| On 2 years ago

9 Occasion-Appropriate Date Outfit Ideas for a Fabulous Night Out

Dress codes are so overrated, I know. Nowadays, you can pretty much get away wearing anything nearly anywhere—though it’s going to be near impossible getting into Marquee with those flip flops. Yes, Karen, I’m looking at you. But fret not, here are my two cents’ worth on fashion that’s appropriate for (almost) every occasion, and when’s a good time to pull out the bralettes, knee-high socks, and all that jazz.

1. Something Cute

For all the girls-next-door, I got you. Chances are your wardrobe is built on florals, bright colours, and dresses of all lengths. And I’m only able to tell you this because it takes one to know one. Let your date know that you’re fun, friendly, and feminine with this ensemble comprising of a mini dress and braids—an almost guaranteed way to charm your way into anyone’s heart.

Photo by Leo Goh / Sunflower Print Button Up Dress from Pomelo

Vibes you’re giving off: You’re generally happy, you enjoy spreading smiles to others, and you love those around you wholeheartedly.

Perfect for: Holding hands amongst the arresting aroma of elephant poop at the zoo.

Sunflower Print Button Up Dress from Pomelo | Buy Here

2. Something Classic

It’s hard to go wrong pairing a simple white top with denim—a timeless yet always on-trend get-up. Finish off with a classic pair of white sneakers, or switch it up with good old’ strappy heels. Who says safe has to be boring?

Photo by Leo Goh / Contrast Trim Crop Top from Pomelo

Vibes you’re giving off: You’re pensive, love reading, take your work seriously, and could never refuse a good film.

Perfect for: Cozying up while watching the latest blockbuster, with your date in one arm, and popcorn in the other. 

Contrast Trim Crop Top from Pomelo | Buy Here

3. Something That Shows A Bit Of Skin

If you’re the kind of girl that wants to draw attention to something other than your face, then this bralette and leather coat will surely do the trick. There’s no other way to put it—sultry and alluring is your brand, and tall, dark, and handsome is your man (well, hopefully). You’ll be sure to turn heads in an outfit that does nothing but justice to your figure.

Photo by Leo Goh / Outfit from Forever 21

And if you’re wondering whether the scarlet pieces I’ve chosen were purely a coincidence? I will leave you with the findings of a study done by Psychologist Owen Roberts—participants tended to rate the subjects more favourably in terms of attractiveness when they were wearing red-based clothing as compared to clothing of other colours.

Vibes you’re giving off: You’re fun-loving, you know how to appreciate a good party, and you’re here for a good time not a long time.

Perfect for: Meeting that one guy or girl you know you’ll never be ‘just friends’ with. 

High-Rise Velvet Biker Shorts from Forever 21 | Buy Here

4. A “You” Colour

When in doubt, always pick an outfit in a “you” colour—either a favourite colour or one you’ve often been complimented in. If you’re unsure, you can take a quiz to determine which colour best suits your skin tone here. And if your favourite colour isn’t in line with your skin tone-compatible colour, go with your gut. I will say one thing though—when dressed in a colour you like, this confidence will translate into your speech, thoughts, and actions, which is really all you need.

Photo by Leo Goh / Dress from The Editor’s Market

Vibes you’re giving off: You’re a no-frills kind of person, you love authenticity, and you have a good understanding of your wardrobe.

Perfect for: When you’re in full-blown panic mode half an hour after the time you were supposed to leave the house. Tsk tsk, Cecilia. Plan your time better next time, okay? 

5. Jeans, Sneakers & A Band Tee

Throw on an oversized band tee, a trusty pair of jeans, and your favourite worn-out Vans, and you’re good to go. A simple yet flattering outfit like this will show that you’re chill, casual, and that you don’t take life too seriously.

Photo by Leo Goh / Band Tee from LANY Store

Vibes you’re giving off: You embrace your inner band geek gal, you’re laid back, and you appreciate those around you for who they truly are.

Perfect for: Moshing on the vomit-laced floor of your favourite punk rock band.

LANY Dice T-Shirt | Buy Here

6. Something Classy

What better way to exude class than an outfit that gives off major Legally Blonde vibes? Decked in this Chanel-inspired tweed frock, it’s clear that you’re a woman of taste and it shows in all aspects of your life. Complete the outfit with a pair of mules or heels to give the whole get-up a certain je ne sais quoi.

Photo by Leo Goh / Mini Tweed Button Detailed Dress from Pomelo

Vibes you’re giving off: You’re mature, you know how to carry yourself in every situation, and you have exquisite taste.

Perfect for: Any date. Or sharing that one high tea set from TWG with Jenna whom you don’t even like that much. 

Mini Tweed Button Detailed Dress from Pomelo | Buy Here

7. LBD & Heels

Photo by Leo Goh / Crisscross Fit & Flare Dress from Forever 21

For the uninitiated, an LBD stands for none other than the iconic Little Black Dress that nearly every girl has, tucked away in the corner of her wardrobe. When all else fails, one can always count on the LBD for a look to suit almost any occasion. Slip on a blazer, and you’re interview-ready. Strap on a pair of heels, and you’re set for a full night of partying ahead.

Photo by Leo Goh / Janese Wrap Dress from The Editor’s Market

So whoever said that diamonds are a girl’s best friend clearly has not seen the inside of her closet—all hail the LBD, to whom we owe our chameleon-esque abilities.

Vibes you’re giving off: You love to look good, you’ll never be caught having a bad hair day, and you know what works in your favour.

Perfect for: Any date that you’re not paying for. 

Crisscross Fit & Flare Dress from Forever 21 | Buy Here
Janese Wrap Dress from The Editor’s Market | Buy Here

8. A Blazersuit

This piece might seem a tad too formal to some, but it’s a sure show-stopper if you’re going for a bold statement. It screams confidence and finesse—altogether an ensemble that shows you know what you want. I’ve picked this in seafoam for a more pared-down look, and the skirt finishing adds a touch of femininity to an otherwise masculine silhouette. Overall, choose this piece when you’re in the mood for honesty on your date, as studies have shown that people rate themselves to respond with higher accuracy when in formal attire.

Photo by Leo Goh / Mini Belted Blazer Dress from Pomelo

Vibes you’re giving off: You unapologetically command the room, you’re unafraid to pull off a power move, and most importantly, you don’t take bullshit.

Perfect for: When you foresee a tiresome night and a need to empty the contents of your glass onto your date if things go South. 

Mini Belted Blazer Dress from Pomelo | Buy Here

9. Something Quirky

Even though your sense of style might not necessarily conform to local fashion norms all the time, you’re unbothered and proud of it. After all, we do love a sis who owns her identity, and lets her personality show through her outfit.

Photo by Leo Goh / Darice Blazer from The Editor’s Market

This mishmash of purple tones and knee-high socks on me make an unlikely yet playful ensemble. Yes, it takes guts to show up in this for a first date, but it sends out a loud and clear message that you’re not for the faint of heart, honey.

Vibes you’re giving off: You’re loud, you possess a unique sense of style, you run on coffee, you love art, and you probably are a jack of all trades.

Perfect for: Galavanting around the museum—or park—depending on whether your date’s the indoorsy or outdoorsy type.

Darice Blazer from The Editor’s Market | Buy Here

But after all that’s been said, the last thing I’d want you to take away is that I’m policing your fashion choices. In fact, I’m doing anything but. Nonetheless, it’s always fun to dig into the depths of your wardrobe every once in a while, rediscovering that one tie-dye top you bought on impulse—almost like a game of treasure hunt, if you will.

Ultimately, I want to say this—no one else dictates your style except you, and as long as you’re comfortable and confident in your outfit, that’s what matters the most. Wear whatever you want, whenever you want. You do you, gurl.

Get the latest updates by following us on Twitter @hypeandstuff & Facebook Have an interesting story to share? Email us at
Leave a Comment

We're hiring lifestyle writers!