Your Date-Night Outfit Essential Is Right In Front Of You

Expectation: You show up for date-night and look like a total knockout (without putting in any effort, of course). Reality: You spent hours grooming pesky fly-aways, turning your bedroom floor into a mini war zone of discarded outfit options, and reapplying your cat-eye three times because you couldn't get the flick just right. And we're right there with you.

But sometimes less effort equals a cooler look (imagine that!), and your favorite wardrobe essential has something to do with it. We're talking about denim — the perfect foundation for a slew of ensembles that instantly read: Oh, this outfit? I just threw it on. You might overlook the staple because of its casual vibe, but with the right accoutrements, jean pieces can give your outfit the understated finish it needs. See how we worked the latest denim styles from Macy's into looks that work for every type of date, below, and soon enough the expectation vs. reality struggle will be a thing of the past.

The "Cultured & Adventurous" Date
Whether you're checking out an exhibit or getting schooled in a wine class, you'll want a chameleonic look that can go with the flow of the evening — you know, in case you two hit it off and a "have you eaten yet?" is thrown out there. Start with always-chic stripes paired with a tailored trouser in an eye-catching color. Sleek and shiny booties are easy to walk in and elevated, while a distressed denim jacket thrown over your shoulders gives the look a carefree, down-for-anything vibe.
The "Last-Minute & Low-Key" Date
If your on-again, off-again fling isn't a big planner, you're probably all too familiar with the zero-heads-up text. For an invite to something impromptu and laid-back, like hanging at your local dive bar or a casual Netflix and chill sesh, you'll want a look that's comfortable but with an edge. If you're coming from work, for instance, you can instantly take it down a notch by swapping your HR-approved bottoms for lived-in denim and cozy sneakers. Add a playful ode to the '90s with an embossed lunch-box-style bag.
The "Drinks & Dance Floor" Date
So you're in for an epic night of specialty drinks and tearing up the dance floor. It's a no-brainer that you need a look you can move in — and a stretchy dress is not the answer. Instead, throw on black skinny jeans that can easily be dressed up (and you don't have to worry about your hemline creeping up). Leave the painful heels at home in favor of sleek pointy-toe boots, and top it off with a sparkly halter top to keep the festive mood going from first impressions to last call.
The "Official Sit-Down Dinner" Date
While there's nothing groundbreaking about going out on a dinner date, our rapid outfit changes leading up to it would suggest otherwise. Instead of stressing about the perfect outfit combo, go for an all-in-one style, like a collared denim shirtdress. It has the same versatility as your go-to shift dress, but reads more cool girl, less cocktail party. Add playful pieces like a mint-green sweater, leopard booties, and quirky pins to show off your fashionable (and funny) personality.

More from Shopping

While most people count down the days until holidays, vacations, or birthdays, my calendar fills with red X’s until it’s finally fall. From leaves changing...
Who needs words these days with so many emoji keyboards to choose from — and to do the talking for us? On the heels of Kimoji, ChyMoji, and all the other -...
This post was originally published on April 22, 2016. Like mom jeans, it's a little funny when a stereotype sparks a fashion obsession. And while it took ...
Flex dancing, a dance form characterized by rhythmic waving, gliding, and contorting of the body, is often thought of as a man’s world. But there are a few...
From heading straight to the men’s section to memorizing the company’s delivery schedule, every dedicated shopper seems to have their own tips and tricks ...
This post was originally published on July 28th, 2016. The business-casual dress code is one of the most difficult to define, and that might have ...
This post was originally published in March 2016. You've done the research, talked to some friends about it, and decided it's time to quit fast fashion ...
(Paid Content) Classic white Keds have been in my shoe rotation since I was a wee one. As a picky shopper early on, this simple and economical option was ...
Sometimes, one glance at your Google calendar for the next day can leave your head spinning — how on earth will you get it all done? Maybe you've got a ...
This post was originally published on August 23, 2016. As great as summer dressing may be (the skimpy tank tops, breezy dresses, and super-short shorts ...
You never want something until you can't have it. So, each week in The Sell-Out, we're getting the scoop from your favorite retailers on what's selling ...
Some trends are easy to dive into head-first: Give us all the athleisure in the world, and we're definitely not complaining. Because no matter how many ...
We first heard about Nike's plans to really, truly make the self-lacing sneakers from Back to the Future Part II a reality back in March, after the ...
This story was originally published on October 8, 2015. You can expect to see a certain set of characters at every Halloween party. Cher Horowitz is in ...