Cheryl Shops

When it comes to skirts, I have a type: above the knee, tiered, with a slight A-line shape. Off the top of my head, I can think of five of these already in my closet, although I probably have more. There's a reason I have a type—it's the most flattering on my body—but the downside is that my wardrobe starts to look the same after awhile. This was the argument that ran through my mind as I was contemplating buying this skirt, but I decided screw it, I really love it—plus I had a Free People birthday discount to burn. Once the weather started to cooperate, I ended up wearing this skirt three days in a row, which I almost never do, but that's how much I'm into it. Long story short, just wear what you love.

Wearing a dress over jeans is one of those next-level styling tricks that you see on street-style blogs during fashion week—it looks amazing but seems way too complicated to actually pull off. I, however, was up for a challenge, and after some experimentation, think I landed an outfit that works. It's all about proportion and strategic unbuttoning so you don't look like a big old blob. Here's how I styled a maxi shirtdress over white skinny jeans.

I saved the best spring trend for last: shoes! More specifically, slingbacks, which I wouldn't normally qualify as a trend, but there are so many amazing ones out there right now, I had to feature them. The good news for my over-40 feet is that the best ones have low heels, many in that 1-1/2–2" sweet spot. The even better news is that there are slingbacks with all manner of fun colors and details. The best news? You can wear them right now.

When it comes to shopping, I don't always get things right the first time. It took me several tries to find the right gray jeans (more on that later), I'm still looking for a ribbed black midi skirt (I've bought and returned two so far), and I have yet to find the perfect white summer dress in spite of trying at least one new one every summer. This is probably the third or fourth linen blazer I've purchased, and it still might not be the best, but I think I'm getting pretty close. It's one of those pieces that I plan on living in for much of summer; I've styled it here with jeans and a tee—very classic—but think it will look just as good with a T-shirt dress and sneakers. It's the ultimate dress-up, dress-down, dress-however-you-want piece.

Spring is a time of year that sounds better in theory than in reality. After months of cold, clouds, and rain (or in most cases, snow), all I want to do is break out the bare legs and sandals. And yet some days are in the 60s and gorgeously sunny, and others are...kind of just like winter. When I lived in New York, I'd totally jump the gun and break out my summer clothes as soon as the thermometer hit 50 degrees, but now that I'm a Californian, I've learned to ease into spring. My wool coats have been put away for the season, but sweaters are still around; tights are back in my drawer, but I haven't busted out the sandals just yet. Spring transitional outfits are all about balance; here's how mine are coming together.

This next trend is a bit kooky, but it's fun, and I think it transcends style—you can wear feathers in an edgy way or a feminine way, or in many ways in between. It's also a bit easier to find on the higher end (Net-a-Porter has a wealth of feather-trimmed stuff), but there are lots of affordable options out there too. Here are my favorite feather-trimmed pieces for spring 2019.

When I was in high school, there was a certain segment of the population that wore tie-dye. They also wore cargo shorts, peace necklaces, and Birkenstocks; they listened to the Grateful Dead; and yes, the stereotypes were all true. So of course I avoided wearing it like the plague…until years later when I saw this Proenza Schouler tee at Barneys. I love layering it under a blazer—it's an elevated take on tie-dye—and I've had it for years. So when I saw that tie-dye is a big trend for spring 2019, I jumped at a chance to style it here. This is more of a weekend look—I went with a long cardigan instead of a blazer—but still hopefully a more polished, ageless way to wear it. In other words, leave the Birkenstocks at home.