What to Wear for Engagement Photos (If You Love Thrifting, Vintage Style, and Unique Outfits)

Let’s get something straight: I’m someone who loves all things vintage, quirky, and a little offbeat. And as a Chicago engagement photographer, that’s the kind of energy I want for all my sessions. So if you’re engaged, anything like me, and planning a session that feels different from the rest, you might be wondering what to wear for engagement photos. Because your engagement photos don’t have to look like everyone else’s. They should feel like you, babes! That’s what this guide is all about, so keep reading to find some ideas for engagement photo outfits that actually fit your vibe. 

What to Wear for Engagement Photos | Engagement Photo Outfits That Are Anything But Boring 

If you’re here, you probably spend more time at the thrift store than you do at home and love anything that has retro vibes or bold colors. And your Chicago engagement photos are the perfect time to let that style shine. Where most people find a cute white dress and call it a day, you probably want more. Something vintage, textured, or just ultra-funky is probably more up your alley. Sound right? Here’s exactly how to decide what to wear for engagement photos. 

Dress Like Yourself

The best thing you can do is wear something that actually feels like you. Not what you think engagement photos are supposed to look like.

For a long time, everything about weddings has been ruled by tradition, from the time you’re engaged until the time you say “I do.” And as a Chicago engagement photographer, I literally could not be happier that we’re in the era of non-traditional weddings and days that are deeply personal. That carries over to your whole engagement, so engagement photos that feel like you? Yeah, that’s in. 

My top tip when you’re deciding what to wear for engagement photos is to be fully yourself. Don’t bend to put yourself into boxes that you don’t fit in! If you want to wear white, absolutely go for it, but don’t feel like you have to. The same goes for wearing a dress. 

You’ll always feel at your best, and therefore get the best photos, when you’re wearing something that makes you feel comfortable and confident. 

Don’t be Afraid to Add Color (In Fact, Please Do)

Color always gets a yes from me. Whether you’re decked out in a monochrome outfit or just adding pops of color in through your accessories, know that I’m gonna love it. 

Looking for pops of color? Here are some things that kill it with a white outfit every time: 

• Fun shoes, like these Dolce Vita Cleo Sequin Heels, these Charlotte Stone striped heels, or the Heart Leatherette Slingback Heels from Unique Vintage
• The Lovebug Veil or Venus Veil from Madison Chamberlain 
• Maximalist jewelry, like these Ribbon Hoop earrings from AtPresent
• A super rad bouquet with vibrant colors

Go Couture

There are my funky vintage people and my high-fashion vintage people, and if you’re the latter, let’s talk couture pieces. You can definitely take a classy route without compromising personality, trust me. I see it done all the time when these kinds of people are wondering what to wear for engagement photos. It always turns out to be something like a vintage satin slip dress or a 90s Chanel two-piece set that I literally cannottt get over. 

Consider the Weather

Chicago weather can shift quickly, so planning your outfit around the season makes a big difference.

What to Wear for Engagement Photos in the Fall or Winter

Fall and winter, obviously, bring chillier weather, so my best tip is to add some textured layers. Think fur coats, leather gloves, and animal-print scarves. 

What to Wear for Engagement Photos in the Spring or Summer

Warmer weather means you get a solid base layer to accessorize around. For spring, you can do skirts and boots (a look I always love), and summer should bring light fabrics that let you breathe, like chiffons and organzas. Because trust me… No one looks their best when they’re burning up. 

Outfit Changes

Let’s talk outfit changes, because they’re honestly some of my favorite things ever, especially for engagement photos. One classy look and one casual look? Love. Want a groovy look, but not for every picture? That’s fine, let’s make a change! 

Outfit changes are a great way to add some variety and a little bit of fun to your photos. So if you don’t want to fully commit to the retro, funky look, don’t fret. Wear one outfit for one location and one for another. 

Engagement Photo Outfits I Adore

I keep a running list of outfits I’d love to photograph, because what to wear for engagement photos is one of the most common questions I get. So I’m always on Pinterest, saving cute outfits for you guys. Here are some I have saved to throw your way:

• The Ivory Lovespell Dress by Selkie for a cottagecore-themed shoot
• The Dela Two-Piece Set by Reformation for classy vintage vibes
• The Rosalinda Dress by Club L London for a statement
• This sequin green dress by ASOS for funky disco energy
• Or for something simpler, Landon by Jenny Yoo paired with some crazy-fun accessories 

Where to Take Your Funky Engagement Photos in Chicago

Now that you know what to wear for engagement photos, let’s talk about where to take engagement photos because… Chicago is crawling with editorial playgrounds. You can check out my comprehensive guide to Chicago engagement photo locations for every style, but here are a few that consistently serve groovy-goodness: 

• Chinatown (and if you don’t believe me, check out Natalia and Jaekeun’s session)
• Any dive bar (and yeah, you know I have some inspo) 
• The Chicago Art Institute, because it delivers every single time

Wren and Rose | Your Funky Chicago Engagement Photographer 

Have a vision in mind? I’d love to hear allll about it. Inquire here, and we’ll start planning an engagement session that feels totally unique to you.