I’ve had mixed results on first dates, but I attribute that to chemistry more than my attire (thank you very much). I’m a creature of habit when it comes to choosing what to wear for a first date. I’ve developed the practice of purposefully dressing “normal,” which for me usually means jeans with a lovely top and comfy shoes, after navigating dates with strangers for a few years. That description may give the impression that I don’t work hard, but that’s not the case. Being a very quiet person, I’ve come to the realization that I want my initial impression to accurately reflect who I am.
Nevertheless, I was interested in how other women dress for a first date because dating is a somewhat closed feedback loop process (it’s uncommon and, to be honest, strange to receive a review afterward). I therefore made the decision to inquire about my single friends’ date-night attire on social media. The next time it’s your turn, I hope crowdsourcing other people’s first date tips will make things lot simpler for you. Continue reading to find out more.
An “Interesting” Basic Top + Trousers + Layered Jewelry
My first concern when dressing on a first date is comfort. I know that if I’m happy with what I’m wearing, I won’t be distracted by the urge to change my attire throughout the date. My favorite outfit combo lately has been a basic blouse with a touch of trendiness (imagine an asymmetric or sweetheart neckline) and loose-fitting pants, which are my favorite wardrobe staple. I generally end it with a few interesting pieces of jewelry that can spark conversation.
Reformation
Cello One-Shoulder Knit Top
$78
I would purchase this type of shirt for a date night but also wear it for other occasions.
Lafayette 148 New York
Gates Flecked Donegal Tweed Pants
$319
A pair like this should be in every wardrobe.
Petit Moments
Layered Carabiner Pendant Necklace
$40
Flirty Top + Leather Pants + Platform Boots
“I want to be playful and flirtatious on a first date while showcasing my particular flair. In the winter, my go-to ensemble consists of platform Dr. Martens, leather trousers, and a lovely blouse that exposes just enough flesh. The secret to staying faithful to my style is accessorizing. To maintain a stylish and feminine appearance, I always wear bright red lipstick, a striking piece of jewelry, such as a gold necklace or bold earrings, and a little pocketbook. Finally, I prefer to finish the ensemble with a vibrant coat for a playful flash of color. — Emma Greis
Shopbop
Nili Lotan Carley Silk Blouse
$720
A good discovery.
MANGO
Wide Leg Leather-Effect Pants
$50
Trousers made of fake leather that merely appear pricey.
Statement Top + Flattering Jeans + Heels
“There is a science to my go-to first date attire, which is quite basic. You won’t look your best when you go out for the evening if you’re stressed out trying to put together an elegant dress. I often advise my friends to concentrate on picking shirts that accentuate their form without being overly exposing because their date will only see them from the waist up most of the time. I thus usually go for a statement top and jeans that fit me well, especially ones that lengthen my legs. Oh, and regardless of his height, he must wear high heels.” Sierra Mayhew
Jaded London
Checked Shirt Corset$84 $31
This shirt is the best when it comes to statement tops.
Good American
Good Standard Baggy Jeans
$82
These jeans have developed a cult following for a reason.
Jeffrey Campbell
Dress Code Sandal
$155
These adorable mules particularly appeal to WWW readers.
All-Black Staples
“I usually dress casually yet stylishly on first dates. I tend to wear all-black clothing because it makes me feel most at ease and secure. Leather never hurts in little doses”. Isabel Campbell
AllSaints
Dalby Leather Biker Jacket
$569
I adore this jacket’s boxy shape.
Nordstrom
Relaxed Fit Pima Cotton Crewneck T-Shirt
$40
a simple A+.
Reformation
Mason High Waist Wide Leg Pants
$178
The pants that everyone loves.
