3 Foolproof Date Outfits That Radiate Low-Key Cool

Sponsor Content Created With Amazon

Prior to a first date, there are many things to consider: Will they talk during the next episode of Game of Thrones? Will they think it’s weird if I speak directly to the dogs I meet on the street rather than their owners? And most importantly, will they judge me for ordering two dozen garlic knots in order to meet the delivery minimum of the pizza place across the street?

One thing that you should not have to stress about before a first date is what you’re going to wear. In fact, we’ve got you covered—with a little help from Amazon—in the form of three flawless looks that deserve a night out. Whether you swiped right on someone who likes to be spontaneous or you simply let your date-night plans creep up on you, these fall outfits are ready to go, cool girl–approved, and (best of all) they’re sure to arrive in no time. We promise: Even if the date’s a total disaster, your getup won’t be.

Need an instant outfit? Whatever your date night has in store, these three flawless looks (and Amazon) have you covered.


(Image credit: Clique Studios)

At first glance, that sounds like a great date-night suggestion. The only trouble is that between now and Thursday, you’re all but chained to your desk—it’s looking doubtful that laundry will get done, and your chances of picking up your dry cleaning are rapidly diminishing. Our solution: Opt for Prime delivery on these effortlessly chic tailored pieces. This single-button Rachel Zoe vest is the easiest thing to wear, and to us, it walks the fine line between cool and professional with ease.


(Image credit: Clique Studios)

This perfect blazer is one half of our new favorite pantsuit, which you can pair with dusty-pink sneakers and a logo tee to make a statement. Speaking of footwear, let’s just take a minute to appreciate these Marc Jacobs lace-up block heels and all the ’90s goodness they represent.


(Image credit: Clique Studios)


(Image credit: Clique Studios)

We’re of the belief that there are two types of people in this world: those who like surprises and those who don’t know how to dress for them. When your date suggests spending an open-ended afternoon together, you’ll want to find that sweet spot where your outfit is chic but daytime-friendly, and—if all goes well—can carry you through to nighttime.


(Image credit: Clique Studios)

When in doubt, start with great denim—we love these for the split-cuff detail and subtle ’70s vibe. (PS: If you have any interest in making your legs look super long, flares are the jeans for you.) This blue suede moto jacket is a little more approachable than your go-to leather version, and it adds to the subtle vintage vibe. Oh, and the midsize saddlebag? The strap is long enough to go hands-free by day, but it tucks in seamlessly to make your look evening-ready in a flash.


(Image credit: Clique Studios)


(Image credit: Clique Studios)

When you’re prepping for a night out, all sorts of wardrobe questions come up. How dressy is “dressy”? How would you define “smart casual”? And who are these people, anyway? Without being flanked by friends who tamper your usual style, it can be way more daunting to put together an “appropriate” look for an event you have no hope of getting a read on.


(Image credit: Clique Studios)

When any dress option just seems way too dicey, remember: Wide-leg black pants are the fashion world’s surest path to low-key elegance (and, more importantly, total comfort). Add a classic leather belt (it doesn’t get more classic than Calvin Klein) and a tucked-in, long-sleeve top that reflects whatever degree of formality you’re anticipating. For an outfit this slick and simple, we’re adding statement earrings and a pared-back beauty look.


(Image credit: Clique Studios)

Need a fresh look for a date ASAP? You can pick up all these outfits—and so much more—right now at Amazon.

Natalie Cantell
Executive Director, Brand Studio

Natalie leads the style direction for the all content we create in partnership with our friends at various brands plus the legendary team of editors who work on those shoots and stories. She loves collaborating and storytelling, so it's a really fun role for her. It's also the first full-time job she's ever had⁠! She started out in her career as a very mediocre model who agreed to her first styling job to impress a photographer she had a crush on, which led her down a happy path of contributing to Vogue Australia and working as a stylist, fashion writer, and creative director for all sorts of brands and titles. She has a bachelor of communications, but most of her career opportunities came up thanks to some fleeting and accidental street style moments. She's been at Who What Wear for three and a half years and still loves to work as a freelance consultant with brands and designers to shoot their campaigns in NYC. She's originally from New Zealand, and Bondi Beach is her second home, but like just about every other 20-something, she fell in love with New York at some point. She lives in Williamsburg with her fiancé and their weird little dog, Ruby. If you ever need reccies for feel-good fashion, legit coffee spots, politics podcasts, or non-intimidating yoga studios, she's very much your girl.