surrounded by family and the smell of all our delicious sides cooking and I couldn’t be happier. Of course, these days we can’t even get through the beginning…

11 Piece Thanksgiving Packing List & Outfit Ideas

Can you believe Thanksgiving is only a few days away? If you’re headed out of town, I’ve put together the perfect 11 piece packing list for all your Thanksgiving activities from a dressy family dinner to lounging at home. I…

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London First Time Travel Guide

This post took me way longer to put together than originally anticipated, but here we finally are – My first time guide to London! Before this trip I was lucky enough to get amazing recommendations from friends who’ve traveled to…

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The 4 Best Fall Foliage Spots in Central Park

There is nothing prettier than Central Park in the fall and if you’re visiting New York City this fall there are a 5 spots you must visit to get the perfect shot. THE MALL If you’re looking for guaranteed gorgeous…

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Plaid Dress Two Ways

This fall I’ve been buying a LOT of dresses as opposed to skirts and it’s led to the tricky problem of trying to style them in more than one way so it doesn’t seem like I’m wearing the same outfit…

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Posts on WHEN and WEAR may include affiliate links, meaning when you buy products I recommend I may make a small commission. If you ever have any questions about affiliate links please reach out via email as I’m happy to discuss.