Choosing the perfect outfit for you and your significant other for an engagement shoot can be hard. You want your portraits in a gorgeous meadow or cobblestone courtyard to ‘look like us’, polished but effortless. Fashion forward, but timeless. However, putting together the perfect outfit for one person, let alone two people can be a tall order.

My boyfriend and I’s formal portrait session by When He Found Her
I recently had my own photos taken with Jon, my best friend, since we’re both turning 30 this year, together. I tried on 15 outfits, shared many different looks with my makeup artist, and emailed my photographer a moodboard. I definitely felt the pressure and stress to nail my portraits.
In this guide, I’m going to share with you the step-by-step tips that I’ve learned to simplify the process of picking a photoshoot outfit for real people that photograph beautifully, feels comfortably, and looks timeless. Of course fashion, and style are open to interpretation and personal tastes. I’m sharing tips I’ve found to consistent work for romantic, whimsical, outdoor engagement sessions.
Step 1: Brainstorm outfit ideas based on your location.
Where do you start when you have endless wardrobe options on Pinterest, the mall, and every online shopping site?
The single most important tip to looking good in your photos is to make sure your outfit is cohesive with the environment.
For example, if your engagement shoot is at the beach, I wouldn’t recommend wear a blouse and pencil skirt. It automatically looks out of place. Instead, I’d recommend a flowy dress that moves with the breeze over the water.
Similarly, at a cobblestone courtyard, I wouldn’t recommend a tropical tube top and mini skirt which looks out of place. Instead, I’d recommend a lady-like outfit with heels.
People intuitively know what looks right in a location, or doesn’t. Start brainstorming outfit ideas with your location in mind. I’ve shared a few outfit ideas on my Pinterest.
Step 2: Pick an outfit that is universally photogenic.
Based on my years of experience as a wedding and engagement photographer, there are a few features of dresses that photograph extremely well on real, non-model people. I highly recommend:
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- Defined waist – A dress with a defined waist so you look good at every angle, and define your hourglass shape. Dresses that are loose in the torso will create bumps.
- Flowy fabric – A dress that moves as you walk, and blows in the wind will photograph beautifully! It has drama without looking like you’re overly made up.
- Fitted torso – If you decide not to wear a dress, please ensure your outfit is fitted in the torso area.
So where do you find these dresses, aside from the mall?
- Rent formal dresses at Rentfrockrepeat.com
- I borrowed a self-portrait dress at Boro.it, also a local Toronto dress rental business.
Finally, what should you wear for shoes? Please wear shoes you can walk in. Do not wear stilettos and sink into the grass if you’re being photographed in a field, or vineyard.
Step 3: Finalize your partner’s outfit after you’ve chosen yours.
Please finalize your outfit before you decide on your partner’s wardrobe. The reason is because the two of you need to look good, individually, and together. So base the second outfit on the first one.
My top tip to helping your partner dress for the shoot is to choose an outfit that has the same level of formality. For example, I don’t recommend pairing polo t shirt and jeans with a floor length gown. It looks very out of place.
My second tip to ensure both of you look good is to limit your outfits to two or three colors that look good together. It looks more cohesive and deliberate, and stylish. For example, I chose white, and grey.
Step 4: Darken your lash line, and perfect your skin.
Makeup is a deeply personal choice, but two universal items that photograph beautifully are:
- Darken your lashline, which adds definition to the face
- Perfect your skin, especially under the eyes
If you’re hiring a professional, an elongated, neutral smokey eye with a soft lip is universally, and timelessly flattering. Of course, there’s also an option for a bold tip as a pop of color.
I deeply adore my makeup artist, Agnia:
Step 5: Balance your hair and face, eyes and lips.
The secret sauce for your style to look ‘effortless’, inspired by French girls and cool people everywhere, is to pick a lane:
- Eyes or lips – If your eyes are bold, go with a neutral lip. If your lips are bold, go with a clean eye.
- Hair or face – If you’re makeup is bold, pick effortless hair with soft waves. If you’re makeup is simple, go glam on the hair.
Step 7. Polish your nails.
Please apply 1 coat of nude nail polish. Your hands will subtly appear in the photos, or overtly appear since your ring will be photographed.
Step 8. The one thing nothing nobody does: Touch up your lip right before your shoot.
Please use your lip touch up that your makeup artist has provided. Your face is in every photo, and your lips is at least 10% of your look.
Then enjoy your photoshoot experience!
It’s really an unique experience to have your portraits taken, so once you’re at your photoshoot location, trust your photographer and don’t worry about your look. Have fun with your boo!
Jennifer Xu Photography offers engagement shoots with hair and makeup by experienced artists for a pampering, stress-free experience.
What do you think about these tips?
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