What to Wear to Your Engagement Photos || Milwaukee Wedding Photographer

What to Wear to Your Milwaukee Engagement Photos

Clothing is a great way to help show your personality and sense of style! But knowing what to wear for your engagement photos can be difficult. Here are a few tips and tricks I have learned as a wedding photographer that has helped my clients look their best.


Avoid anything too matchy-matchy, noticeable logos, graphics, neon colors, and bold prints. I recommend avoiding light wash or ripped jeans, shorts, t-shirts, and tank-tops as they tend to not photograph as seamlessly.


Make sure to choose clothing that you are comfortable in! A light, flowy dress or skirt that is able to catch the breeze can bring extra movement to the photos.

Choosing clothing that fits you correctly is key! Clothing that is too tight is uncomfortable, doesn’t allow you to move, and rides up or bunches during your session. However, outfits that are too baggy won’t let us show off your figure, and make you look wider than you actually are!

Coordinating, simple jewelry, and colors that are muted (think soft pastels if you want that romantic, airy look) or go BOLD and get a bold red or yellow dress for that punch of color against a blue sky. As for your shoes, just keep the location in mind when deciding between heels, wedges, or sandals.


Button-down shirts and sweaters are perfect! Just make sure that it’s all ironed or steamed to get out all those wrinkles. For pants, go for some chinos/dressy slacks or dark wash jeans. For shoes, a pair of brown or black dress shoes.


Feel free to plan multiple outfits for your engagement photos. Try picking a casual outfit and a dressy outfit. This is a great way to have variety, and show off your sense of style.

Most clients plan one to two outfits for their engagement session. I never limit the number of outfits, but remember that the more time you spend changing is less time we are able to be shooting.


When planning outfits make sure to consider the location of your engagement portraits. Choosing outfits with colors that clash with those of the existing environment will fail to make a cohesive looking portrait.

Think about the time of year. The light yellow-green of spring, deep greens of summer, and red-oranges of fall make for very different color pallets. Consider the season your engagement photo session is taking place when you are picking your outfits.


Plan your outfits down to your shoes, socks, jewelry, and a matching belt! This might mean you bring extras for each outfit, but details matter when it comes to engagement images!

In addition, switching out small accessories (i.e. jackets, hats/headbands, etc) is an easy way to add variety to your images within a portrait session.


If you want to wear your glasses in your engagement portraits, think about popping out your lenses or borrowing empty frames from your optometrist. This is the best way to avoid glare or distortion that eyeglasses can cause in portraits.


Use a matte foundation and concealer. Shiny or shimmery foundations may make your skin look oily, so I recommend you avoid them!

Avoid products with zinc oxide or titanium dioxide. These cause makeup “flashback” that leaves a white powder residue in images with flash. Google “celebrity flashback photos” to see examples of what can happen, and why to avoid it!

Go natural when it comes to your makeup. While you may need to add a little extra mascara for the camera, don’t go too heavy!

I often recommend wearing your hair down with soft curls, waves, or even straightened as long as it has movement. I want you to be able to shake and flip your hair around!

Hiring a professional hair and makeup artist can help you look naturally glowing and your very best. If you need help finding one, I would be happy to give you a few recommendations.


You’re more than welcome to bring your dogs to your engagement session! I love animals and am happy to have them there. This usually works best if you have a third person who is able to come along on the session to help your pup during images that don’t involve them. Another way is to arrange a pup pick up time about halfway through the session 🙂


  1. Try on your outfits to make sure everything fits, you feel comfortable, and have everything you need ready to go. Make sure your bra straps aren’t showing with any of your chosen tops.
  2. Iron and hang your clothes for the drive to your session. This will prevent wrinkles.
  3. Don’t wear a hat or headband on the way to your engagement portraits. No one loves hat hair!
  4. Hairspray the part of your hair to prevent flyaways. Sounds silly, but this simple trick makes a HUGE difference for longer hair.
  5. Check your nail polish for chips, and do a last-minute touch-up.


Still sure where to start? When in doubt check out my What to Wear Pinterest board for inspiration!



Hi! I am Ali Bergen, a wedding and portrait photographer specializing in timeless and joy-filled imagery. I photograph weddings and portraits in Milwaukee, Hartford and all around the great state of Wisconsin.

Say Hello & Let's Connect!

Featured Categories