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16 Sep

What to Wear on a First Date

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he anticipation of a first date tends to conjure up a bad case of the "what ifs?" What if it's awkward? What if it's a waste of time? What if my nervous energy is obvious? And then, of course, things get even more severe when it comes time to pick an outfit. Is this too short? Too modest? Too showy? Too fashion-forward? The list goes on.


First-Date Outfit Ideas


As a single person who has been on countless first dates, I've gotten a lot better at challenging that internal dialogue because the truth of the matter is that there will be awkward dates and dates that you never want to see again. Yes, your date will likely notice if you are nervous, and some of them might judge your outfit. While this realization has also helped me see dating as a chance to have fun and connect with others—or at least walk away with a funny story and a lesson learned—one of my biggest takeaways has been of the sartorial variety.


Indeed, after much trial and error, I discovered that what I'm wearing has a lot to do with the success of a first date, but it's not the actual outfit that matters. To be clear, I don't measure success in leveling up to a second date (though that is a perk if we hit it off). Rather, it's about how I feel in my own skin, which means learning to dress for myself and only myself. After dozens and dozens of first dates, I've finally nailed the outfit formulas that meet at the intersection of personal style, mood, lifestyle, and occasion. 


So whether you're planning for a first date, 100th date, or even just a date with yourself, read on to see seven different first-date outfit ideas based on mood, occasion, and lifestyle, and play around with the ones that speak to you most. These seven formulas have never let me down. Hopefully, they make you feel like your best self, too. 


Date Outfit Idea #1: After-Work Special

what to wear on a first date to dinner


The Formula: Shirtdress + Fun Shoes


Why It Works: If you have a date planned during the workweek and you know you won't have time to change in between, opt for a classic shirtdress and then spice things up with a bright, edgy shoe. It's super comfortable and easy to style. Feels too stuffy? Undo a button. Feels too casual? Throw on a blazer. Sometimes I even wear this one on a weekend date if I want something easy yet put-together. 


Malina dress

Bardot Malina Dress $112 $56



Available in sizes S to XL.

Bare leather sandals

The Row Bare Leather Sandals $790


Available in sizes 35 to 42.

Date Outfit Idea #2: Classic Chameleon

First Date Outfits


The Formula: A Dressy Blouse + Relaxed Jeans + Midi Heels 

Why It Works: If you live in your jeans but want to dress them up a little, opt for a wrap top or something in a more formal material like silk or velvet. Then add a shoe with a low heel to strike the balance between comfort and elegance. I call this one the chameleon because it's elegant yet laid-back, and you won't have to worry about being under- or overdressed. It's my go-to look when I'm feeling unsure in any way. Plus, there are countless iterations since all you need to do to make it new again is swap out the blouse. 

The Curvy Perfect Vintage High-Rise Straight-Leg Jeans

Madewell The Curvy Perfect Vintage High-Rise Straight-Leg Jeans $115


Available in sizes 24 to 32.

Daniella Ankle Strap Sandal

Sam Edelman Daniella Ankle Strap Sandal $100


Available in sizes 5 to 12.

Date Outfit Idea #3: Oh, This Old Thing?

First Date Outfits Summer


The Formula: A Printed Skirt + T-Shirt + Flats

Why It Works: Just sassy enough to turn heads, this outfit formula hits the sweet spot between cavalier and thoughtful. It's perfect for anyone who fancies themselves a skirt person but also appreciates casual and comfortable clothing. I always go for a fun printed skirt (sometimes mini, sometimes midi depending on how modest I'm feeling) with a simple T-shirt half-tucked in, and then slip on some Mary Janes or ballet flats. Basically, just try to channel Alexa Chung. 

Short Sleeve Northside Tee

Madewell Short Sleeve Northside Tee $16


Available in sizes XXS to XL.

Leopard-Print Stretch-Silk Skirt

Ganni Leopard-Print Stretch-Silk Skirt $370 $111


Available in sizes 34 to 42.

Date Outfit Idea #4: Groove Town

First Date Outfit Ideas


The Formula: Going-Out Top + High-Waisted Denim + Low Heels

Why It Works: This is my personal favorite date outfit formula because it combines optimal, easy comfort with flirty, fun pieces. The hero here is the going-out top. Whether you opt for something flowy or form-fitting, off the shoulder or strapless, sequined, or ruffly, make sure you pick a going-out top that pumps you up and makes you want to have some fun. For me, that means my green silk bandana scarf with an attached rhinestone halter neck, but for you, it might mean an understated cami. It's basically like wearing a pump-up song, so ask yourself: Are you in a "Bodak Yellow" kind of mood or are you feeling a little more Lana Del Rey? Then channel that into your top selection. 

lace bodysuit

Cami NYC Bria Silk Satin-Trimmed Stretch-Lace and Stretch-Jersey Bodysuit $275


Available in sizes XXS to L.

slingback mid heels

Asos Samson Slingback Mid Heels in Black $40


Available in sizes 4 to 12.

Date Outfit Idea #5: Sporty Romance

What to wear on a first date for drinks


The Formula: Flowy Midi Dress + Sneakers

Why It Works: Super easy to throw on, a lightweight midi dress is the perfect thing to wear when you're out of ideas and craving comfort without compromising style. In fact, this outfit formula seems to garner the most compliments even though it takes the least amount of effort. Sometimes I opt for sneakers if I know I'll be walking a lot and want to be quick on my feet (and also helps to funk things up a little if I feel like the dress is too "sweet"), but other days and moods call for strappy sandals. Plus, it easily transitions from day to night. 

Réalisation The Amelia $210


Available in sizes XS to XL.

gucci sneakers

Gucci Ace Watersnake-Trimmed Embroidered Leather Sneakers $650


Available in sizes 34 to 43.

Date Outfit Idea #6: Endless Summer

what to wear on a casual first date


The Formula: Silk Cami + Jean Shorts or Skirt + Slides

Why It Works: If it's too warm for pants but you like the laid-back feel of denim, opt for a jean skirt or shorts depending on which ones speak more to your style. A silk cami will introduce a sleeker, sophisticated aesthetic and a pair of mules with a low heel will also dress things up. Breathable, light, and chic, it's a great summer outfit for pretty much any activity. 

Layla Washed-Silk Camisole

Equipment Layla Washed-Silk Camisole $100


Available in sizes XS to L.

levi's shorts

Levi's Rib Cage Cutoff Denim Shorts $80 $40


Available in sizes 26 to 32.

Date Outfit #7: Too Much Isn't Enough

Cute Date Outfits


The Formula: A Bold Blouse + Skirt + Sneakers

Why It Works: Opt for a fun, printed blouse and matching mini skirt with sneakers. I'm definitely not an understated dresser, and I used to think I had to tone myself down so as to not "come on too strong." Then I realized that if my date thinks my style is too over the top or distracting or weird—especially if they know I feel great in it—they are most definitely not for me. Moral of the story: Wear whatever you want to wear. 

Brown check mini skirt

Topshop Brown Check Mini Skirt $68 $38


Available in sizes 2 to 14.

Superga Core Classic Sneakers

Superga Core Classic Sneakers $65


Available in sizes 6 to 10.

SG Business

Joined on 02, Sep 2020  

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