Cupid's Pulse Article: What to Wear on a First DateCupid's Pulse Article: What to Wear on a First Date

By Maggie T.

First dates can be stressful enough without having to worry about what to wear and how to accessorize for the occasion.   By sticking with classic fashion that never goes out of style and wearing clothes that are comfortable, you can keep your anxiety level to a minimum.  Here are a few stylish yet comfortable clothing suggestions to fit three of the most common first date experiences:

Lunch Date

A lunch date is a bit more casual if it happens during the weekday, as you will both be dressed in business casual or work attire.   There’s not much you can do there.  However, if your lunch date takes place on the weekend, then you will have a few more options.  Whether it’s a picnic in the park, dining on an outdoor restaurant deck or at a local coffee house, lunch dates can be an invigorating way to start the day.

Cupid's Pulse Article: What to Wear on a First Date

1. printed scarf 2. cuffed shorts 3. woven top 4.sandals 5. mini messenger bag 6. aviator sunglasses

The key to this type of date is to keep it casual.  A light-colored, button down shirt and a pair of cuffed shorts looks clean and classic when paired with strappy sandals.  You can accessorize the look with a scarf to make it a bit trendy as well.  It comes in handy if you get chilly, and it’s an easy way to spice up an outfit. If the date is outside, a great pair of sunglasses is a must.  You’ll also need a go-to purse. This cross-the-body messenger bag isn’t too small, and it will keep your hands free.  Neutral and earth-toned jewelry and make-up will complete this polished-looking ensemble.

Casual Dinner Date

Are you going to dinner and a movie on your first date?  Movies typically aren’t a great first date experience because not much talking can be done while you are watching the screen in silence among hundreds of other film-goers.  However, if your date tops it off with dinner, then a movie can be a great icebreaker because it gives you something to discuss later on.   You may even get bonus points if you bring a large purse and fill it with your favorite candy to share.  If a movie isn’t on the agenda but a casual meal is, try not to pick a place that’s too loud; it can be hard to keep the flow of conversation going if you’re yelling back and forth.

Cupid's Pulse Article: What to Wear on a First Date


1. printed scarf 2. green handbag 3. black heels 4. green flats 5. skinny jeans 6. grey sweater

Skinny jeans and a cute top make are a great look for a dinner date.   You can dress this outfit up or down in a number of ways.   For example, you can pair it with heels for a sophisticated look or flats if you want to keep it casual. Either way, it works.  Similar to the above suggestion, bring along a scarf to tie the outfit together.  It’s always colder indoors, and scarves are much less bulky than jackets.   When you warm up, you can just stash the scarf in your purse.

Formal Date

The guy you’ve been admiring for weeks finally asks you out on a date.  He mentions a restaurant that you know is extremely formal.  What do you wear?   Whether it’s a fancy restaurant, a special event or the theater, there are only two words to describe this date: lucky you!  Don’t sweat because now is your time to shine and look fabulous.  Play up your best qualities and embrace your feminine side.   If you’re heading somewhere classy, you should absolutely wear a dress.  Don’t wear anything too short or too low-cut.  You don’t need to give away all the goods on the first date.    Play with fabrics and patterns, and create a look that leaves him imagining more and begging for a second date.

Cupid's Pulse Article: What to Wear on a First Date

1. sleeveless dress 2. evening scarf 3. teardrop earrings 4. dark nail polish  5. black strappy heels 6. heart pendant 7.  lace clutch


A pretty dress is an essential wardrobe piece in any woman’s closet — it can be dressed up or down, and it can be used for many different occasions.   This crème dress from H&M can be worn on a date, at work, or anywhere you need to look nice.  I’ve paired it with a black sequined scarf, but you could just as easily pair it with a black blazer or cardigan.   Keeping with the theme of dark accessories, break out a pair of black heels and a black lace clutch.  Don’t be afraid of dark nail polish either (it’s not goth!).  Dark colors work really well if the manicure is fresh.

Whether you choose to keep it casual on your first date or your special someone wants to make it fancy and special, it’s important that you feel comfortable with what you’re wearing.  The more relaxed you feel about your outfit, the more you can focus on the handsome suitor by your side.  Using these tips, your date will have no choice but to ask you out again.

Author Bio: During the day, Maggie works for, where she makes wearing reading glasses fashionable.  On her down time, she enjoys listening to music, trying new recipes, and traveling.