We’ll be the first to say it; first dates can be, well, absolutely nerve-wracking. From overthinking what you’re going to talk about to ransacking your closet for a date outfit idea that’s equal parts cool and spicy, a first date spawns first-rate stress.
When choosing your clothing, you’ll find all kinds of advice for the “proper” first-date look—but even on date night, we’re here to encourage you to unfollow the rules. Show up as no one but yourself.
So how do you put together pieces that make a second-date-worthy first impression but also say “Thanks, but no thanks” to style conventions? For inspiration, we’ve compiled five expressive first-date outfit ideas that’ll be your ultimate guide to carry you from drinks to dessert.
How Do You Choose a First Date Outfit?
Let’s kick this off with a little bit of first-date fashion philosophy. How do you know what to wear on a first date? What makes an outfit the one? Well, you definitely know when it isn’t a great option — you’ll want to take a rain check on an outfit with the wrong fit, style, or uncomfortable fabrics.
A good first-date outfit is one you feel comfortable and confident in. The one that looks and feels how you want to look and feel. It isn’t always the trendiest, nor the one you might think you’re “supposed” to wear. It’s the one that makes you feel like you.
Building a Unique First Date Outfit
Showing up as your authentic self makes all the first-date small talk that much easier. So before we get started on outfit building, here are a few general rules to make your next first date a walk in the park:
Try on outfits the day before to prevent that 20-minute pre-date rush.
Wear a few pieces you know you feel good in.
Try out that new
blazer coat or statement necklace to add a bit of boldness.
Remember that the goal is to show up as yourself.
Take a few deep breaths; you’ve got this.
Ready to unfollow some fashion rules? Let’s explore.
#1 “Wanna Go For a Coffee Sometime?”
Ah, the classic coffee date. Although your instincts might tell you that you need to blow your date away with a perfectly polished outfit—don’t overthink it. Coffee shops are meant to be a casual date, so pick out your most elevated basics and opt for a clean, comfy ensemble.
This look is quick and easy to achieve with a few tried-and-true pieces you probably already have. Try out the following look next time you’re grabbing lattes for your casual first date:
Start with a pair of drawstring pants. Not as casual as sweatpants, more comfortable than jeans—kick your outfit off strong with this athletic-inspired classic.
Slip into your favorite hoodie. To continue with the sporty, cozy vibe, pick out a monotone or graphic hoodie to match the pants.
Throw on a structured blazer. A blazer is a versatile, on-trend piece that somehow works with just about any outfit. Its structuredness seamlessly offsets the relaxedness of the rest of the outfit.
- Step into some sneakers. Amp up a neutral-toned outfit with your favorite pair of comfortable shoes, keep it classic with a pristine white sneaker, or choose comfort with those lace-up trainers.
Warm where you are? Don’t sweat it. Swap out the drawstring pants for drawstring shorts and the hoodie for a
#2 “Walk In The Park on Saturday?”
Romantic outdoor dates have come back into fashion. But achieving a balance between clothes you can sit on the ground in but aren’t overly casual can prove to be a challenge—one that we’re up for.
Enjoy getting to know your date without worrying about what you’re wearing with this two-part ensemble:
- Get dressed in a snap with a long, short, or no-sleeve coverall. As you romp around the park, this one-piece will provide the ease and style you need to comfortably enjoy the outdoors without tugging at your outfit. Check out our guide on how to style coveralls for more inspiration.
Select your most comfortable boots.
Sometimes, a walk in the park can unexpectedly turn into a marathon. Be prepared with a comfortable yet bold pair of boots.
Yeah, that’s it. For the cooler months, layer with a long sleeve or crewneck sweater to add warmth. An alternative to the coverall is the overall, which allows for a bit more room if you want to break out your favorite chunky knit sweater.
#3 “Have You Seen This Movie Yet?”
Despite sitting in the dark for a few hours, the cinema is the perfect place to showcase your personal sense of style and be comfortable. Opt for trousers which have a balance of stylish and comfortable.
Whether you have tickets to a heart-pumping thriller, corny romcom, or action-packed adventure film, start with these essentials:
Grab a printed button-up. Nothing says classic better than a well-fitted
button-up. Short or long sleeve; leave a few buttons undone if you want to push the casual vibe.
Have a sweater on hand. As movie theaters can quickly turn into refrigerators, make sure you’re prepared for a sudden drop in temperature with a pullover.
Pull on some trousers. Tie the color scheme of your look together with a reliable trouser that brings out one of the colors in your
- Step into a pair of loafers. You won’t have to worry about being on your feet much on this date, so opt for classic loafers.
#4 “There’s This New Restaurant in Town”
We’ve arrived at possibly the most intimidating of all—the dinner date. You’re sitting across from your date, wondering what to order, what to say, but imagine this. You walk in with a killer outfit that is both classic and effortless. Oh, and conversation starters? You’re overflowing with them.
Try this pared-back approach for an instant confidence boost:
- Turn heads during your dinner date with a button-up shirt. The silky smooth shine of a satin button-up is the perfect statement piece for a night out at the newest restaurant. We even have summer suit options for the perfect summer romance vibes.
Tuck your top into
slim crop trousers. The structured trousers offset the flowiness of the top and keep everything looking balanced.
Add some bling.
Whether you prefer gold or silver, slip on a few rings and a simple necklace for a touch of understated elegance.
- Step into a pair of low block-heels. Keep things comfortable with a low heel. If you’re feeling something a little more elevated, you can’t go wrong with classic oxfords or a Chelsea boot.
#5 “Let’s Grab a Drink After Work”
When you have to run to the bar straight from work, the last thing you want to do is an entire outfit overhaul in a cramped bathroom stall. But with just an extra piece on hand and a quick jewelry change, you have a whole new look.
To transition your workwear to a date-appropriate outfit, go for the following combination:
Go bold with
Who said pants can’t be a statement piece? Not us. Besides the dramatic cut of these pants, take it even further with a playful print or unique color.
Make it a set with a matching
Nothing will make you stand out more in a dimly lit bar than a powerful jacket that matches your trousers.
Throw on a
corset after work. At work, start with a button-up under your suit. Once you clock out, undo a few buttons and throw a corset over the top (pro tip: tie it in the back for a cleaner look, or twist it around to show off the lacing).
Don’t forget the jewelry.
If you started with minimal jewelry at work, swap it out for statement earrings, chunky chains, or layered rings.
Break Out of Gender Norms and Into Your Style With WILDFANG
No matter what you wear on your date, show up as who you are. We believe that style is fun, comfortable, and for you. Let yourself play around with new and old pieces, make mood boards, and mix different silhouettes to slowly craft your own personal style—not just what society tells you to wear.
At WILDFANG we firmly believe that norms are meant to be challenged. That’s why we offer clothing that supports every gender expression, from femme to masc and everything in between.
Whether you choose to lean into current trends with an oversized blazer or opt for a pared-down look with a button-down and trouser, our collection is here to fill in any closet gaps. Added bonus? We’re climate neutral certified so you can feel good about each purchase.
Vogue. These Are the Spring 2023 Trends Vogue Editors are Investing In Now. https://www.vogue.com/article/spring-2023-trends-editors-picks