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…

Shop The Post

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

Follow Along

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…

SHOP THE GIFT GUIDE

Instagram

  • The rain wasn’t going to stop me from checking off the last spot on my Christmas bucket list - the new @ralphscoffee on the UES! ☕️🎄 Now begins the countdown to heading home 🏡 .
.
Shop my outfit with @liketoknow.it ✨ http://liketk.it/2yRCk #liketkit #whenwearholiday
  • T G I F ✨I’m so ready for a weekend full of christmasy things including Secret Santa with a few friends! 🎅🏼 What do you have planned this weekend?
  • Less than two weeks until Christmas 🎄 I have my list of go-to Christmas movies (The Holiday duh), but earlier this week @natalie_catalina inspired me to find some new ones with her holiday hit list! Are there any movies I have to watch this year? #whenwearholiday .
.
Shop this post with @liketoknow.it ✨ http://liketk.it/2yNso #liketkit
  • Christmas reds ❤️ Linked my favorite festive nail polish via the @liketoknow.it app ✨ Or shop directly via this link 👉🏼 http://liketk.it/2yMni #liketkit #whenwearholiday
  • Made it through Monday 👊🏼 Been feeling a little run down lately, but the countdown to a Christmas is definitely getting me through 🎄#whenwearholiday .
.
My festive striped scarf is under $20! Follow me in the @liketoknow.it app to shop! #liketkit http://liketk.it/2yKVA

Follow Me!

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…

Shop The Post

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…

Shop The Post

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…

Shop The Post

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…

Shop The Post

London Packing Guide + What I Wore

My 4 day trip to London was seriously a whirlwind – We arrived Thursday around noon and by Monday afternoon we were already back on the plane headed home. As with most trips I take I did excessive planning on…

Shop The Post

The Boots You Need For Fall

OTK Boots have reigned supreme for years now and they’ll always have a place in my heart (and my closet), but there’s a new boot trend on the horizon that I knew I needed to jump on this year. The…

Shop The Post

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.