9 Tips About What to Wear to Your Engagement Session

May 5, 2025

When it comes to selecting your engagement session outfits one of my favourite tips is to think of your engagement session as a date night. This includes clean clothing in good condition without tears or rips and shoes that are free of scuffs and stains. But there are exceptions to every rule, if you’re a very active couple and a gym date is more your style, fitness apparel makes sense. If your ideal date night is pizza and wine on the beach, then flowing and lightweight materials are a great choice with shoes optional.

You might be feeling some nerves about being in front of the camera, but you also might be worried about what to wear for your session. Below is a list of 8 clothing tips to help you build your engagement session outfit.

9 Tips About What to Wear to Your Engagement Session

 

1. Confident and Comfortable

During your engagement session, you want to feel good in the clothing you have on, and it’s important you choose outfits that you are comfortable in. Choosing an outfit you’re unhappy with, and that matches your body type, can completely ruin your engagement session experience and you will always remember it when you look back on your images. This is why it’s so important to pick clothes that make you feel Confident and Comfortable!

Selecting the right undergarments is just as important when selecting your final outfits. For women, it’s incredibly important to pick undergarments and shape wear that fit appropriately, choose pieces that don’t cut into your thigh, waist or shoulder, and ensure they stay in place during your session. There’s nothing more distracting than a dark pair of shape wear peaking out as you walk, spin or sit, which is why it’s important to match your undergarments to your skin tone and to make sure you test your complete outfit on to make sure there are no wardrobe mishaps.  For men, it’s important to avoid wearing a dark undershirt under a light dress shirt or polo, and if you’re opening up a few buttons, it’s best to choose a V-neck undershirt option instead of a crew neck.

While buying a new outfit can be fun, there’s a good chance you have some forgotten gems in your closet too. Before you head to the store to buy a new outfit, let your partner go through your closet and pick out several outfits that they feel you look great in – you might be surprised! If you feel completely lost when it comes to choosing an outfit, hiring a professional stylist is a great option too. A quick search for “Personal Stylist Near Me” is a great place to start to get an experts opinion on selecting the right outfits for you.

2. Coordinate and Compliment

I’m a firm believer that there is a time and a place for everything. So if your engagement session theme is ‘awkward couples photos’ then let’s commit to it and bring out those bold and vibrant patterns or matching outfits, but for most couples, complimenting your partner is the best rule to follow with selecting outfits for your session. What does this mean? Well there are classic combos such as blush and navy, cream and blues, or soft florals with earth tones, but one of the best ways to pick out outfit colours is to use a colour wheel. Pick softer versions of complimentary colours (avoid vibrant and neon versions), or choose patterns with subtle pops of colour so your outfits add interest to your images but don’t steal the spotlight from you and your partner.

Pinterest is a great resource for outfit inspiration, and searches such as “couples clothing style guide” and “engagement outfit style guide” are a great place to start. You could also check out these blog posts by Style & Select for great outfit guides and tips.

3. Patterns, Colours and Textures

Patterns can be fun and add interest to your images, but there is this little thing called ‘moiré’ which is the bane of your photographers existence. Moiré is cause when your cameras sensor encounters a pattern that conflicts with the resolution of the device. All that is to say that fine patterns and repetitive details like houndstooth, narrow stripes, gingham, or fine herringbone are the biggest causes of moiré in your images and it is recommended to avoid them.

Black and white are a classic outfit combo, but other clothing options that photograph well together are pastels, cool colours, and neutral tones. They tend to be the most complimentary to skin tones and aren’t too distracting from you and your partner as the subjects of your images. Remember, this session is about you and your partner, and your outfits should contribute to the vibe of your session, enhance your confidence and help you feel comfortable. Opt to include pops of colour in your accessories instead of your outfit, and please skip the neon colours! Also, choose forgiving fabrics. There’s nothing worse than looking amazing as you leave the house and then once you’ve stepped out of your car you realize that your outfit leaves you looking disheveled with wrinkles from head to toe.

Textured clothing is a nice addition to your outfit options and can be subtle or strong depending on what you choose. To add some visual texture and warmth to your outfits look for clothing or accessories that include lace, leather, tweed, faux furs and more – just avoid the moiré!

4. Accessories 

Accessories are a great way to add style, personality, colour and texture to your photos and to enhance your outfits. Think along the lines of a faux fur wrap or a leather jacket to add texture and visual interest, or a patterned scarf, necklace, socks or tie to add a pop of colour to your images. It’s important to choose items that can be slipped on and off easily to give yourself a variety of looks.

5. Think of The Season

We’re lucky in Windsor-Essex that we have all four seasons, which gives you an extra element to personalize your engagement session. If you love winter activities, then a winter engagement session would be a great choice to show off what brings you together, or if you spend a lot of time outdoors during the spring and summer, you might have tan lines that you should be conscious of while choosing your outfits. Those dreaded shirt sleeve lines on your arms, AKA ‘farmer’s tan’, or lines from wrist watches, sandals and hats can also be very distracting in your engagement images, so it’s a good idea to plan ahead and make sure your clothing choices cover these things. Other distracting items in your photos are your pockets – which are very handy for every day life, but can be a big headache during your engagement session with awkward bulges from keys, wallets and phones.

Think of the seasons when picking your outfits and choosing any props or accessories. Layering clothing and using tones that match the seasons will add extra personal touches to your photos. Earthy tones look beautiful during fall months, while light and bright colours are lovely for spring and summer. Small blankets to wrap yourselves in are always a great idea, and can add character to your session along with some much needed warmth on chilly days.

6. Switch Up Your Look – Wardrobe Change

During the planning phase of your engagement session, check with your photographer to see if a wardrobe change is possible. I love wardrobe changes, especially when couples switch from a more casual look to something more refined and chic! Your dressier outfit doesn’t have to be a suit and tie, but think along the lines of an upscale restaurant or to a friend’s wedding. For your casual option a nice midi dress/day dress is a great choice, while a button up shirt or polo with some nice slacks and a nice pair of dress sneakers.

7. Make it Black Tie – Take it to Another Level

Your engagement session is a perfect opportunity to get fancy – I mean real fancy – and have fun with your wardrobe choices. When in doubt, dress it up, not only will it give you a confidence boost, but it will also add a level of sophistication and style to your engagement session images. Most of us have a fancy outfit or two collecting dust in our closets, so dust it off and bring it out for your session, but if you want something new try a rental option like Rent the Runway so you won’t have to add one more outfit to your closet, and can rent it for a few of days and send it back when you’re done! Both options make it easy (and more affordable) to access high-end looks that you may only wear once.

8. Opt for Classic Rather Than Trendy Looks

Fashion is cyclical, and trends come and go, so it’s best to opt for clothing that is classic and avoid trendy looks. Classic and timeless pieces have elegant and flattering silhouettes, and use high-quality materials like a nicely tailored pair of pants, blazer or button down, or a fitted dress, skirt or pants. You want to look for materials and stitching that would give you years of wear, not months or a few washes and then fall apart. Choose items that focus on simplicity, neutral colours, and clean lines. Neutrals like black, white, grey, beige, and navy blue, are a great foundation for building outfits, and remember, you can personalize these choices with accessories and textures to give you comfort and confidence in your photos.

9.  There Are Exceptions to Every Rule

Are all of these tips going to work for you and your partner? The key is to be true to yourselves, feel confident and comfortable, and have fun! Match your outfits to your session vibe, and just enjoy the process. Now let’s talk more about your Engagement Session!