Dating in Style: How to Dress for Every Kind of Date


We all understand the stress that comes with getting dressed for a first date. That’s why stylists from fashion rental service Armoire and matchmakers from dating service Three Day Rule teamed up to discuss this very topic. After having similar discussions with our members around balancing busy lifestyles, dating, and evolving personal style, we thought getting together to answer your burning questions would be a useful idea.

Your questions answered…

John and Jenn Faux

Suede Moto Jacket

valued at $245

1. I never know what to wear on a first date? What’s a safe and appropriate go-to look?

Number one rule  - wear something that makes YOU feel good. That could even be great jeans, a soft tee with a sleek leather jacket. For a date, punch up your look with a pair of heels and maybe a fun piece of jewelry.

You’ll want to stay away from anything that is too constricting or causes you to fidget or adjust. You want to spend your time getting to know the person across the table from you, not adjusting your top or dress.

Adelyn Rae

Red Dress

valued at $235

2. What is the best color to wear on a date?

Red is an obvious because we’ve been trained to view it as a sexier color, so go for it! It’s all about playing up your features. So if you have light eyes, wearing blue or green would really make them pop.

The BEST color to wear is the one that flatters YOU the most!

3. Are there any styles I should avoid on a first date?

Anything too tight, too low cut, too short . . . too anything! Keep it simple.

4. What rules can be thrown out?

I think almost anyone can make a stylish exception to all the canonical fashion "rules.” Just make sure what you wear is the right weight for the weather. There's nothing wrong with white in winter, by the way.

For every kind of date…

Dive Bar


Jeans, a button down shirt or t-shirt, and a moto jacket work great, especially with casual ankle boots.




Casual, but something still put together. A blouse with jeans and some fun flats always feels great.



Work to Cocktail Hour

Bring some big earrings, or perhaps a statement necklace, depending on how plain or decorated your top is. Take off your blazer, or throw it over your shoulders. Unbutton a button or two; and bring some fun heels to work too. Make sure they work with what you'll be wearing to work as well.


Don’t forget to tag @armoire.for.all to show us all of your date looks!  

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