Last week, I talked about some general dating fashion tips, but this week, let’s get specific. How do you know what kind of date calls for what kind outfit? Check out the list below for some guidance:

Coffee date: Asking someone for coffee means “you’re a decent online conversationalist, and I’m ready to meet you in person, but I’m not willing to commit to anything involving time or money in case we don’t click in real life.” Due to the casual and brief nature of the coffee date, you’re allowed to look casual. However, because of the brief encounter, your first impression is even more important here. This means that you should take care to look good and presentable, even if you’re wearing casual clothes. Do not wear gym clothes, leggings, or anything that shows you clearly stopped by the date on the way from an activity that involves sweating.  A sundress, jeans, or a sweater dress and boots in the winter is perfect.

Drinks and/or dinner: I put drinks and dinner in the same category, because, if a drink date goes well, it will often lead to dinner.  Assuming this dinner date doesn’t involve a drive-thru window, look extra nice!  Ladies, this means a dress and heels (unless your date is shorter than you, in which case, use your discretion), or something equally dressy. Guys, slacks and a shirt always work – and tuck it in and use a belt!

An “activity” date: This can include bowling, hiking, rock climbing, or any extreme adventure from The Bachelor that doesn’t actually happen in real life.  You will be moving around, so you want to be comfortable (i.e., not pulling up your strapless bra or tugging at your dress), but this is NOT an excuse to wear some ratty old gym clothes.  ‘Athleisure’ is a thing for a reason.  Leggings (in good condition) plus a bright colored top and tennis shoes will do for the ladies.  Guys, clean clothes without holes and tennis shoes in good condition are acceptable. You might decide to go to a casual restaurant afterward, so make sure your outfit is versatile.

Wild card: In this scenario, all you know is that you’re getting picked up at 8. You aren’t sure where you are going or what you’ll be doing.  Unfortunately, you must be prepared for a multitude of situations.  You should be safe wearing something on a level between your coffee date and dinner date.  Wear semi-comfortable shoes in case you end up walking more than expected, and for either gender, you can’t go wrong with nice jeans and a cool jacket.

OK, you’ve nailed down a date. Nice work! Now, time to panic: what should you wear?  Selecting an outfit can be stressful – especially when you are meeting someone for the first time and want to make a good impression.  To start picking out a date look, ask yourself a few questions:

• What is my personal style? What types of things do I typically wear?  A first date is not necessarily the best time to try out a denim jumpsuit to see if you like it.
• Who is my date? A grad student?  A lawyer? A single dad? This doesn’t necessarily determine your date’s style, but it can provide a hint as to his level of formality.
• Where are we going? If you aren’t familiar with the place, do a little research.  Websites usually have photos and reviews where you can get a good idea of the vibe.

As much as we like to think that a date is only evaluating your personality, that’s just not realistic.   The truth is that your date is 78% more likely to ask you on a second date if he likes the way you look.  OK, I made up that statistic, but your appearance IS a very important factor in determining whether or not you will get another chance.  If you and your date are evaluating each other as potential soulmates, mutual attraction is one of the first things you’ll both notice.

A few general Dos and Don’ts about what to wear:

Do express your personal style but don’t dress in an extreme way.  Especially if you have never met before in person, you don’t want to embarrass your date by sporting something generally considered odd, like a tutu over jeans, or coat and scarf when it’s 90 degrees outside.  Also be weary of something super cool and trendy that may not be well understood by the opposite sex (harem pants, anyone?).

Do err on the side of being overdressed rather than underdressed.  You want your date to know that you value the time you are spending together and that put effort into getting ready!

Don’t wear anything too revealing. Yes, it’s a date, and yes, you want to look good, but don’t display all your goods. Keep things in proportion by highlighting one body part – so if you wear a short dress, pair it with long sleeves or a high neck, and sleeveless tops work well with longer and bottoms.

Guys – you aren’t off the hook here.  A first impression might even be MORE important for you, as girls (whether we like to admit it or not) tend to be more judgmental.  Although there aren’t as many rules for men, it’s important to look polished!  At a minimum, you should shower, shave, and comb your hair.  No one is impressed that you came straight from the gym.  Most date attire for men boils down to the skill of picking a combination of a shirt (polo/button down/sweater), pants (jeans or khakis), and shoes (no tennis shoes) that don’t horribly clash.  If you want bonus points, tuck in your shirt. Avoid cargo pants, and make sure your socks match your shoes.

Readers – what do you think?

PS – special thanks to JA, my sister/aspiring stylist for her help with this post!

Read Part II of this Post Here >>