If I had to wear the same outfit every day for the rest of my life, it would be a variation of this one. Simple, classic and well suited for almost any occasion (if you swap out the heels for sneakers or simple flats; or trade the denim for cropped black pants).
I’m guessing you could recreate this outfit tomorrow for work or drinks easily. I know you’ve got a striped tee and well-worn denim and if you don’t have a classic trench – it’s time you invested. I picked up this one from Banana Republic almost two years ago and after a fresh dry cleaning, it looks brand new. It’s held up so well and not from a lack of wear. This time of year I turn to it on the regular. Gives simple work outfits an easy upgrade and can hide the flaws of practically any thrown together weekend look (basically the random crap I throw on running out of the house in a hurry).
Banana Republic Trench Coat | J.Crew Striped Tee
Banana Republic Boyfriend Jeans
Madewell Mira Heels (almost sold out, similar here)
My biggest tips when buying a trench coat is not to skimp and focus on fit. Find one you love, one that fits well (it needs to pass the Goldilocks test – not too big but not too tight) and wait for it to go on sale. I picked up this one when Banana was running a 40% off sale (which they are doing RIGHT NOW making this right at $100).