The End of Gossip Girl

{Images from Blair Waldorf Fashion} Gossip Girl is over. Granted, Gossip Girl has been over for a few weeks now, but I just saw the finally. Gossip Girl is one of the few shows I’ve watched from the beginning until…

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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Blazer urban outfitters (old), Sweater unknown brand,  forever 21 jeans, City Classified boots For Christmas my parents gave me these gorgeous boots! I’ve already used them for a few outfit ideas on the blog and now I can really wear…


  • A little snowy magic in NYC today ❄️ Not mad it’s supposed to melt overnight though 🙈 Anyone else counting down to a warm weather vaca?!? 🌴
  • Missed the first 20 minutes of the bachelor and now I’m so lost 🤦🏽‍♀️🌹 Anyone else watching tonight? Seriously hoping tonight will be the night he jumps over the fence 😂
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  • Easy like a Sunday morning 🎶 Went for a long walk with @ahhlee11 and stopped by my favorite bagel spot this morning 🥯 Couldn’t have asked for a better Sunday ✨
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  • Happy Valentine’s Day! ❤️💋 Anyone else have a permanent sugar high after all the sweets today? 🧁
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  • Hiding out from winter with my summer hats & photos from warmer times ☀️I’m the worst kind of person who loves snow in January but by February I love to hate it 🙈❄️ Anyone else understand?
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Merry Christmas!

{photo on my tumblr} Merry Christmas to all! Today I’m spending time with my family in Connecticut. I’ll be eating plenty of good food, relaxing, and taking lots of pictures. I was already given some incredible presents from my parents…

After Christmas Sales

blouse, pants, dress, blouse Top Row: necklace, shirt, tshirt Bottom Row: bag, skirt, vest So I know it isn’t Christmas yet, but my mind is already fast forwarding to the hundreds of after christmas sales that I will be searching…

Christmas Day Statement

{Images via Stockholm StreetStyle} Jeans: Forever21, BDG, Acne, JBrand Tops: Nordstrom, Madewell, T Babaton, Miss Selfridge Shoes: Aldo, Chelsea Crew vis Urban Outfitters, PROSA, Aldo As Christmas day approaches I have been thinking about what I will be wearing to…


{pictures from my trip to New York in September} wearing: Gap jacket (outlet), topshop peplum shirt, zara jeans, aldo flats Hey all! This week is my last week of school before winter break and my teachers have decided to cram…

Weekend Finds

clockwise from top center:  topshop dress, topshop dress, J.Crew hoodie, PROSA booties, topshop booties, madewell bag, Urban Outfitters headband, Madewell gloves, J.Crew jeans It is snowing in Massachusetts today! I’m not a huge fan of snow but it is still…

Thank God It’s Friday

{images from my Tumblr} Seriously. This week could not have been any longer. I’m so happy it is the weekend! I’ll be running around looking for Christmas presents since I haven’t bought any. I have a long list of people…

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