Okay I have to admit, I have a love and hate relationship with plaid. I am not one who will throw on a flannel with jeans. It has never been me – well except maybe a brief time in college. I always felt self conscious in plaid and I think it is because I had a boyfriend tell me it made me look bigger. Fuuuuccck him! Right?!

Well, my ways are changing! The past two years plaid has become a fall and winter staple. A new type of non-flannel plaid has surfaced in the form of a jacket or blazer and I am all about this. I love how it pulls together an outfit and looks so effortless. Another positive about this trend is that it has rotated in and out of fashion since the 1990s. So, if you decide to buy into this trend on the high end of things, you know you will get your money’s worth over time.

I screen shot and save “Street Style” looks I like and came across these when I was looking at old photos. I am seriously in love with all of these. One of the jackets from my Favorite Picks section has just gone on the Holiday Wish List.

Street Style in NYC photo via Imaxtree


These picks are on the higher end of the price scale. I chose these as my favorites because they are pieces from brands I know will last a long time. Think of it as an investment. Plus, these three items are on major sale. 

My Official Favorite! — Rag & Bone Rona Wool Two-Button Blazer

Theory Power Bexley Plaid Wool Blazer Jacket

Joie Jemora B Blazer



More of this trend I love! Every budget was in mind when putting this list together as anyone can wear this trend – it’s a must have simple closet staple.