We say this a lot, but that doesn’t make it less true or lose its meaning—first impressions are a big deal, especially on a first date. Yes, we are beating a dead horse (sorry to this horse!), but you want to get it right; there is no second chance to make a first impression.
That means balancing your particular personal style while matching the vibe of the venue of your first date. It’s kind of like you’re walking a runway, but you aren’t a supermodel, and you aren’t getting paid.
Too casual? Your date might think you didn’t put any thought into the meetup. And if you swing over into the too-formal territory, you are gonna look super out of place.
Let us help you find that middle ground with your first date outfit—we’ll even tailor it to where you’ll be spending your day or night!
Coffee Shop Cute
Coffee dates are always a laid-back affair. They’re the daytime rendezvous spots for people who love a good blend—not just in their cups but in conversation, too.
For these casual settings, opt for an outfit that says, “I’m here to get to know you better,” not, “I’m here to wow you with my ensemble.” This means a pair of comfy jeans (yes, they can have holes in them; this isn’t the opera) paired with a cute top or even a casual mini or midi dress.
You can elevate your look with some accessories—either delicate or statement jewelry, depending on your style. Shoes should be comfy but stylish—casual boots or your fav sneakers (not your going-out Chuck Taylor’s that have the bar sludge on them).
The same goes for the dudes: a pair of jeans and a casual shirt or sweater and boots or sneakers will do the trick!
Dive Bar Chic
Okay, you have full permission to wear your beat-up bar Chucks to a dive bar first date! These hole-in-the-wall joints are super relaxed, and you can have some fun with your outfit. This setting calls for an outfit that’s comfortable and a little edgy if you’re feeling it.
A fitted leather jacket over a graphic tee, paired with jeans and boots, is never, ever wrong. It’s effortlessly stylish and fits the dive bar’s casual vibe. You can play with textures and patterns if you’re in a bold mood—like a floral skirt with a patterned shirt—to show off your style without going crazy.
For the fellas, your first date dive bar outfit is the same as the one in the coffee shop.
Restaurant Elegance
Heading to a nice restaurant? This is your cue to dress up a bit. But “dressing up” doesn’t mean you have to pull out your most formal attire—no evening gowns are required.
For the ladies, a chic dress or a jumpsuit paired with heels makes a statement without trying too hard. Men can go for a tailored shirt with trousers and a pair of leather shoes.
You want to look polished, but not as though you’re about to walk down the aisle. Choose colors that complement your skin tone and add accessories that elevate the look—a watch, a belt, or a delicate necklace.
Winery Outing
A date at a winery? Oooh, country chic indeed! This outing means you can mix up casual and sophistication. You’re surrounded by scenic vineyards and sipping fine wines, so your outfit should be a little relaxed and a little refined.
For women, a maxi sundress paired with a light cardigan or shawl for cooler evenings is the perfect winery attire. Men could go with slacks, a button-down shirt, and a casual blazer to complete the look. Footwear should be comfortable enough for walking around, so think espadrilles or loafers.
Rooftop Romance
Rooftop bars or restaurants have fantastic views and are an excuse to dress up a bit. These venues lean towards chic and trendy, so choose an outfit that’s stylish and comfortable.
Women could go for a high-waisted skirt or pants and a fitted top or an LBD with a denim or leather jacket. Men should choose a smart-casual ensemble, like khakis or dark-washed jeans paired with a tailored shirt. Since rooftops can be windy, layering is your friend!
Concert Vibes
If your first date is happening at a concert or an outdoor music festival, your outfit should be as fun as the event itself. Comfort is the most important thing here, given you’ll probably be standing or dancing the whole time.
Women can rock a pair of denim shorts with a band tee or a lightweight boho dress. Men can sport jeans and a graphic tee—nothing fancy is required! Your shoes should be durable and comfortable, like ankle boots or closed-toe sneakers (there are Porta Potties at outdoor concerts and festivals, so protect your feet).
Add some accessories that add a bit of edge, like a stack of bangles or a wide-brimmed sun hat to go with your chic boho look!
Theatre Nights
Attending a play or an opera is an excellent excuse to dress up—way up. This setting calls for a more formal approach, but you don’t have to go full black tie unless the event specifies it.
Ladies can opt for an elegant dress or a midi or maxi skirt and top combo, complemented by a pair of fab heels. Men should consider a suit or dress pants with a velvet blazer—yes, we said velvet.
Accessories for both genders should be understated but classy—a pair of cufflinks or a delicate pair of earrings.
Amusement Park Fun
For a day full of rides and cotton candy, you should be comfortable, full stop. Does that mean you can’t be stylish? Not at all! Just wear an outfit that is breathable and isn’t constructed from thick or synthetic fabric.
Women can go for shorts and a cute tank top or a t-shirt dress paired with sneakers. Men can wear cargo shorts or jeans with a breathable polo or t-shirt. Since you’ll be outdoors, don’t forget a hat and sunglasses to protect yourself from the sun and wear SPF—you don’t want to end your first date early because you got sunburned!
Home Sweet Home
Although we don’t recommend this due to safety reasons, there are those who have a first date at home. This is usually dinner or a movie (Netflix and chill), which means casual but not too casual. They make elevated loungewear that is cozy but flattering. Just don’t show up in your PJs, and you’ll be alright.
Adventurers
For those adventurous souls planning a date that involves hiking, biking, or any outdoor activity, practicality is your fashion bestie. Breathable fabrics, comfortable footwear, and layers you can add or remove, like yoga pants, leggings, or shorts paired with a breathable tee and a lightweight jacket.
Sturdy sneakers or hiking boots will be required as well, depending on the activity. While you’re dressing to be active, you can still show off your style through colors and patterns! A bright top or a fun, patterned bandana can add a pop of color and personality to your adventure-ready ensemble.
Gallery Glam
Art gallery dates call for an outfit that’s as thoughtful and expressive as the art on the walls. You want something that stands out but doesn’t upstage the artwork. A smart-casual dress code works well here.
For women, a midi pencil skirt paired with a sleek blouse and comfortable heels or ballet flats can create a look that’s both sophisticated and creative. Men can do chinos with a crisp shirt and a blazer.
Beachside Casual
If your date involves walking along the shore or some activity on the beach, opt for light, airy fabrics that breathe and move. A maxi dress or a light linen shirt paired with shorts is both comfy and cute. Footwear should be beach-friendly—sandals or espadrilles work well.
Don’t forget the wind factor at the beach, so bring a hat or a hair tie. Round it out with your fav sunglasses and a tote bag for your beach essentials. For the men, throw on a pair of tailored shorts and a tee or a button-down with the sleeves rolled up.
Finishing Touches
No matter where your date is taking place, there are a few universal tips to remember. Comfort is the most important—you want to be able to focus on the person in front of you, not fussing with your outfit. But comfort does not mean sacrificing your style! It’s about finding pieces that make you feel good.
First dates can be scary, but deciding what to wear doesn’t have to be! By knowing the venue and going with outfits that blend comfort with personal style, you’ll not only make a great first impression but also feel more at ease. Just remember to wear your outfit; don’t let it wear you—your date is there to get to know you, not your clothes.
