I just got back from a relaxing and very sunshine-filled vacation to Florida and the Bahamas, and while New York weather isn’t quite cooperating, I still have poolside lounging on my mind. I’m waiting for the weather up here to catch up to what I just left, and while it’s a bit chilly and rainy outside as I write this, I’m closing my eyes and taking myself back to the tropics.

It’s late April, and that means one thing to those of us in our lates 20s and early 30s: wedding season is upon us. I already have a few save-the-dates under my belt, with invitations to arrive shortly, and as usual, I have no idea what I’m going to wear. Warm-weather weddings and my penchant to wear black year-round just don’t quite jibe, but there’s also no part of me that intends to buy a handful of pastel dresses just to make it to August.

I once heard on some HGTV design show that in order to successfully incorporate an accent color into a room, the color should appear in three places. I’ve never personally tested that theory, but it seems true. When working with the decreased surface area of an outfit, on the other hand, that number can be decreased to two; a single note of color can feel random or ill-conceived, but if you can pick up that color in a second, more subtle place in your ensemble, you’re on the way to success.

Sometimes, there’s virtue in not quite matching. Often, I look at people wearing multiple pieces that are obviously from the same collection and see someone that would do well to think a bit harder about how to assemble an outfit. (There are, of course, exceptions.) People who’ve found their stylistic sweet spot often look great because they successfully combine pieces that don’t intuitively belong together.

One of my absolutely favorite things is when a designer I already know and love starts designing handbags that I can get behind. It’s such an amazing feeling to see a great designer take on the accessory world and do well, and when it happens, I follow closely. The Rag & Bone aesthetic is right up my alley, with a downtown, cool-girl vibe for an everyday wearable line.

With New York Fashion Week coming up in just a few weeks, I’ve been thinking a lot lately about what we can expect to see on attendees at Lincoln Center. Even an untrained eye can spot the high-powered magazine editors in the milieu; there’s a level of refinement that they’ve mastered that few others possess. (Contacts at the best brands in the world don’t hinder that pursuit, obviously.) Other than a few over-the-top street style stars, editors mostly look luxurious and stylish, but also somewhat nondescript.

As some of you know, we have a sister site called TalkShoes that’s all about…well, you guys are smart. Designer bags and designer shoes go together like peanut butter and jelly (and maybe even better, because hey, fewer calories), so it only seemed right for us to head in that direction. Now that we’re in the shoe business, we thought we’d combine the two once a week for your pleasure in our new Perfect Pairs series.