How to select the perfect casual date outfit? Whether it’s day or night, here is the guide on what to wear on a first date, and be inspired by my own look!

casual date outfit shilpa-ahuja-chennai-indian-fashion-blogger-style-travel-look-outfit-casual

Hey gorgeous! First dates can be really fun and yet unnerving to prepare for. Especially if you’re excited about your date. You want it all to go well and you want it to end with the promise of a second date. And that’s what calls for a special outfit.

What to Wear on a First Date?

Just like an interview, at a first date, the conversation begins before you even open your mouth. Your style and body language send messages about you to your date, whether you like it or not. And that’s not a bad thing either, after all, you, too, are reading his subconscious signals. Your date may find out whether you made an effort, what kind of a person you are and even whether they want to take this any further just by seeing your outfit.

That’s a lot of pressure on a simple date outfit, isn’t it? But that’s why I’m here to help, just like any best friend should! ūüėČ So let’s start with the basics. Here’s how to select what to wear. Your casual date outfit needs to:

1. Be comfortable

A first date can go very far, if successful. You only have a shot at a real, meaningful relationship if you can spend quality time with them. If you really hit it off, you may want to have a longer date than you had first planned. So sometimes, coffee extends into an ice-cream, too. And you can’t send the subconscious message saying, “Look how comfy I feel with you,” in an itchy or over-tight dress. So if you’re wondering what to wear on a first date, choose a breathable fabric, the right fit and something that doesn’t make you fidgety.

2. Let you be yourself

Do you feel most like yourself in a pair of shorts, a skirt, a dress or jeans? Whatever it is, wear that. A little experimentation never hurts, but don’t try to be someone you’re not. If you’re true to yourself, your date will reciprocate and it’ll help him (or her) feel like they can be themselves in front of you, too. And that’s the foundation of a strong relationship.


3. Show that you made an effort

You wanna be comfy, feel like yourself and yet look like you put some thought into your first date outfit. So if you feel comfiest in drab clothes, a pair of pajamas and uncombed hair, that’s still not a good date night outfit. If you look presentable, it’ll show your date that you cared enough to plan your look, and it’ll make him feel special. It’ll also encourage him to dress up on the next date, make nice plans, and in the long run, these habits keep the romance alive!

4. Look effortless

Totally contradictory to my previous point and this is where it gets tricky! How can you show that you made an effort and yet look effortless? Well, the trick is to find the right balance. Your casual date outfit should look like you put some thought into it, but it should not seem like you overdressed for the occasion. You don’t want to seem like you got dressed for a gala when it’s just a coffee or dinner date. Seeming over-eager can also be off-putting and making the wrong impression on a first date is not a good idea.

Choose a comfortable yet cute date night dress and keep your venue in mind. For example, if it’s a casual dinner, a skirt and a mini-dress are classic outfits. For a coffee or movie date, jeans with a cute top or sexy jacket are simple outfits to try.¬†If you ask me what to wear on a first date, the answer doesn’t end with just clothing recommendations.¬†Keep your makeup light to go with the casual date outfit. And simple accessories go a long way.

What to Wear on a First Date shilpa-ahuja-indian-fashion-blogger-style-casual-date-outfit-look

5. Keep your body type in mind

Needless to say, whatever you wear should accentuate your best parts and hide problem areas. I’ve already written much in detail about this, so check out¬†How to Find Your Body Type and How to Dress for It. Dressing for your body shape will make you feel confident and will let you look your best, chicest self!

Casual Date Night Outfit Ideas

I don’t believe in fashion rules, so I really won’t mention that you have to wear a specific outfit. Or that there are certain “correct” answers to the question what to wear on a first date. It all depends on, as I mentioned before, what makes you feel confident. But here’s a casual date outfit I put together to inspire you. This look would be perfect for a summer evening of outdoor beer and pizza, or a first dinner date.

In this look, I’m wearing a romantic red rose appliqued skirt paired with a really comfy black top. I feel most comfortable in flared skirts as they give a lot of room for movement, unlike tight dresses, and they’re softer than jeans! So put me in a skirt anyday and I’m happy! Similarly, the top I chose is made out of simple stretchy teeshirt fabric and has a top sheer panel that looks sexy but not too overdressed.

Additionally, I chose black and red because I actually wore this look outdoors for travel, and it’s a dark color combination I can be in from day to night. Plus, pinks and reds give color to my skin and so they suit me well!


For accessorizing, I kept it super simple. Just added a black and red necklace and a classic pair of sunglasses. I kept the hair even more effortless, to balance the bright red skirt, which would look too party-ready paired with blow-dried hair! So I went with the wet hair look, just carelessly brushed to a side with my fingers, bringing out natural waves.

The makeup was tricky as that’s where I really needed to make the casual date outfit all put together. Ideally, for a date night, I’d choose a bright red lipstick, but for a casual first date, I’d tone it down to a lighter shade. So I achieved this look by lining my lips with a red lip liner over lip balm. And then I smudged it a little with my finger to blend and remove excess color. Finally I finished it off with clear pink lip gloss to give the light red dewy lip effect!

I paired it with some blush, a very slight winged eyeliner, mascara, filled in brows and neutral eyeshadow. I dusted bronzer over my jawline, under my cheekbones and on the sides of my nose to just add a little definition.


So, my gorgeous, I hope you liked my ideas on what to wear on a first date and how to choose the right casual date outfit. Hope you choose the perf dress for yourself that lets you be comfortable and feel like your best version! Show me your casual date outfit on Instagram by tagging me @shilpaahujadotcom and I’ll be sure to like your pic!

Kisses <3

I am wearing:
Top: Forever New
Skirt: Chicwish
Necklace: Zinnia, Cambridge MA
Sunglasses: Ralph Lauren
Makeup: Estee Lauder Invisible Fluid Makeup
Face Powder & Blush: Clinique
Bronzer: DiorSkin Nude Tan Matte Sun Powder
Mascara: Clinique High Impact Mascara
Eyeshadow: Sportsgirl Metallic Eye palette
Lip Gloss: Dior Addict 043
Red Lipliner: MAC Lip Pencil- Brick
Photo Credits: The Guy
Editing & Styling: Shilpa Ahuja

Shilpa Ahuja a designer and entrepreneur. She is the editor-in-chief of, which she founded with the goal of inspiring confidence in the modern working woman through fashion. Fashion has traditionally been for the rich, white, thin woman. That's how it evolved over centuries and that's how it's been represented in fashion media. But Shilpa believes that with the changing role of women in the society, fashion has changed, too. She believes that fashion is for everyone, regardless of their age, gender, color, body type and background. So she translates runway fashion into easy style advice that one can incorporate into their daily lives. Shilpa's work has been published in the University of Fashion blog and Jet Airways magazine. She is also an artist, illustrator and cartoonist. She is also the creator of Audrey O., a comic series that represents the lifestyle of millennial women. She enjoys creative writing and world travel. Her art has been exhibited at Harvard Graduate School of Design and the Aroma Hotel, Chandigarh and been published in Chandigarh Times. Originally from Chandigarh, Shilpa also has a professional degree in architecture and has worked in interior project management. She is also the author of the book "Designing a Chinese Cultural Center in India". Shilpa has a Masters in Design Studies degree from Harvard University. For feedback and questions, please email