This is a very common question. From my perspective, it's hard to say what you should wear overall. Your identity and image of yourself is one that should be captured during this shoot. Fun and silly, you should dress as such to a point. No, we don't want you in a clown outfit and makeup. Be yourself... be your best self. Often times the women are rushing to get to the engagement session because they run late at their hair and make-up appointment. Meanwhile, the guys are just chilling at home not knowing what to do and they just throw something on. Guys, this is a time to surprise your fiancé and make this something worth doing. While she is being pampered it's time for you to go get a manicure and or a hair cut. Look and feel your best. Have energy and a sense of exploration and passion towards the shoot. Here are some other key things to consider for you both.
Color coordinate: Just like your wedding day, your colors should coordinate in some way. Even if that is just a tie that matches her dress or a shirt that pulls the blue out in both your eyes. Have a purpose. Even though they may not be the same color of red, in the same family of colors will help pull you both together in the shots.
Sense of fashion: Women you read the magazines. You almost all do.... Okay, you all have at least. If you are a larger woman, you know that your arms are likely a spot you don't want to have that be a focal point, so don't wear sleeveless shirts or horizontal stripes. Even if you are fit as a cover model, know some limits. You will be walking a bit, so watch the heel heights or have shoes to walk in, and careful with the length of your dress or skirt as well. Photographers are always looking at different angles and it's very easy for us to upskirt you especially if your skirt ends at your cheeks. Jeans and a white T-shirt are for family photos and frankly are used too often. A jacket is an accessory but should not be your only option because it's hiding a shirt you wish you had not worn. The key here is to simply think it through. A suit is not always necessary guys, but if your woman is out dressing you, you will wish you at least met her half way... meet her all the way! This couple was simply awesome. Playful, fun and willing to give it their all. They knew exactly what they wanted.
Colors or patterns: Wear solid colors if possible. If you are more likely to wear a pattern make sure its more subtle and not a distraction. You want people to see you, not your purple fuchsia paisley skirt and a yellow shirt. Yes, I just made it up. Also consider your location. Although rules are meant to be broken, so they say, a suit and tie might not work in a grass field but honestly the contrast might just work. But going to shoot at the Disney Music Center with a pair of shorts is a big no-no.
How many outfits: This is really up to you, from our perspective. Many photographers limit the amount of "looks". For us, you can spend what ever time you want getting dressed and redressed but remember its 2 hours or so to shoot. At least do 2 looks. One dressy and one more casual, but please again appropriate to your setting. If you have a question, just send us a quick snapshot of what you were thinking of wearing and we will let you know.
It basically boils down to these DONT'S:
Don't wear all white head to toe. If you do, please have some color option for the next look. Guys, don't wear white. Have some color to your shirt.
Don't wear baseball or other sports jerseys unless its a theme for both of you and even then make sure it's not going to be your only look.
Don't wear short shorts, short skirts or anything else that will make you feel uncomfortable during the shoot. If you are constantly pulling down, it is too short.
Don't wear the exact same outfit. You would not do this on a normal day, this is not the day to look like twinsies.
Don't be someone else. Be you. Be comfortable not stiff and relax and have fun. Be playful with each other. Show us how much you are in love. A touch, a glance, a kiss.
Here are some examples of some couples that just made their shoot the best. You will see some rules broken here. In general, the key is to be as comfortable as you can in your own skin. Clothes should accentuate the shoot and not be a distraction for the eye or for your confidence.