How To Dress For A Date: An Easy Guide On What To Wear, Where

I am not interested in doing it until I find the right person. You see how I choose my shoes – they only go on my feet! – Cher Horowitz

Clueless might be a 23-year-old movie, but whatever Alicia Silverstone said back then is very true to today. While our parents preferred to meet face to face, we rarely want to say “hi” to our hot neighbor or strike up a conversation with a random stranger at a bar thanks to dating apps like Tinder and Bumble.

As much as it’s easy to cut down on time with awkward face-to-face encounters, I just realize that as millenials, we’re automatically programmed to swipe left and right to find our dream date. Are we becoming choosier than our favorite teen fashion icon?

Sure enough, we definitely are. (Duh! 💁) However, the main problem that’s been plaguing us more than boys (or girls, if you’re on the LGBTQ spectrum) is finding the right type of outfit to wear on a date. Given that we’re more dressed down than our parents (thanks, athleisure and streetwear!), I also realize that our penchant for casual gear is leading us into a sartorial mess that’s been blurring the lines of appropriate dressing. Based on wherever your date will be located, think twice before you pull up in your Lulu Lemons!

Here is my guide on wearing what to where:

  1. Fancy Restaurant

You and your date want to ball out like it’s Lady and the Tramp. Surrounded by upscale decor, sharply dressed suits and rows of wine bottles, is there anything from your closet that you can excuse yourself from wearing? In that case, you will NOT get a pass for wearing sweatsuits and leggings. Even if you’re on your period, I will still not give you the permission to wear loose and baggy garments. Also, the same rule extends to your sneakers.

If you plan a date that’s literally happening after work, please do NOT show up with a big bag. Not only does it murder your entire outfit, it gives the vibe that you’re not putting in any time to dress up. Ditto with cotton tote bags.

Instead of going for a plain ol’ cocktail dress, here are some options:

A) Lace dress with sandals, clutch and statement sandals


B) LBD with bling bling and pointy-toed shoes


C) Body-con maxi dress with a metallic cross body bag and PVC sandals

See the magic that a little dressing up can do? Trust me, it doesn’t hurt to look a tad extra.

2. Casual Restaurant/Bar

Less intimidating than a fancy restaurant, you can crunch in WAY more options! While the rule of big bags still applies, you can put away that teeny tiny little clutch as you’ll be seated around the counter. If you want to go hands-free, you can go for a cross-body purse. But if you want to wear a clutch, go for an envelope-sized one.

Since you’re at casual setting, dress smartly and take some risks:

A) Statement tee, miniskirt and metallic pumps


B) Jumpsuit, gold jewelry, straw bag and clogs


C) Off-the-shoulder dress with sneakers


D) Biker jacket, slip camisole top, high-waisted jeans, structured bag and sneakers

Feel the different vibes between all four outfit choices? Don’t feel scared to dress down while you’re still dolling up. If you are meeting up your Tinder/Bumble boo on a lunch date, these outfit options can work, too.

3. Park

If you and your boo wanna grab some burgers in the park, this is where you can wear your exercise clothes ath-your-leisure (see the pun there?). Since you don’t wanna expose too much skin on a first date, I’ve got you covered with these sexy, yet subtle outfits:

A) Bike shorts and a crop top


B) Sweatshirt and miniskirt

If you’re not up for dressing down, you can still amp up your fit with a flirty printed dress:

Tip: swap your leather bag for a straw purse as the latter doesn’t get damaged from sun exposure.

Since you’re gonna be sitting down in the heat, you might as well go for a shorter hemline and bring some sunglasses (or hat)! If you wanna wear sneakers, please DO NOT forget to wear socks as the heat plus, closed-toe shoes equals smelly feet.

Puh-leeze bring some sunscreen and perfume with you as the heat will make you sweat like a pig, smell like a dumpster truck and cook you up like a lobster!!

4. Concert/Art Gallery/Museum

Going to cultural places gives you the chance to (finally) express yourself. You have a pass to pull out the weirdest shit in your closet and make it look hot. Whether it’s an oversized shirt, statement pants or sparkly cowboy boots, let it go hard against the most basic things in your closet.

In case you are wondering what the hell to actually wear, here are some rad ideas below:

A) Printed oversized shirt with statement pants and black ankle boots

Option: You can go for a silk button-down shirt if you want to spice it up.


B) Black off-the-shoulder top, low rise printed pants and sneakers

(FYI: I actually layered TWO crop tops!)

Given that concerts can be held outdoors (READ: hot as hell!), here are some options to wear outside:

C) White on white

This is the perfect outfit to wear if you haven’t shaved your legs, TBH.


D) Kimono, camisole, shorts and boots

If you’re dying to stay in the shade, a kimono is the best way to keep cool as the sleeves protect your arms from burning outside.


E) Two-Piece Set

With so many advantages, you have the most freedom to experiment with any outfit. Let your freak flag fly, girl!

5. Sporting Event

I almost didn’t think about it, but figuring out what the heck to wear to a sporting event is seriously overlooked. No matter how many times we want to show support for a team you’re rooting for, nothing looks more cheesier than being spotted out in a jersey and coordinating team colors from head to toe. (Been there, done that!)

Whether it’s a football game or an F1 race, we can’t get any more excited than to dress for our adrenaline. However, not all sporting events have the same vibe and dress code.

If you wanna dress down at a football stadium, here are some options for you:

A) Parka, sports jersey, skinny jeans and knee-high boots


B) T-shirt, jeans, belt and sock boots

Tip: Just display the team colors through your makeup. In this case, I wore blue eyeshadow and red lipstick to flaunt my support for Paris Saint-Germain. (Seriously, I am THIRSTING over Edinson Cavani!)

If you’re at an elite sporting event, look no further than finding the appropriate vibe to rock your fit:

C) Racing jacket, miniskirt, cross-body bag and Chelsea boots

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Ooohhhhhh Pit crewwwwwwww

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Ideal for racing events like F1, incorporating some menswear-inspired elements like a racing jacket will amp up the sexiest staples in your closet. Although the dress code says smart casual, distressed denim and ripped tees are a no-no.


D) LWD with a logo-printed bag and mules


Perfectly fitting for a regatta or polo match, a thigh-grazing little white dress is all you need to cop the old school Marilyn aesthetic. Make it modern with logo-splattered accessories.

ICYMI, notice how none of those outfits have open toe shoes or white-colored shoes? Nobody wears them at ANY sporting event as drinks get spilled on the floor. It’s not worth it come home with beer-soaked sandals or wine-stained white sneaks.

Most importantly, you are there to show off your team spirit!

Apart from finding what to wear, here are some brief DOs and DON’Ts:

  • DO wear some jewelry. Nothing makes your outfit pop than piling on a bracelet or earrings.
  • DON’T expect your date to dress up nicely. It’s likely that he/she will show up in a t-shirt and shorts if you meet in a casual setting. (This has happened to me before as I’ve met guys dress up in gym gear ON a date! To all the boys out there, PLEASE DON’T DO THIS!!)
  • DO anticipate some weather changes if you’re planning to meet outdoors – this will give you the chance to plan your outfit better.
  • DON’T try too hard. Treat date dressing like you’re there to see for your BFF! After all, you are here to dress up for yourself.


What is your dream date outfit?

Published by

Michelle Varinata

Lapis - (n.) a layer Shrek once said that "onions have layers" as he was peeling one. Like an onion, I have layers. Born in Jakarta and raised in Singapore, I grew up being surrounded in a multicultural environment. Then, I moved to the States, where I lived in NYC and L.A. The creativity, hustle, bustle and vibe of those cities inspired me to become a blogger, journalist and influencer. Writing by day and living it up by night, I slay in the streets one OOTD at a time. Full-face makeup included, too. ;)

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