Street Style Jealousy

{Images from Stockholm Streetstyle} I think pretty much everyone wishes they looked like the girls shown on Stockholm Streetstyle, The Sartorialist, and other street style blogs. I know I am jealous of their looks almost everyday. Recently I’ve noticed some…

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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One of My Idols

{Images from Kelly Cutrone’s page on Facebook} I hope all of you know who Kelly Cutrone is. If not, you should. Ever since I first saw Kelly Cutrone on The Hills (yes I know I just said I saw her…


  • 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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  • Let’s do this Monday 👊🏼☕️
Shop my look via or the link in my bio ✨ 📸: @leighagardner

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Skater Skirts

{Images from my StyleSaint} Clockwise from top: Nasty Gal, Asos, Topshop, Urban Outfitters, Topshop Recently I’ve been loving skater skirts! For as long as I can remember tight  skirts have been popular, but they don’t flatter my body so  I’ve…

Happy Thanksgiving

{Images from my Tumblr} This Thanksgiving there is so much I am thankful for. Today I will be surrounded by my family and friends, all of which are healthy and happy. We will all sit down for a meal and…

A New York Story

{Images} For those of you that don’t know I have an obsession with New York. Though I’m not sure obsession is the right word because usually an obsession is bad or unhealthy, but this is completely healthy. From this post…


clockwise from top:Topshop dress, Madewell chambray top, Madewell plaid shirt, J.Brand jeans, J.Crew bracelet, J.Crew balls bracelet, Zara leather bag, Madewell flats, J.Crew jacket, Madewell sweater, J.Crew sweater I love shopping at places like Forever 21 and H&M just as…

Happy Weekend!

I’m extremely happy that it’s finally the weekend! Though I hope everyone has a better weekend planned then me since mine will be filled with work, studying, and college apps. So I’ll be drinking plenty of coffee hopefully looking just…

J.Crew Winter Collection

Clockwise from top:  J.Crew sweater, velvet shirt, bracelet, leather pants, scarf, blazer, jacket, flats, and sweater When I subscribed to J.Crew newsletters I never thought I would be getting emails every day about sales and special offers. Even worse (well…

What to Wear For the Holidays

1: Topshop2: Topshop3:J.Crew4: Nordstrom5: J.Crew6: Rebecca Minkoff7: Zara8: Topshop I love when the holidays begin. I’m completely against singing christmas music until December and I don’t think we should have Turkeys around until November, but once the holiday season begins…

Winter Boots

1: Coach2: Hunter3: Sperry Topsider4: Hunter5: Burberry6: Joule In the last week Boston has gone from being hit by Hurricane Sandy to a Nor’Easter. So the weather has been pretty crazy, and It has been hard to adjust to below…

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