Now that the end of the year is a few short weeks away, we've already made tons of predictions about what will be trending in 2020, so we thought we'd take a moment to reflect on what defined our style in 2019. In the past year, our editors tried dozens of new brands, did a lot of shopping, and donated a fair amount from their closets, too. It's safe to say that as a group we tried hundreds of new fashion items since January began, so with all this collective shopping expertise under our belts, I was curious to find out what items went on to become our number one buys of the whole year.
As trend-minded editors, the below lineup naturally includes a few of the year's heavy hitters, but you'll also be delighted to find a few investment-type pieces that will remain in our closets even when 2019 becomes a distant memory. From the leather dress that earns Kat so many compliments to Anna's "boring" but very valuable trousers, keep reading for our favorite fashion buys of 2019 and see how we're styling them.
"This leather dress is by far my best buy of 2019. It's actually bizarre how many compliments this dress earns. I suppose part of why I love it so much is because I get constant positive reinforcement that it was a great pick from other people! The fit-and-flare dress shape is one I hadn't worn for a long time, but when reimagined in cool leather, it's such a good silhouette. It nips in at the waist and flares out over the hips, which, as it turns out, is a cut that makes me feel especially confident."
"I was actually a little hesitant to buy this bag earlier this year since it felt like it was everywhere, but it's been such a solid purchase (especially since it's still always sold out, but apparently the brown croc one is "coming soon"). It holds more than it appears and consistently makes everything I wear with it look a bit chicer."
"It's only been a month or so since I bought them, but I can already tell that these Proenza boots are my best purchase of the year. They're comfortable, easy to wear, and simple enough to go with everything but not boring thanks to the white contrast stitching. They're also patent, which means that even a little snow or rain won't stop me from wearing them in the coming months. Needless to say, I'm in love."
"I really love these J Brand jeans. For me, it's easy to keep relying on the same cropped blue jeans I wear all the time, but I think full-length, wide-leg jeans make me feel so much more put together and stylish without trying very hard. I've worn them with flat boots, heeled boots, and block-heel sandals, and they look good with all of these styles (and more). I wore them over thermal leggings in Copenhagen last winter, but during warmer months I wear them to the office with a band tee. Admittedly, I'm kind of self-conscious about my hips, so I usually pair high-waisted jeans with some kind of longline blazer or jacket. "
"I've been all about crossbody bags these days as a functional and chic way to accent my everyday looks. While I purchased a few different silhouettes over the year, it's my Louis Vuitton pochette bag that reigns supreme. I love its old-school yet modern feel. Believe it or not, the bag is actually not available as is. I wanted to try something nobody else would really have, so I purchased the classic pochette style (which comes with a small strap) and bought a statement-making logo strap separately to clasp onto it. It feels extra yet somewhat subtle at the same time. Given that Louis Vuitton monogram silhouettes basically never go out of style, I know I'll be using this bag for seasons to come."
"I'll admit that when I purchased these wool trousers, I didn't think that an item as 'boring' as trousers would become one of my best buys of the whole year, but boy did I underestimate the value they added to my closet. I'd been eyeing the suiting separates from the emerging Korean brand ever since I spotted my stylish friend Angela wearing them on her Instagram, so when I finally added the trousers to my own closet, I was happily surprised to find just how well they fit. They're the kind of staple item that always makes me look and feel put-together, which has me guessing I'll be wearing them for years to come."
"This is tough, but if I have to make just one selection, I need to come from a practicality/most-used standpoint, and hands down, my top fashion buy was these slightly flared jeans from Agolde. I wear Agolde almost exclusively denim-wise (I'm also obsessed with the brand's 90's Mid Rise Loose Fits and Pinch Waist Hi-Rise selections), but it was this pair (Vintage High Rise in Clamor) that won me over in 2019. I initially spied them on Managing Editor Kristen Nichols, and I immediately had to have them. As someone with super-long legs, it's often hard to find a bootcut or flare that aligns perfectly inseam-wise, but these feel like they were truly meant for my body. The rise is perfect, and I've found they look perfect anytime anywhere—be it out on Friday night paired with a skimpy top or a with a boxy-cut jacket or blazer at work. Oh, and they're also comfortable as heck, don't stretch or lose their crisp shape, and they bring in alllllll the compliments. I can't go a week without wearing them at least once."
"Knee-high boots are the sleeper shoe I never knew I needed and now I simply can't live without—whether I'm wearing them with trousers or ankle-grazing skirts."
"My favorite buy of the year is unquestionably my staple high-waisted straight-leg jeans by Citizens of Humanity. They are the perfect, flattering fit and have a cool vintage wash. I cannot tell you the number of times I've worn them in the past year—they're so easy to dress up or down, and I always get compliments whenever I wear them."
Next up, the eight jewelry trends our editors are over (and what they're wearing instead).
-
Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)Timeless with a capital T.
-
I've Lived in NYC, L.A., and Boston—Here's Everything I Think Is Chic for SummerShop the highly curated list.
-
Trust Me—Buy These 22 ThingsHere we go again.
-
All the Chicest Mother's Day Gift Ideas Every Mom Will CherishFrom pretty perfume to suede sneakers.
-
These 31 Anti-Trend Basics Are Quickly Becoming the Foundation of My 2025 WardrobeTake note.
-
10Best Knockoff Luxury Clothing Editors, 64 Spring Buys—Inside Our Seasonal Mood BoardsEverything inspiring our wardrobes this season.
-
You're Looking to Get a Head Start on Spring Dressing, and I Know Exactly What to Order—30 Chic Picks That Fit the BillA little something for every personal style.
-
39 Items All of My Chic NYC Fashion Friends Are Buying From ZaraAnd those are some picky New Yorkers.
