Of Everything I Bought This Year, These 8 Pieces Were the Best, Hands Down

I don't know about you, but I acquired a lot of stuff this year. I guess it comes with the territory when you're a fashion editor and basically shop for a living. Even though I always make an effort to shop wisely, I admit to making regrettable purchases from time to time. But I'm here to talk about the zero-regret ones that I've worn over and over this year.
Relatively speaking, narrowing this list down to seven items was a challenge, but those are the restraints I put on myself, so I adhered. I do love a good investment buy (especially when it's something I can wear on repeat, like a bag), but some of my best buys of the year were less than $100 and can be worn just as much.
Scroll to shop my smartest purchases of 2019. You'll find everything from the It bag I've been carrying constantly this winter to the Zara jacket I seriously can't believe I hesitated to buy.
Levi's Dad Jeans
I acquired a lot of jeans this year, but I have a special place in my heart for these Levi's. At 5'4", I need jeans that are the perfect not-too-cropped, not-to-long length that I can wear with a variety of shoe styles. These fit the bill, and despite being 100% cotton, they're ridiculously comfortable.
Loewe Lug-Sole Chelsea Boots
Not only are these functional, but they look even cooler on. I've always been bored by all-weather boots, but leave it to Loewe to turn something utilitarian into something beautiful. My favorite easy way to wear them is with wide-leg, high-waisted trousers or jeans and a cropped cardigan.
Shop a Similar Style for Less
Le Specs Fire Starter Sunglasses
I've worn my fair share of "weird" sunglasses, but this year, I wanted to go back to something a little more classic. These are still cool and youthful, but they have the added benefit of going with everything I wear, and they're quite flattering. (I find that a lot of sunglasses don't look great on me.)
Staud Olive Dress
Nanushka Trench Dress
Shop a Similar Style for Less
Wandler Georgia Bag
Shop a Similar Style for Less
Zara Crop Fleece Coat
Totême The Wide Shaft Boot
I had to have these beautiful boots from the moment I saw them. Unlike many tall boots, you can wear them over jeans and pants that are a little loose, thanks to the slouchy wide shaft. It's not surprising they sold out immediately, but Totême is regularly restocking them.
Shop a Similar Style for Less
Next up, the winter shoes wise celebrities wore in the '90s.

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
Shop 31 of This Week's Best New Arrivals
Buckle up.
-
I Went to Shop the Zara Sale But Got Distracted by These 27 New-In Buys and Never Looked Back
They are too good.
-
I'm Bored With My Closet—These 33 Chic Nordstrom Pieces Have the Power to Turn Things Around
Effortless and expensive looking is the vibe.
-
I Just Got Back From NYC, and Now, I Want to Order These 7 Trends From Reformation
My cart is very full.
-
Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)
Timeless with a capital T.
-
Let Me Cure Your Zara Fatigue One Chic Massimo Dutti Find at a Time
From summer-sale deals to brand-new arrivals.
-
A Rich-Looking Closet Is the Goal—31 Amazon Picks That Surprisingly Fit the Bill
Bring on the compliments.
-
There Are Over 500 Tops and Jeans at Zara, But Only These 32 Chic Picks Need Your Attention
I'll bet they'll sell out before July's over.