Easy First Date Outfits to Look and Feel Your Best
Ease the Getting Ready Stress with These Foolproof Date Looks
Photo by cottonbro studio via Pexels
First dates are full of emotions. Excitement, possibility, and usually a little stress. Dozens of questions might be running through your mind as you get ready, like will it be awkward? Did I remember to wash my hair? Will we kiss? Will we fall in love and live happily ever after? Okay, maybe I’m getting ahead of myself. One other slightly more practical question you might have is, “what should I wear?”
Picking a first date outfit matters for a few reasons. First, you want to make a good first impression, and showing off your personality through your style is one way to do so. Secondly, you want to feel your most confident, and the right look can make a big difference. Selecting the wrong pieces might have you itching, shifting around, and feeling constricted. Selecting the right ones, whether it’s a cute mini skirt, your coziest sweater, or your superpower top, can bring out your best self. Looking and feeling like a million bucks can ease some nerves on a first date that so many of us feel.
But, choosing what to wear on a first date isn’t as simple as grabbing your favorite dress, and it’s helpful to have an idea of what to expect when going through your closet or perusing online boutiques. There’s a couple of key factors to consider when selecting your outfit.
(Photo by cottonbro studio via Pexels)
Tips for Creating Your First Date Outfit
Consider the Weather
The weather plays a huge factor in what we wear everyday, and that extends to date outfits. If you’re too hot or cold on the date, you’ll inevitably be uncomfortable. Keep an eye on the forecast ahead of the date, especially if there’s an outdoor component. If it’s a chillier fall evening, break out your best jacket. If it’s a hot summer day, a light dress or cotton top might be a good call.
Consider the Activity
Typically, you’d dress differently for going into the office versus going to a cocktail lounge with your girls. Dates should be viewed similarly. Depending on the activity, whether it’s a coffee date followed by a walk, nice dinner out, or nosebleed tickets to your local basketball game, each type of outing deserves a unique outfit that fits the theme of the outing.
Consider the Time
Like the activity, the time of the date impacts what you should be wearing. Daytime dates can be more casual affairs, and pieces like sundresses, light wash jeans, sneakers, t-shirts, and shorts are all generally considered appropriate. Nighttime dates usually veer towards more elevated style, like dark denim, structured jackets, cocktail dresses, and heeled shoes. With all of these tips in mind, let’s get into outfit ideas for first dates.
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Authors
Tara Larson is a freelance writer and editor with expertise in covering men’s and women’s style, streetwear, footwear, beauty, culture, and lifestyle. Outside of Rank & Style, her work can be found in publications like WWD, Stylecaster, Business Insi
Written By:
Tara Larson
Casual Dress + Ballet Flats
One of the most tried and true first date looks for a casual daytime outing is a casual dress. Think lighter colors and fabrics like cotton or linen for breathability, or jacquard for a more structured style. The beauty of a dress is it feels elevated and still free flowing and comfortable. Round out the outfit with a pair of ballet flats for a feminine touch that’s super easy to walk around in without sacrificing style (sensing a theme here). If it’s colder out, add a sweater and consider swap ballet flats for boots, or add tights for extra warmth.
Midi Skirt + Easy Top
Another comfortable and casual option for a day date is a midi skirt and a simple top. A skirt is a great option for feeling more dressed up while staying relaxed. For a more formal option, you can go for a silk skirt and a solid top, but if you want to go more dressed down, a tiered cotton skirt with a graphic tee is perfect, and as a bonus you can show off a little personality with your t-shirt. Shoe options are nearly unlimited with this combo. You can opt for anything from sneakers to sandals to combat boots.
Patterned Pants + Cozy Sweater
If skirts or dresses aren’t your vibe but you still want to bring a fresh look to a first date, consider patterned pants. Whether your style leans more colorful and whimsical, or classic and neutral, there’s a different design that fits in anyone’s wardrobe. From floral or gingham to polka dot or plaid, patterned pants of all kinds can be just the right choice for a walk around a museum or a coffee date outfit. Add a cardigan or sweater vest to the outfit for an understated but polished finishing touch. You can even mix patterns if you’re feeling extra bold.
Mini Skirt + Knee High Boots
First dates during the evening usually mean a slightly more formal activity, and therefore a more stylish date outfit. One of my go-to pieces for going out is a mini skirt. You can go for a timeless, not to mention versatile black skirt, or try out a unique print or texture. No matter which feels best to you, mini skirts pair well with just about any top. My favorite way to style a mini skirt is adding knee-high boots to it, and this look is especially great for a fall or winter first date outfit. When the temperature drops, just add tights.
Dark Wash Jeans + Heels
You really can’t go wrong with a fabulous pair of dark wash denim for date night. While trendy jeans are great for lots of different outings, a classic flared denim style that fits like a glove is the pair I’d go for while getting ready for drinks or a dinner date. Adding a sleek pair of pumps, kitten heels, or chic strappy sandals for warmer weather creates a timeless look that is universally flattering. Dark denim and heels are a great base to add any of your favorite tops to, like an off-the-shoulder style or a halter tank. Grab a cute clutch or shoulder bag, and you’re ready to go.
Sexy Midi Dress + Jacket
When in doubt, a dress for date night is the easiest option to fall back on. A midi style paired with a jacket is one hack to feeling confident without revealing too much. Choosing a longer hem length adds to the overall coverage, and a cute jacket is perfect addition for a breezy night. If you prefer a little more allure in your outfits, you can always pick a dress silhouette that has a tighter fit or has less coverage on top (think spaghetti straps, deep neckline, etc.) for a sexy boost. I don’t think you can go wrong with a silk dress and a leather jacket, but there are tons of options for both pieces to feel the most like you.
Cool Jeans + Easy Sneakers
An activity date implies a more casual outfit. But, you can still look great even if you’re not in a LBD. Jeans are a good option for a date at a game or bowling, since they can be comfortable and casual while still being structured. You can add extra fashion points with a pair like barrel jeans or cool cargos, or go for a classic bootcut silhouette. Cute and functional sneakers are perfect for an activity date, too. You can match your sneaker color to your home team, and you’ll automatically have socks on, which you’ll need for the bowling alley.
Cute Skort + Button Down
Even if you’re breaking a sweat, you can still look cute. Enter: the skort. The ideal combination of shorts and a skirt, a skort can give your outfit a dressy look without feeling too exposed and allowing for more movement, and it adds to the easiest summer date outfit. If you’re doing a more active date, like a golfing range or pickleball, an athletic skort or dress is perfect. Throw on a button-down top to elevate the look, and complete your outfit with your favorite jewelry pieces to dress up the ensemble and add more sparkle.
Matching Top + Bottoms
Take away the headache of figuring out a full date outfit by going with a matching set. Not only can you mix and match the pieces with the rest of your closet, but they’re an ideal option for dates. They can make you look and feel put-together with minimal brainpower. For a more heart-pumping date, you can select an activewear set, like cotton shorts and a coordinating tank. For activity dates that are on the more relaxed side, you can try out a printed maxi skirt and a matching vest top. Add comfy sneakers or strappy sandals to complete the look.
Authors
Tara Larson is a freelance writer and editor with expertise in covering men’s and women’s style, streetwear, footwear, beauty, culture, and lifestyle. Outside of Rank & Style, her work can be found in publications like WWD, Stylecaster, Business Insi
