By: Author Gabrielle Arruda. You want your clothes and outfits on a first date to help communicate who you are, NOT give the wrong impression. A casual first date is any date that involves daytime activities or a very clearly casual evening setting.
A low-key bar or relaxed restaurant in early evening would also qualify. For a casual first date I advise to keep your shoes very walkable, your makeup simple, and jewelry streamlined. You want to look polished, but not high maintenance. Casual dates especially during the day can end up moving around the neighborhood, especially if they are going well. Things I love for a casual first date: Easy dresses, jeans with a chic top or blouse, dress with tennis shoes, non-jean shorts with a blouse, or a blazer with leather pants.
Things I would avoid on a casual first date: Body-con dresses, pencil skirts, super short anything, plunging necklines, outfits with lots of volume, and t-shirts without a layering piece over them. And, as an amazon associates member we earn on qualifying purchases. The silk camisole is flirty and fun, and the blazer can be taken off if you want to show a little more skin.
Worst date tips & dresses to avoid
The heeled boots are casual, but help you lengthen your body and proportions. Plus, they are easy to walk in as opposed to stilettos. Where to wear this outfit: This outfit is great for casual dinners especially when you have to go straight from workdrinks at a relaxed restaurant, a day at the museum, or any casual eating environment. Outfit Formula: Loose t-shirt, boxy blazer, leather pants, belt, beaded handbag, hoops, and heeled boots.
Why this outfit works: This outfit is effortless, flirty AND sophisticated. I would pair it with your hair down and a great lipstick for a chic first date look.
Where to wear this outfit: This outfit works best for evening activities. It will work for a dinner, drinks, and is flexible enough to work for most evening dates where the activities are unclear. I would not wear this for any outdoor dates or coffee dates, as the leather pants might feel over-the-top. Outfit Formula: Square neck knit dress with trench coat, heeled boots, statement earrings and shoulder bag for an evening outfit.
Same square neck dress with shacket, classic sneakers, gold link necklace and tote for a daytime date. Why this outfit works: Here you can really see the flexibility of foundational fashion pieces. This body con knit dress is sexy, but because of the knit material it is not overly revealing. The neutral color and length help it be versatile to be paired both for evening dates and daytime dates. Outfit formula: Sundress, strappy low heels, woven bag, hoops, and your choice of outerwear. Why this outfit works: This outfit is flirty and fun, yet still casual.
Where to wear this outfit: This outfit is great for outdoor dates, daytime city adventures, or even grabbing a coffee. It could work for an early dinner at an outdoor restaurant, but should be avoided How to dress for first date grabbing drinks, or more elevated restaurants. Why this outfit works: I love this outfit for a evening city date. It is chic, a bit sexy, and incredibly effortless.
The jeans make it casual, the bodysuit is flattering, and the leather blazer is an easy layering piece that you can keep on or off depending on the location or temperature. Bodysuits help keep your styling chic and clean. Where to wear this outfit: This outfit is great for drinks, dinner out, or even shooting pool or a dive bar. The leather jacket makes it casual and a bit edgy, but the overall look is still sophisticated enough to pass at a restaurant. Also the dark colors help if you are prone to spilling!
This outfit is also great for fancier daytime dates likes going to a museum or event together. Outfit formula: silk skirt, silk blouse, white classic tennis shoes, shoulder bag, and a gold link necklace.
What should i wear on a first date for every scenario
Why this outfit works: This outfit is flirty, yet simple. It gives off relaxed vibes but still appears feminine and put-together. I would pair this with my hair down or in a low pony. Where to wear this outfit: This outfit is perfect for coffee dates, lunches out, park dates, or even walking around the city. That being said, I would opt for full coverage underwear or a pair How to dress for first date booty shorts under the skirt if you think sitting in the park, or the activities of the date are in question. Better safe than sorry, flashing your date is never a recommended first move.
While you could pair it with heels, I feel like it is not as successful for a first date evening outfit regardless of the shoe choice. But ultimately, that will be your call. Outfit formula: Straight leg jeans, Silk Crop Top Tee, hoops, leather shoulder bag, and either neutral mule daytimeor red heel evening.
Why this outfit works: I love the simplicity of this outfit and the details really make this outfit a great first date choice. The silk crop top has trendy notes with the padded shoulders and tie detail yet it is still elevated because of the material. This outfit has two shoe choices depending on what time your date starts. For a daytime or casual date I would opt for the low heel, neutral mule.
It acts as a great supporting role for the look while giving you a little more height. For evening, I love the pop color stiletto that adds some oomph to your look and gives off flirty vibes. Where to wear this outfit: This outfit is fairly flexible. Depending on your shoe choice you can wear this to a daytime date or an evening date. For an evening date, I would wear your hair down. Outfit formula: Body con dress, white denim shirt, mules, pop color should bag, and hoops. Why this outfit works: This outfit is great when you want to be low-key sexy but not look like you tried too hard.
The dress is chic and the accessories are all elevated, but adding the oversized denim shirt adds the How to dress for first date we need and relaxes the outfit. This is great for when you are unsure of how fancy the location will be. The dress also shows off your body without showing skin, which is a great balance for a first date. Where to wear this outfit: I love this outfit for any daytime restaurant dates, or any semi-casual evening restaurant dates. The denim shirt can be removed if it feels too casual, and you are left with an elevated look.
And if you need a fancier layering piece you could add a blazer instead. Why this outfit works: I love the effortless vibes this outfit exudes. I also love a neutral print like this polka dot that adds interest without taking away too much focus. Where to wear this outfit: This outfit is great for coffee dates, walks around the city, or any outdoor park dates.
It would also work for casual dinners in outdoor cafes, but probably skews too casual for restaurant dinner dates.
First date outfit ideas
If you are worried about your jeans making your outfit too casual pay attention to the details of your look. Avoid jeans that have too many wear marks or holes in them. You could also opt for a darker wash like dark navy, black, or gray to elevate your outfit a bit.
And definitely focus on your supporting accessories; heels, jewelry, or a shoulder bag can add the sophistication you need. While this outfit has both a crop top and shorter skirt, the tights and boxy blazer make this a great first date outfit. Tights are a great option for colder weather first dates, without sacrificing style. The boxy blazer really balances out the heels and fitted dress in this first-date outfit idea.
This outfit really highlights my legs, and allows me to be flirty without showing too much skin. The high neckline on the dress also helps make it more sophisticated. A square toe heel is a great, trendy alternative to the traditional pointy heel stiletto.
If you feel like your jeans are veering too casual, you can try a neutral colored top with a unique texture or silhouette.
Picking a blouse you love or feel confident in will add some oomph to your casual jeans. If you love all-black, rock it. Also, adding tights to an outfit makes it perfect for those transitional seasons. Showing a hint of skin is a great way to keep your outfit from looking too frumpy.
An off-the-shoulder shirt is perfect for this as long as it stays up! The rest of her outfit is chic and flattering, but the peek of shoulder makes this a great first date look. Navigating the dating world is stressful enough! Do i have something in my teeth, are they checking their phone because they are bored, am I coming off well?
You have enough to focus on with a first date, so these outfits should help you get the date started on the right foot. Let your style bolster your confidence and make you feel like your best self, so you can focus on making witty conversation and not worry about an outfit that will fail you. This site embraces fashion and finding confidence, self-assuredness, and internal beauty through style. Find style tips, outfit inspiration, and fashion trend updates here.