Style Guide

What to Wear on a First Date

Photo:  Kels Willis Tumblr
Photo: Kels Willis Tumblr

Going on a first date is always daunting. You have that anxious feeling of wonder. Will we have chemistry? Is he as cute as I remember? What am I going to wear?!

Whether it is someone you met in person or online what you wear on a first date is very important. When you walk through the door you are either solidifying or surpassing his initial opinion of you. Not too much pressure, right?

It is all about finding that perfect balance of looking you give a crap, without looking like you tried too hard. Have a Queen Bey moment so to speak.


So how do you look “flawless” without trying too hard? Do not stray from your personal style. It is very obvious when you do.

Ever see those girls who dress like the guys they date? He is a hipster and now she is decked out in Free People. Then, the next guy is preppy and all of sudden you cannot get the girl to put down the J. Crew catalog. Don’t be that girl.

The biggest mistake you can make is not being yourself on a first date. Show up dressed the way you think he wants you to dress and he will see through that veiled attempt quickly.

So, with all this pressure—what do you wear on a first date? Here are few outfit options to get the ideas flowing based on potential date locations!

First Date: Dive Bar

Photo: Fashion Diva Design
Photo: Fashion Diva Design

Sometimes the best first dates are the dates that are low-key. If your guy chooses a dive bar, be sure to wear something casual, but do not lose your femininity. It is okay to wear those boyfriend jeans, just make sure you are wearing girly accessories to balance things out.

 First Date: Swanky Lounge

Photo: Oh Va Darling Tumblr
Photo: Oh Va Darling Tumblr

If your guy chooses a high-end lounge that calls for slightly dressier attire, remember to balance to looking cute, but not like you are going to the club. That hot number you wore on Saturday night is great when you are out with your single friends, but sends a terrible message when you wear that on a first date. One word: easy.

Keep it classy fashionistas! Trying pairing a flowy blouse with an asymmetrical skirt. It is the perfect balance of sexy and cute.

First Date:  Outdoor Lunch

First Date Outdoor Lunch
Photo: Sincerely Jules

Lunch dates are a fun way to break the ice. This type of low-key date calls for a casual yet stylish outfit. Try pairing a crisp button down with white a pair of white distressed jeans. Be sure to throw on a cute pair of heels to shape your legs.

First Date: Nice Dinner

First Date Nice Dinner
Photo: The Divine Addiction

When you first date is ata restaurant that means the guy one has good taste (you go Glen Coco!) and two put a little extra thought into the date. What does that mean? It means, you have to as my friends and I like to say “bring it”. What is “bringing it”? It is making sure that every single detail down to your pedicure is perfect.

Try a monochrome look. Pair a black blouse with a white pleated skirt. Wear a bright necklace and clutch that give the outfit a pop of color.

First dates can be a little intimidating at times, but with the right outfit you will feel one step ahead. Remember, be yourself and what is meant to be will happen. Good luck out there single ladies!

xoxo Lex Loves Couture

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