Q&A: First Date Style

By Elina Furman

pic3Q. I’m in my early forties and live in a really conservative town. I need a great first date look that won’t make me seem like I’m trying too hard?  

A. Choosing an outfit for a first date can be brutal. Your first impression is vital to your success and should set the tone for the entire date. If you dress up too much, it will look like this is the first date you’ve been on in ages. Of course, if you’re too casual, it will seem like you didn’t care enough to put yourself together. While there are some rules of thumb that are universal, where you live can affect your choice of attire. For instance, while wearing jeans with an evening top might fly in New York City, the same look won’t work in a smaller, more conservative town. Of course, what you choose to do on your first date can change your look significantly, which is why we’ve broken down first date outfits by possible activities: 


Dinner and a Movie: For this standard first date you can’t go wrong with a simple wrap dress that emphasizes your curves. Flattering on every shape, you can choose a bold color or go with a simple black number depending on where you live. For accessories, a beautiful necklace will draw attention to your neck without looking too busy. 

Sporting Event: Unless you’re a sports fanatic, this first date pick may not be your top choice. Still, you can dress appropriately for the occasion without looking like his best friend. For a casual day look that will have him rooting for you, a nice pair of pants with a romantic, flirty top will do nicely. But if you want to amp up your feminine side, a casual sun dress will remind him that you’re all woman. 

Day at the Museum: Sophisticated gals who want to make a good impression without being too sexy would do well to make themselves look as cultured and put together as the setting. A pencil skirt with a crisp white button-down shirt is the perfect foundation for a day at the museum or art exhibit. To dress up the look, add some peep-toe pumps and some dazzling earrings. This look will work in any city and will make sure his eyes stay on you.


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