Kaysha Weiner Photographer »

This post has been years in the making. Throughout that time I have noticed several tricks my couples have used when choosing their outfits. Clothing really does play a huge role in the overall look and style of a shoot, so by taking these tips into consideration you’ll be on the way to the perfect engagement photos.

In addition to the suggestions below, be sure to check out my ‘What to Wear’ Pinterest board for inspiration. I am constantly adding to this collection of images and its a great place to start. There are also great styling services like Stitch Fix, that will choose outfits for you based off your style and budget. This is super fun, and I have had several brides wear these items for the engagement sessions!

What to wear for your engagement shoot

Pick Two Outfits
To get the most variation out of your shoot, I recommend picking two outfits: a casual look and then something a little more dressy. This doesn’t have to mean heals and a dress if that’s not your style. But by choosing two distinct looks you’ll essentially have 2 engagement sessions in 1, score!

Complimentary Colors
When choosing colors, don’t be afraid of any particular shade or pattern. If it looks good on you and your skin tone, go for it! You do not need to match colors exactly between you and your fiancé, but as a general rule choosing complimentary colors looks best. Think beyond the blue jeans and white shirts, and more to date night outfits.

Follow the Pattern Rule
So you have a cute outfit, but your fiancé still needs something to wear. Choosing one outfit can be hard enough, but if you follow the pattern rule you’ll create a cohesive look between the two of you. The rule goes as follows: If your wearing a pattern, put him in mostly solids. If he is wearing a pattern, choose solids for yourself. Super simple, but this is a fool proof way to pair two outfits together.

Add Layers
Scarves, jackets, hats, you name it! Including these types of layers makes any combination feel a little more put together and adds that complete look.

No Logos
Stay away from choosing items with large or distracting logos across them. This can kill the look of your shoot because the viewers eyes will go directly to the logo, instead of you (where the attention should be).

Keep Your Location in Mind
Don’t forget to keep the overall look of your location in mind. If your planning on apple picking, riding boots with rich jewel tones is the perfect choice. Try to also keep the practically of your choices in mind. High heals may not be the best idea for a sandy beach, or rustic hiking trails. This doesn’t mean you can’t wear your heals, but be sure to bring flip flops or something you can quickly change into between shots. The most important thing is to feel comfortable in the clothes (and shoes) you picked, otherwise that will show in the photos.

Adding a pop of color with a chunky necklace, layered bracelets, or blinged out earrings can really be the finishing touch your ensemble needs. This is mostly a tip for the ladies, but guys can add to their look with belts, playful socks, and sharp looking shoes. Get creative, and this is your an opportunity to really show off your personal style.

Don’t Forget Hair & Makeup
Although not technically clothing related, don’t forget about hair and makeup for your engagement shoot. You will look at theses photos for YEARS, so splurging on some pampering to look and feel your best is always a good idea. Check out DryBar for the perfect hair, and Blushington for makeup. Both are great local resources if you don’t already have a beauty stylist.

Camera Ready
This may seem obvious, but make sure your final selections are pressed, hanging nicely and camera ready on the day of your shoot. Although I have many photo tricks, I cannot do anything to help stained or wrinkled clothing.

I will leave you with one last thought… rules are meant to be broken. So if you have an out of the box idea, or your not sure if something will work, email me over a few photos. I’m happy to help narrow down your selection, and give additional advice for your particular shoot!

My 2015 couples have been killing their engagement sessions! If this is any indication of the upcoming wedding season, I am in store for a beautiful New Year.

When Carley asked me if sequins photographed well, I got excited, like REALLY excited!! I love when my couples show off their style, and this look as beyond perfect for Carley’s bright a warm personality. I know I say this after every shoot, but I had such a great time with these two!! They come alive when they are together, and you can just feel their connection through the photos.

So excited for these love birds, and I cannot wait for their wedding next year with Pure Lavish Events!


As my 2014 wedding season comes to a close, I think it’s about time for another dose of behind the scenes photos! What happens behind the camera is often silly, strange, and just plain hilarious. While editing each wedding, I come across these photos taken by my second shooters, many which make me laugh out loud. I’m a big believer of not taking life too seriously, so in the spirit of laughing at yourself…


Epic bridesmaid photobomb, in 3,2, 1…


The facial expressions of Carrie and Kevin from Pure Lavish Events are priceless in this photo! My story telling abilities are clearly very dramatic!


Oh, you wanted me to TAKE pictures of the cake cutting? I’ll just help you cut it…


Baby Lemon has already been to so many weddings! Her mom rocking it at 7 month pregnant!


Love working with my two favorite NYC planners, Citron Events and Lydia Ross Events!


Trying not to get set on fire during the sparkler exit…


  • Carrie traver - Oh my word these are great!!! The one of you to right of the couple cutting the cake is priceless!!!!

  • Rachelle - Love these features! Your facial expressions crack me up! ;)

I love when my couples come to me with an idea for their engagement session. Julia and Ben wanted to incorporate a downtown coffee shop vibe into their shoot, and found THE CUTEST location to help bring their vision to life. In addition to some killer styling (great job guys), and being all around naturals in front of the camera, this cozy session was such a joy to photograph.

Looking through these pictures make me want to cuddle up with my favorite book and a cup of joe. So grab something hot to drink, sit back, and relax while I share just a few of my favorites from this lovely shoot. Special thanks to Dee with Swell Beauty for hair and makeup.


  • Brandi Welles - So much to love about this shoot! Adorable couple and amazing photos Kaysha!

  • John - Such a cute couple! Love the photo’s! Awesome jobs!

  • Rachelle - Such a cute location and couple! :)

My favorite part of this time of year is reconnecting with past clients for lifestyle sessions. It is always so fun to see how much little ones have changed, and watch families grow. You might remember this sweet family from their maternity session at the beginning of the year. This was my first time meeting their little girl in person and it was certainly worth the wait, because she is beyond adorable!

They took advantage of my yearly mini session special, and in 30 minutes we were able to capture so many sweet moments. If you are interested in being the first to know about my fall mini sessions and seasonal specials, you can sign up for my VIP list HERE to snag these once a year sessions.


  • rachelle - What a cute family! Love the natural setting and those big baby blues that Dad and baby share. So sweet!!