The Five Fashion Rules of Dating



It's Friday night, your makeup is on point, you're having a good hair day and you walk into your closet, and uh oh, what do you wear? It's your first date with that cute guy from Tinder and you want to look your best. You're questioning those red shoes. Do they give the wrong impression? You grab your boyfriend jeans, but are those going to make him want to be your boyfriend? Does that statement necklace give too much of a statement? Too many decisions, such little time! Having to pick the perfect outfit can be just as stressful as the first date itself. 

Don’t stress yourself out. Listen to these five fashion dos and don'ts for a first date... 

Heel With Caution 

I get it, you feel more confident wearing your highest heels, but remember to wear them with caution. The higher the heel, the later the date. So if you’re meeting for coffee during the day, maybe rethink those stilettos. You also want to take into account what you'll be doing on the date and how much walking is involved. You'll be regretting wearing those Jeffrey Campbell heels if you're going to be walking walking walking. Furthermore, don’t worry about whether or not to heel it based upon how tall your date is. If your date can’t handle you being taller than him, he ain’t the man for you. Heels are forever, but insecure men aren’t. 

Cover Up 

It’s important to always cover up, with a condom and a jacket. I know we’ve all seen one too many movies where the girl is jacket-less and cold and that’s when her date comes in to warm her up. But trust me when I say the cold shivering look is SO last season. There’s nothing sexy about goosebumps. What is sexy is a woman who remembers to bring a coat when it’s freezing outside. 

Less Is More 

Listen up ladies - I’m all for a woman who loves her body and loves showing it off. However, this doesn’t need to be done to the max on the first date. Sometimes, less is more. How you dress on the first date will set the tone for how your date views you. If all he sees is your DD breasts and your thong showing through your sheer dress, then basically that’s all he will see. A great rule to follow is to show off one thing at a time. Got a great rack? Fabulous! Show that off, but cover up those toned legs of yours. You want to lead with your best foot forward - not your sex foot forward. 

Confidence Is Key 

The number one thing most men and women find attractive is confidence. Therefore, when you are searching high and low throughput your closet, put on what makes your confidence shine bright. If you feel most sexy in that white dress of yours, but it’s a little last season, wear it. Your date will be too busy falling in love with you and your confidence, rather than noticing your dress is two years too old. So when you’re trying to decide between what makes you feel your best or what is most in style and on trend, go with the first choice. Confidence is key and hopefully that key will unlock a second date. 

Tone It Down 

You want to think of your first date outfit as one way you present yourself on a date. When you talk about yourself on the date, you usually don’t tell everything about yourself - you tone it down. You probably shouldn’t be sharing all of those crazy drunken college stories, or about how you have really bad B.O. after working out. Some things are better left unsaid during date number one. Think of your clothes in this light as well. Maybe you love to wear big, bright and bold accessories. That’s great, but think about toning it down a little bit. Instead of wearing crazy outlandish bracelets, rings and a necklace - stick to one statement piece and call it a night. You want to show off your style, without being a show-off. 


Sarah Altshule for

Sarah Altshule for

Sara Altschule is a blogger of all things love. She received her Master's in Psychology with the goal of helping people in the dating and love department. She is a relationship expert, lover of bagels, and considers watching TV one of her best hobbies.

For more relationship advice, dating tips or beauty how-to’s, check out Sara’s blog The Dating Department or follow her on Instagram @thedatingdepartment.