The Easiest Hacks for Crafting True Day-to-Night Outfits

Sponsor Content Created With Old Navy


Transitional dressing is an art form few have mastered. Just when we think we've nailed our workweek and date-night uniforms, our calendars remind us that there are also those more complicated days that involve multiple obligations with varying dress codes and typically zero time in between for getting changed. (Truly, we're tired just thinking about it.)

So what's a girl to do? Well, according to outfit-planning pro Courtney Kerr, editor of Kerrently, putting together looks that transition seamlessly from day to night is actually not as difficult as it seems. And she was willing to prove it, taking us through an incredibly jam-packed day that involved morning coffee with a girlfriend, back-to-back business meetings that ran late (always!), and rushing straight to a dinner date, all without missing a sartorial beat.

Curious to see how Kerr took a single look through a busy day? All that's needed are a handful of styling tricks, a few key pieces you're guaranteed to already have in your closet, and one secret-weapon pant style from Old Navy.

casual coffee


Kerr's coffee-date look can be described in two words: effortlessly chic. She paired her must-have Old Navy Stevie pants with an untucked pajama-esque button-down and everyone's favorite pair of loafer slides. The aim, she told us, was to land squarely between "casually thrown on" and "perfectly styled." Case in point? Her slip on loafers and chic messy bun.


Her trick for getting out the door fast? "I keep a [separate] rolling rack of my newest purchases, pieces I rediscovered in the back of my closet, fresh items from the dry cleaner, and classic favorites. So I usually go to that rack first when it comes to outfit planning," she tells us. While we rarely store the results of any recent shopping spree too far out of reach, we'll be implementing Kerr's advice ASAP and keeping our favorite fall pieces front and center. Now we have no excuses for showing up late (okay, except traffic, weather, missing car keys…).

midday meetings


Before heading off to her meetings, Kerr tucked in her shirt and buttoned it to the collar, adding a tailored blazer, a structured bag, and low-heeled ankle boots. While the sleek accessories certainly don't hurt, our greatest takeaway is that restyling an oversize shirt instantly elevates a look. 


When styling a pants-and-blazer look, Kerr suggests keeping one piece fitted and the other oversize—that'll ensure that you look polished rather than frumpy. Since her Stevie pants are a slim fit, a more relaxed boyfriend jacket is the perfect match.

Dressy Date Night


Kerr credits the faux-suede material of her pants for her ability to dress up her daytime look for fancier evening plans with ease. She also notes that the material strikes the perfect balance between comfort and style—what more could you ask for from a transitional outfit?


Her top tip for tweaking her look for evening: "Tie up the silk blouse to really showcase the way the Stevie pants hug every curve," she says. We also love the way she replaced her blazer with an edgier leather jacket and swapped out her bag for a metallic mini bag. What really makes this ensemble work, according to Kerr? "When building an outfit for the day, I try to stay in a color-way that allows me to just switch out my shoes, add a jacket, or swap my tote for a clutch," she tells us.

Do you have a busy day coming up? Shop Old Navy's Stevie pants to get through stress-free and stylish. 

Associate Fashion Director, Branded Content

Michaela Bushkin is the associate fashion director on the branded content team. She is based in Los Angeles and is going on her sixth year at Who What Wear. Michaela has always worked in the content world, previously at Whalerock and The Zoe Report. Her current role involves executing content, photo shoots, and events for fashion brands from retailers to luxury designers and everything in between. She spends her free time online shopping (or "researching" as she likes to call it), reading at the beach, and trying as many new restaurants in L.A. as possible.