New York City is arguably one of the most car-hostile metros in the world.
But even if I were so lucky to zip around the Big Apple in a personal automobile, the only luxurious part of the equation is comfort. Touch-and-go commuting to and from work is maddening and undoubtedly slower than taking the subway.
In short, the time it takes to get from point A to point B can’t be overlooked unless you think being “fashionably late” is actually a thing.
Forget about the post-work swap between my office armor for something I can proudly sport among the stylish nightlife. Nothing puts a damper on my Saturday than a last-minute dinner invite only to realize it’ll take an hour before I’m home to change out of my sweats.
So what did I do in the wake of this headache? I put together a series of dependable outfits that, outside of weddings and critical work affairs, I can rock virtually anywhere—and with a whole lot of confidence.
Between all of those getups, these are the pieces that I’ve found to be the most versatile. So even if mind-numbing subway journeys aren’t getting in the way of an otherwise quick change, consider the following garments that go from day to night like a Waffle House.
A Neutral Quarter Zip
A quarter zip is one of those garments that doesn’t overcomplicate things but still manages to add a bit of finesse to an outfit.
Unlike a crewneck or v-neck sweater, the zipper detail gives it a more tailored edge, and when paired with a button-up shirt underneath, it subtly highlights the collar area. It’s the kind of detail that makes a look feel intentional—like you actually gave it some thought instead of just grabbing the first pullover in your closet.
Another reason I swear by quarter zips? They’re the ultimate second layer when the weather can’t make up its mind.
Those warm days that roll into crisp evenings can be tricky to navigate, but a lightweight quarter zip bridges the gap perfectly.
You can toss it over a dress shirt and chinos for a workday that might end at a rooftop bar, or keep it handy for when your casual coffee date unexpectedly turns into a patio dinner.
One of my go-tos is the KPI Quarter Zip from Mizzen+Main. The fabric is ridiculously soft, and it strikes that perfect balance between fitted and relaxed. It’s versatile enough to wear with everything from jeans to tailored trousers, which is why I’ve found myself reaching for it time and time again.
This quarter zip is a no-brainer for day-to-night styling. The soft fabric and perfect fit—fitted but not too snug—make it versatile enough to pair with jeans or tailored trousers, so it’s basically always in rotation.
Minimalist White Sneakers
Minimalist white sneakers are like the Swiss Army knife of footwear—there’s almost no situation where they don’t work.
At first glance, they might seem too plain, but that’s exactly what makes them indispensable. Their clean, fuss-free design makes them the ultimate chameleon—equally at home with a pair of relaxed light-wash jeans on a lazy Saturday or dressed up with pleated slacks for an evening out.
For smart-casual daytime looks, I’ll pair them with slim dark-wash jeans and a neutral tee. When evening rolls around, the same sneakers can easily handle a more dressed-up vibe. Think dark chinos, an Oxford shirt, and a Harrington jacket.
What’s more, leather sneakers are practical. They’re easy to clean with a quick wipe, which is crucial when navigating city streets or the occasional spilled drink when I decide to play too hard.
I’d be lying if I said keeping them clean isn’t a bit of a commitment, but honestly, it’s worth it. There’s something satisfying about stepping out in sneakers that look as fresh as your outfit feels.
Plus, they age beautifully over time, gaining character without losing their charm. I still remember my first pair. They were slightly scuffed after a weekend trip, but somehow that only made me like them more. They became less of a pristine object and more of a story to tell—and it’s always story time.
Dark-Colored Chinos
Dark-colored chinos are quiet overachievers, which is exactly why you see every menswear brand trying to perfect them, let alone why they are making this list.
While everyone else is fussing over distressed jeans or stiff dress pants, my navy and olive chinos are in the corner, doing all the heavy lifting without breaking a sweat.
I have to specify that dark tones like black, grey, and navy should take priority over khaki or light colors. Darks are slimming, and in my experience, they’re also the only shades that can confidently transition between harsh office LEDs to mood lighting.
Style shouldn’t be the only consideration when it comes to day-to-night prowess, however.
For example, I’m a huge fan of the Upton Chino Pant from Mizzen+Main. The stretch makes them ideal for days when I’m zigzagging around the city. Meanwhile, the breathable fabric keeps moisture under control, another annoyance I find when wearing rigid chinos made from 100% cotton.
The stylish tailored design aside, the Upton Chino Pant is perfect for marathon days around the city. With its stretchy, breathable fabric, it keeps me comfortable and dry, unlike any other chino that isn't optimized for movement (or style).
What really seals the deal for chinos is their tailored yet relaxed vibe. They’ve mastered that sweet spot between “I care about my appearance” and “I swear this took five minutes.” It’s almost unfair how adaptable they are—like the wardrobe version of that friend who somehow charms your parents and your rowdy college buddies.
An Oxford Shirt
There’s a reason the Oxford shirt has earned its spot as a menswear essential—it just works.
Whether you’re layering it under a jacket for a layered look or rolling up the sleeves for something more laid-back, it’s a piece that doesn’t ask much but delivers every time.
Here’s why I go for an Oxford shirt before any other button up when I’m seeking something suitable for the entire day: rigid fabric.
It goes without saying that a collared shirt gets along with the appearance expectations of work and evening get togethers, especially with a crisp press. But even when I don’t have time to whip out the ironing board, a subtle crinkled texture with the sleeves rolled up exudes a carefree demeanor that only a drill sergeant would give you flack for.
A proper dress shirt, on the other hand, just looks plain sloppy if you didn’t give it a full pass with the iron.
I commonly wear mine with dark raw denim jeans and brown penny loafers for a put-together look without resorting to something elevated such as a sports coat. When night rolls around, the same shirt holds up with a couple shirts unbuttoned if I’m really feeling myself.
Another thing I appreciate is how durable and breathable a good Oxford shirt can be. You don’t have to worry about it wrinkling after a full day’s wear or losing its shape when you’ve been out and about.
A Harrington Jacket
Whether I knew before or after it went by a fancy name, I’ve always had a Harrington jacket in my lineup.
It isn’t a blazer or a bulky coat—it finds itself in the Goldilocks zone of simplicity and sophistication that doesn’t look out of place where I’m sporting it and with what.
It’s simple and streamlined, with just enough structure to elevate a look without making it feel overly formal. The standard Harrington jacket will either have a traditional fold-over collar or a biker collar, both of which add a refined edge to its otherwise neutral silhouette. For an added touch of detail and function, it’s easy to find a brand spicing them up with external pockets.
The cropped cut also adds a sharp edge. Whether you’re short or tall, the look flatters your frame without overwhelming it, while its timeless design ensures it won’t look dated next season—or next decade.
My favorite no-change-required outfit looks a little something like this: brown wool trousers, white sneakers, a button up, and my trusty plaid Harrington jacket. While the jacket itself is a statement, it looks perfectly at home alongside the tailored garments.
But what really makes the Harrington shine is its versatility across seasons—not just the time of day. It’s lightweight enough to wear on cool spring days but substantial enough to layer in the fall.
At this point, I’ve learned that life doesn’t always wait for a wardrobe change—and honestly, I’m fine with that.
After all, developing personal style is just as much about looking good as it is about dressing effectively in tandem.
Knowing how to spot do-it-all garments in a sea of menswear options, like a Harrington jacket or the right quarter-zip sweater, is totally worth going into the day with confidence—and no fear of looking lost.
