What To Wear On A First Date

August 18, 2021

Lace Cami I wit & whimsy

Nothing can kill the vibe of the excitement of a first date more than worrying about what you’re going to wear. That dreaded feeling of tearing apart your closet exclaiming “I have nothing to wear” – we’ve all been there. 

But I almost always follow a formula of a few date night outfit ideas so I can avoid that feeling of panic and instead focus on being hopeful about the prospect of the first date.

What To Wear On A  First Date

Of course on any first date we all want to feel and look our best. Which means it’s an opportunity to wear what makes you feel like a million bucks while also showing off your personal style. If you’re confident in what you’re wearing, you won’t be worried about anything other than the conversation between you and your date. Make comfort a priority and avoid wearing things that are cut too low or rise too high or poke or don’t fit right.  

When I do Q&As on Instagram I always get asked about first date outfit ideas so I figured it was high time I put together my guidance on what to wear on a first date to give you some ideas as you embark on or continue your journey within the dating landscape!

Dressed Up Blazers

Blazers are a great piece to wear on days you need to balance going from your office to a first date. But not all are great for first dates! Avoid any that are overly patterned or academic in vibe and instead go for ones that are more sleek with details like leather or if you want something more casual- look for a laid back fabric. 

Leather Jackets

For all Fall & Winter dates you can always rely on a leather jacket as the perfect topper.

Silk Camisoles

Silk camisoles are almost always what I reach for when it comes to first dates. They layer well, are comfortable and flattering and easy to rely on. Cami NYC makes my favorites.

Flirty Dresses

Going on a dressier first date or just love to be dressed up on first dates? Reach for a flirty dress. I like doing daytime florals for mid-day dates and reach for off the shoulder styles and little black dresses for evening dates.

High Waisted Jeans

I love wearing high waisted jeans on first dates so I’m not worrying about hiking up my jeans at any point. My favorite pairs make me feel great and go with a variety of tops.

Stilettos

Have a pair of stilettos or pumps you love and feel amazing in? Know the guy will be taller or don’t care about height differences? Don your favorite pair! Just so long as they are comfortable and won’t cause you any issues walking in them. Make sure they are broken in!

Fancier Flats

If you want to avoid any height issues, you can always reach for a fancier flat that you love wearing. A dressed up sandal or more timeless shoe like a ballet flat is always a good first date option in my opinion.

 

First Date Outfit Ideas

New Classics I wit & whimsy

Dressed Up Blazer with Open Toed Heels

My go-to date night uniform is a silk camisole tank with jeans, heels and depending on the season either an appropriate blazer or a leather jacket. It’s formulaic so it means I don’t have to worry about what I’m going to wear. 

Feather Blazer I Wit & whimsy

Blazer with Pumps

I love pairing a more fun, dressy blazer with a silk tank, jeans and pumps for a first date. I feel confident, comfortable and it’s a uniform that I don’t have to give hardly any thought to. It always translates well if I am heading to the date from a day of meetings.

Late Summer Style I wit & whimsy's Meghan Donovan

Silk Tank with Distressed Denim

I’ve always been a fan of dressed up distressed denim. I like the juxtaposition of adding a pretty, feminine silk with ripped jeans and a heel. Want to amp up the look even more? Try a low bun and dainty hoop earrings.

Reformation Cyprus Dress on the Beach

Black Summer Midi Dress with Espadrilles

My arms aren’t my favorite feature so I often love to wear dresses with a sleeve on a first date if the weather allows in the summer. A midi dress paired with espadrilles or a dressier sandal is the perfect date night dress option for me in the Spring and Summer.

J.Crew Liberty Cottage Dress

Floral Summer Dress

Perfect for summer dates, a floral dress works for daytime dates like brunch or a coffee date when paired with sandals or you could add your favorite summer heel for summer date cocktails.

Styling a Linen Button Down Shirt

Button Down with Denim Shorts and Sneakers

Doing something outdoorsy like riding bikes or going to a sporting event on your first date? This is a perfectly cool vibe for a casual first date.

Fall Dresses I wit & whimsy

Leather Jacket with Midi Dress and Heeled Booties

A great transitional weather outfit you can wear a more casual midi dress but dress it up with heeled booties and a cool leather jacket.

Styling Classics I wit & whimsy

Leather Jacket with Straight Jeans and Slingbacks

In the Fall and Winter I wear jeans on most of my dates. I pick a pair that make me feel good and are comfortable for dining in if I’m going on a dinner date. I like straight jeans in particular because they go well with a lower heel so if I’m not sure the height of the guy, I can go for a mid-level heel.

I love to pair my leather jacket with classics like a silk camisole or a button down.

Black Lace Dress in Paris

Little Black Dress with Dressier Flats

Most comfortable wearing flats on a first date? Reach for a dressier pair like a ballet flat and pair it with a little black dress.

Off the shoulder linen dress on Meghan Donovan of wit & whimsy

Off the Shoulder Dress with Dressier Sandals

This is the perfect silhouette for nighttime dates in the summer but could also work well for an afternoon coffee date.

Sarah Flint Natalie Bow Flat in Nude I wit & whimsy

Winter Classics- High Waisted Crop Jeans and a Sweater

An outfit like this translates perfectly from your desk to a first date for colder temperatures.

Meghan Donovan of wit & whimsy wears a Reformation dress perfect for date night

Little Black Dress with High Heels

Love to get dressed up on a first date? Or heading to a more swanky cocktail bar or soiree? Reach for a little black dress that makes you feel super confident. The little black dress is a timeless classic for a reason!

Meghan Donovan of wit & whimsy wears the Reformation Persimmon Dress

Summer Dress with a Denim Jacket

This is a go-to look for me for casual dinner first dates in the summer.

Everlane Slip Dress

Slip Dress

For summer weather, reach for a versatile slip dress. My favorites can be paired with sneakers for a more casual vibe or with heels for a slinkier look.

Sezane Gaspard Sweater I wit & whimsy

Date Night Sweater

This button down cardigan you can wear frontwards and backwards is a date night favorite for me all year round thanks to it being a lightweight knit.

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What do you love to wear on a first date? Like the styles you saw above? Shop Meghan’s Closet.

More First Date Items to Shop

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8 comments on “What To Wear On A First Date”

  1. Great post! I love all these outfits. What jeans are you wearing in the first picture with the black camisole and blazer?

  2. LOVE these easy and fun ideas! Do you happen to have a link to the black blazer with feathers??!!!!! I looked in “shop Meghan’s closet” and did not find it.

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