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Meet Chelsea. Corporate-America dropout, lover of all things old and firm believer in loving without counting the cost. 

MEET Chelsea

Deciding what to wear to your engagement session can feel a little daunting. You only have one chance, and you want to be sure you and your man are looking your best. That’s why I’ve put together my top tips for dressing yourself and your fiance for your engagement session. They’ll take the guesswork out of the decisions and have you both loving how your engagement photos come out.

As a general rule I love the way my couples look when they are dressed up! Casual looks are great, but I think this occasion calls for a classic yet elevated look. I always recommend my guys wear a suit or at least a button up & tie, and the girls wears dresses. They photograph beautifully, add movement and flatter your figure like nothing else. Choose an outfit you feel comfortable in, but don’t be afraid to dress up!


When picking your outfits together, I recommend trying to choose colors that complement each other rather than match. As much as we cherish those old family photos with everyone in white shirts and jeans, they don’t necessarily exude the editorial yet natural look you’re after for your engagement session.

So, if the groom-to-be is wearing a light blue shirt, the bride-to-be may want to choose a long, soft pink dress. To achieve a cohesive look between the two of you, choose a color-family, such as pastels or jewel tones, and pick your outfits to fit into the family you choose.

Softer, pastel colors tend to photograph best because they will not cast a color onto your skin. You’ll want to avoid bright pinks, reds or greens in particular as they are especially refelective. While I love bright colored clothing, take my word for it, you’ll look your best in those soft, pinks, blues, or beiges.

Another thing to keep in mind is the background you’ll be in. If you’re going to be in a green space, you may want to avoid green as you will not stand out of the photos.


One thing to be careful of when choosing what to wear to your engagement session is small, busy patterns. Often a small pattern will make a photograph look a little too busy and distract from you – the subject! Larger patterns, however, like floral dresses or tops, photograph just great. If you’re unsure about a particular pattern, try taking a photo of yourself in the mirror with the garment on. Is it distracting? You’ll be able to tell right off the bat.


One thing is for sure, heels make your legs look amazing. While heels may not be the most comfortable, I can assure you, it’s worth a little discomfort for the way the final images will turn out. If your heels aren’t comfortable for walking, bring an extra pair of shoes to slip into in between shots.

If you’re unable to wear heels, that’s ok, too! Your photographs will still look incredible. I recommend choosing flattering, neutral sandals or flats. A pointed-toe flat will elongate your leg a bit, and can be a great alternative to a heel.


When it comes to accessories, less is more. I recommend choosing one statement piece — a large necklace, a hat, a scarf, a flower crown — you name it. These things will add a beautiful, editorial touch to your photographs. But be careful not to overpower your outfit with too many accessories. The goal when it comes to dressing is to showcase your beauty without distracting from it! Textures like lace and tulle look amazing in photographs, as well.

Dresses with sleeves are a great way to help slim your arms, if that’s a place of insecurity for you (we all have one of those!).

Number of outfits

Generally my couples pick two outfits to wear for their engagement session: a formal outfit and a casual outfit. I recommend saving your favorite outfit for later in the session, when you’re likely to feel more comfortable in front of the camera. Choosing more than two outfits will leave less time for shooting and we want to capitalize on that soft, golden hour light as much as we can!

Where to Shop: Ladies

First off, take a good look in your closet before shopping for something new to wear to your engagement session. If you’re anything like me, you have a closet full of clothes that you hardly wear. Save some money and the planet by using what you already have!

If you’ve come up empty with the closet search, here are some of my favorite shops for engagement session looks. I bought my engagement session dress from LuLu’s and loved how it looked!

Rent the Runway
Morning Lavender
J. Crew
Free People

For the Guys

You can’t go wrong with a suit and tie. I always recommend my guys consider pulling out that suit you had to wear last time they were a groomsmen. Layer with a blazer and a fun tie, and you can even wear jeans with this look. Cozy sweaters layered over button ups are a great way to stay warm and stylish during the cooler months.

Rent the Runway
Banana Republic
J. Crew
Leather & Cotton
Jack Threads
Frank & Oak
Urban Outfitters

Don’t stress, you’re going to look great!

All-in-all, don’t fret too much about your outfits. You’re going to love your photos, not because of the colors you wore, but because you get to capture this special, and once-in-a-lifetime season with the person you love most.

For more inspiration on all things engagement session outfits, head over to my Engagement Session Outfit Inspiration Pinterest board full of outfits to inspire your looks!

engagement session outfit ideas, floral dress
engagement session outfit ideas, floral dress
engagement session outfit ideas, light blue dress and white shirt
engagement session outfit ideas
engagement session outfit ideas
engagement session outfit ideas
engagement session outfit ideas

What to wear to your engagement session

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