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A couple sitting on a wooden staircase in front of an house with their dog showing off one style of casual engagement session outfit ideas.


Engagement Session Outfit Ideas and Tips from a Photographer

October 6, 2023

Looking for some engagement session outfit ideas for your photoshoot? I’ve got you covered.

Engagement photoshoots are an amazing way to celebrate you and your partner and the journey you are about to embark on together. However, picking the right outfit can sometimes feel super overwhelming. 

Well, as an engagement photographer myself, I have captured my fair share of engagements and have plenty of tips for engagement session outfit ideas.

Whether you are looking to keep it casual, dress up a bit, have an outdoor session, or anything in between, these engagement session outfit ideas should help point you in the right direction. 

Engagement Session Outfit Ideas 

Casual Outfit Ideas

A couple holding hands and walking across a parking lot with overgrown trees behind them.

If you’re not someone who generally dresses up and is more comfortable in casual clothes, lean into that with your engagement session outfit. Now, this doesn’t mean that you need to wear gym shorts and a T-shirt. Here are a few of my top recommendations for casual outfits that will also look amazing. 

For Outdoor Sessions 

An engaged couple holding hands and smiling while standing in a field with overgrown grass and green trees behind them.

If you are planning an outdoor session, things like linen button-up shirts, khaki or linen shorts, sun dresses, or loose, flowy t-shirts are all great options. These all have a casual yet intentional look to them, and you can even accessorize them with things like jean jackets, unbuttoned shirts, and sunglasses. 

For Warm Weather Sessions

A couple kissing while standing in the street of a small city.

If the weather is a bit warmer, outfits like flowy dresses, jeans or jean shorts, crop tops, and loose, airy shirts will all look amazing. You do want to make sure you check the weather if it is going to be really hot – it may be better to wear jeans or khaki shorts over pants on these days. 

Whatever you choose, it’s important that you don’t wear clothes that are super thick or very heavy. Those clothes combined with the warmer weather don’t always make the best combination. 

For Cool Weather Sessions

A couple smiling with their arms around each other as they walk in a wooded area in winter.

If you are looking for engagement session outfit ideas for when the weather is a bit cooler, you have a few more options because you can layer your outfit. 

Jeans or casual pants and longer-length skirts are a great place to start. For tops, you can go with plain T-shirts with a jacket on top. These can be leather jackets, jean jackets, sherpa-lined jackets, or even a plain hoodie with another jacket or flannel on top! 

Dressy Outfit Ideas 

A couple sitting on the ground laughing as one haas their arm over the other's knee.

If you love dressing up or want to take this opportunity to dress up more than you normally do, there are plenty of options for you that you will still be super comfortable in! You can also elevate all of these outfits by adding accessories like watches, jewelry, bags, and nice shoes. 

For Outdoor Sessions

A woman with her arm looped through her partners as she rests her head on their shoulder in a garden area.

For a dressier option for outdoor sessions, you can lean more towards longer-length, flowy dresses (instead of sun dresses) and swap out your shorts for full-length pants. For tops, you can opt for dressier, airy blouses, long-sleeved button-down shirts, or polos. 

The key to remember here is that dressy doesn’t necessarily equal black-tie formal. You don’t need to wear a full tux or an expensive gown. You can find outfits that look amazing but that aren’t super expensive. 

For Warm Weather Sessions

A couple holding hands and looking at each other as they walk on a small landing at the bottom of a staircase.

For warmer weather sessions, I would still suggest opting for pants over shorts. You can wear nicer, slim-fit dress pants or opt for more flowy linen pants. Pairing these with either a plain, short sleeve button-up or a long sleeve button-up is always a great idea. 

If you want to add a bit more flair, you can either opt not to button the shirt up all the way or throw a matching jacket on over it! 

If you would rather wear a dress, you can go for one that is a little more fitted than a casual dress. These can be shorter, full-length, or a matching skirt/top combo. 

For Cool Weather Sessions

A couple laughing while sitting next to each other on a brown leather couch in a coffee shop.

For cooler weather sessions, I would definitely recommend finding something that is a bit more full-length. This can be things like suits, full-length dresses, or dresses with sleeves on them. 

For the suits, you have a couple of different options. You can wear jeans with a jacket and button-up shirt, a matching pant/jacket combo with a button-up, or you can even opt for a plain t-shirt or turtleneck under the jacket. 

Another great option for cooler weather is sweaters. These can match great with jeans or dress pants. You can even throw a longer jacket on over it or wear a button-up underneath it! 

Engagement Session Outfit Tips 

Wear something you are totally comfortable in 

A woman sitting on the edge of a kitchen island as she leans back into her partner who was one hand around her stomach and is holding a drink in the other.

My biggest tip when it comes to engagement session outfit ideas is to find one that you are totally comfortable in. This can mean picking something from your own closet or just choosing pieces of clothing that you are used to wearing. 

If you’ve never worn a full suit or a sweater before, make sure you can actually move around comfortably in them before you decide to wear them for your session. If you are stiff or uncomfortable in your outfit, it can show through in the photos, which is the last thing we want! 

Buying a new outfit is great and can make the pictures feel extra special. However, my recommendation would be that you try it on a few times before your session. You can even wear it around your house for a bit just to make sure you are totally comfortable in it before you take your engagement photos! 

Bring layers if the weather is cooler 

A couple walking along a wide path in a park while holding hands.

You’ll notice a lot of the cool weather outfit ideas include different layers. This is super important, especially if you are planning to be outside during your session. Make sure when you are planning your outfit you find things like jackets, sweaters, scarves, or gloves that can go along with your outfit. 

You also want to keep the weather in mind when you are picking out your shoes. If it is going to be really cold, you may want to find closed-toe shoes or make sure you can wear some sort of socks or leggings so your feet don’t freeze! 

Coordinate your outfits 

A couple with their arms outstretched holding hands and walking up the side of a grassy hill.

Make sure you and your partner coordinate your outfits. Now, this does not mean that you have to match in any way. Instead, try finding complimentary colors that you can wear that play off of each other. 

You can always find accessories or small pieces that you can add to your outfit that match the color your partner is wearing. 

You also want to make sure that you are on the same page for how dressed up you want to be. It may look a bit awkward if one of you is fully dressed up, and the other is in shorts. If you don’t want to be fully on one side or the other, you can also meet in the middle.

For example, you can dress down a suit by ditching the jacket, opting for a t-shirt over a button-up, and swapping out dress shoes for a pair of plain white sneakers! 

Be conscious of colors and patterns 

A woman sitting on a stool as she laughs and has her arm around her partner standing next to her.

Finally, you want to make sure you are conscious of the colors and patterns you are wearing. When you are picking out your outfits, make sure you are thinking about where you are going for your session and what the backgrounds behind you are going to look like. 

If you are going to be in a field of flowers, you may want to avoid floral patterns. If you are heading into the city to take pictures in front of brick buildings, you may not want to wear red. 

Whatever you choose to wear, you just want to make sure that you don’t blend into your background or wear a color or pattern that is going to be overly distracting. 

Final Thoughts on Engagement Session Outfit Ideas

Hopefully, these engagement session outfit ideas and tips will help you plan out the perfect outfits for you and your partner. Above all, you want to make sure that you are comfortable and confident in what you are wearing.

These photos are for you, not anyone else, so you get to choose whatever type of outfit and vibe you want! Now that you have some great outfit ideas for your engagement session, all you need is the perfect photographer to capture it.

If you are still looking for that person, click here to learn more about my services, or get in touch to talk about how we can make your dream engagement session a reality!

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Photographer, amateur snowboarder, dive bar connoisseur,  inspired by music, good movies, and you.

I'm a Charlottesville wedding photographer and I specialize in capturing wedding days with a documentary approach. Love is pretty rad, and your photos should be, too.