8 First Date Outfits Guaranteed to Help You Find Love

You stare down into a dark void⸺it’s almost cavernous. You could hear your own echo if you shouted loud enough.

You step into the darkness, your heart begins to race. Your lip quivers as chills begin to run down your spine like a flowing river.

You gingerly reach out into the darkness to try and feel your way around. Every sense is heightened, every sound, every smell, every feeling. The fear of the unknown clutches at your beating heart.

You’re not sure where you are or where you’re going but the feeling of unease twists and ties your stomach into knots.

The beat of your heart hastens to a virtual tap dance, your breath becomes shallower and shallower with every passing second as you desperately try to find your way around.

“Got it!” You scream in exhilaration. Finally, you find the light switch to your wardrobe.

But the feeling of accomplishment is suddenly washed away by an incoming tide of anxiety. You quickly realize you still need to pick an outfit for your first date “Ahhhhhhhhh!”

A first date can be pretty scary on its own but deciding what to wear on a first date is a total nightmare.

Don’t worry though, we’ll figure this out together. Allow me to be your shining light in that dark void we call the dating game.

What to Wear on a First Date to Dinner

Dinner dates can exist at either end of the spectrum⸺formal or casual. So take the venue into account when deciding what to wear on a first date to dinner.

If it’s a formal occasion, InStyle Magazine suggests a pair of chic black pants with a casual white T-shirt and low heels. But zhuzh it up with a statement necklace or your favorite pair of earrings.

white bodysuit

Black and white will never go out of style. Accessories will go along way with a look like this, however. Add something red for a bold pop of color.

A LBD and boots is a classic first date outfit too!

black midi dress

The Every Girl recommends a shift dress or skinny jeans and a silk cami underneath a blazer and heels for a dressy dinner date. A pair of boyfriend jeans with a cute blouse or tee is perfect for a more casual dinner. 

white blazer

I’ve said it before in my other posts but this goes double for a dinner date⸺don’t wear anything you don’t feel comfortable in. You should be able to eat and breathe in it!

What to Wear on a First Date to the Movies

A pleated maxi skirt is the perfect blend of date night formalness and loose, flowy comfort. Whether you’re sitting in the theater or a barstool afterwards.

pleated metallic skirt

If you can’t find the right top to go with your skirt, opt for a silhouette-hugging wrap dress instead. And stay cozy with a leather jacket.

One thing that tends to slip my mind a lot is despite the weather outside, movie theaters always seem to be a little chilly inside. So, if you’re going to wear a dress or skirt, just make sure to bring a jacket with you in case.

Not feeling skirts or dresses? A pair of wide-leg palazzo pants is the closest thing you can get to sitting on the sofa in your sweats.

A pair of jeans with a T-shirt and sweater is a failsafe option for the movies though. Bring a large bag like a tote so you can stash away your sweater once the movie’s over.

What to Wear on a First Date for Drinks After Work

If you’re stressing about what to wear on a first date to a bar after work, don’t worry. Odds are that they’re coming from work too. A blazer worn over a shirt and some jeans is fine.

You could plan ahead of time though and dress your look down by wearing a skirt with a feminine top, which you can hide under a blazer during work, and then just leave the blazer at work before your date. Ditching the structured work bag for a clutch is a good idea too.

black blazer

An all black ensemble is a great way to keep things simple but elegant. Add some personality with gold jewelry, belts and shoes for a pop of color. If done right, you can wear this look from the office to date night easily.

black jumpsuit

What to Wear on a First Date for Coffee

Coffee dates are all about keeping it casual, so dress comfortably. A pair of jeans with some Converse or flats and a t-shirt make for a perfect casual first date outfit.

The classic white shirt and jeans is a comfortable outfit you can easily style up or down as well.

white shirt and jeans

If it’s a little warm for jeans, an easy dress with an appropriate jacket, say denim or even a cardigan, is a great ensemble, too. You can wear flats or wedges⸺whatever makes you feel comfortable. 

Wearing a colorful skirt with a neutral top is a great way to have fun with your style and show off some personality. Bold colored skirts take confidence to pull off, which is just what you need to shake off those first date nerves.

yellow midi skirt

What to Wear on a First Date in Winter

Winter is not the time to be taking risks with your fashion, which admittedly leaves you a bit short for first date outfit ideas.

Depending on how cold it is, Style Caster says you have two options: either incorporate a jacket into your outfit, maybe jeans and a bomber jacket, or wear a big coat and wow your date with your outfit underneath. Kind of like the big reveal, ta da!

blazer dress

Using a long double breasted blazer as a dress is a great way to create a cool chic look. This is especially useful for chilly evenings. 

What to Wear on a First Date in Summer

A summer dress is the perfect first date outfit for the sunny season. Pair your favorite dress with some boots or sandals and voila!

summer dress

The type of dress you decide to wear can convey a lot of things to your date. So choose one that matches your personality and maybe even incorporate a fun print as a conversation starter.

zebra print dress

Alternatively, you could try a mini skirt with a floaty, long sleeve top for a cute first date outfit.

long knitted cardigan

A cami and cardi is a great layering option for slightly cooler evenings. If it gets too warm, just slip off your cardigan.

First dates are always going to be a little scary and that’s okay. But now that you know how to dress for them, you can feel just a bit more confident when the next one comes around.

A good outfit is one of the best things to help calm your first date jitters because if you feel comfortable and confident in what you’re wearing, it will show on your date.

Now get out there and start meeting people!

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