Stylish Urban Chicago Engagement Photos | Tamera + Sam

September 16, 2022

Tamera + Sam met up with us in Chicago for their engagement shoot & can we just say: dayyummm these two made our job easy🔥🔥 It’s been a few months and we still can’t get over these stylish AF Chicago engagement photos. 

From exploring downtown & meandering along the Chicago Riverwalk to taking in the iconic skyline views from North Avenue Beach, these two put on an absolute SHOW for everyone around. 

Ready for us to show ‘em off to you? 😉

couple holding hands on stairs

About the Couple: Tamera + Sam

Now first, we have to talk a little bit about the couple themselves because they are two of THE coolest people we’ve got the pleasure of working with.

Sam is a guitarist + songwriter who performs all over Chicago, and Tamera is a US Army Officer – talk about a power couple! She joined ROTC at 25 years old, enlisted in 2019 on a whim (and surprised everyone in her family), and graduated with her Masters of Healthcare Administration. AKA a total badass.

These two hotties got engaged at the Sears Tower on 11/21/21 – so you know we had to include views of the tower in their engagement photos – and will be saying their “I do’s” in August of 2023. We can’t wait to see all the amazing things that they continue to do together and are so grateful we connected with them!!

couple kissing buildings

An Awesome Day Exploring Downtown Chicago

Stylish Chicago Riverwalk engagement photos

When everyone around you is looking at you like you’re photographing a famous couple, literally asking if this shoot is for a magazine, you know they’re killin’ it 😂

Seriously: just imagine walking down the Chicago Riverwalk, minding your own business, and suddenly you see Tamera + Sam, dressed to the max, looking like straight up runway models together. Your jaw would be on the floor, too!

We started off this Chicago engagement session at the Riverwalk, one of the most popular pieces of downtown where you can walk (hence the name – creative, right?), stop at a restaurant or bar, kayak down the waterway, and see beautiful views of the city. We looove photographing Chicago Riverwalk engagement photos because of the huge variety of location options + backdrops!

First, Tamera + Sam enjoyed a few minutes relaxing on the stairs leading down to the water, before finding a spot to look out at the Riverwalk & enjoy the views. From there we headed into the downtown area, bustling with massive buildings, tourists everywhere, and cars driving every which way – yet somehow, these two managed to focus the city spotlight completely on them. Standing in their killer beige + white outfits, lovin’ on each other, and looking like Vogue models doing an editorial photoshoot: what more could you ask for from a downtown Chicago engagement shoot?!

Iconic skyline views from North Avenue Beach

Once we were done in the city, we ventured over to North Avenue Beach to get those iconic Chicago city skyline views – a must-have for any Chicago engagement photos. Walking along the blue waters with the open sky + skyscrapers in the backdrop is breathtaking, especially when you’re dressed to the absolute nines like Tamera + Sam were! This is definitely one of the best locations in Chicago for engagement photos. Plus, we got the Sears tower in the back of these photos, which adds an extra special level of meaning since that’s where these two got engaged in the first place!

Chicago engagement photo outfit inspiration

Have you ever seen a more stylish couple than Tamera + Sam?! We always tell our couples that we recommend bringing one or two outfit changes for their engagement photos to add some variety, and these two took it to the next level.

Tamera started off with a minimalist look, rocking a simple white, high-neck tank, tucked into some absolutely gorge beige pants. Sam coordinated his look with hers, also keeping it simple with a collared white top, khaki shorts, and white Converse. This first outfit pairing goes to show how rad you can look if you keep your outfit simple, especially when you’re in the city with lots of colors + textures around you to add to your photos!

couple walking on sidewalk

Once we were at North Ave Beach to take in those breathtaking skyline views, Tamera changed into a dark tan ribbed dress with a long tie in the front for some added flair, plus a leg slit for some extra spice. Next to Sam in his white top + tan pants, she looked freaking flawless!

And finally, they ended the evening with one last outfit change, Sam staying in his white button-down + swapping the dark tan pants for light beige ones, and Tamera switching out her dress for a cream-colored strapless one. With every single outfit change, these two looked like they belonged on the damn front cover of a magazine!

We are sooo thankful we got to capture Tamera + Sam’s Chicago engagement photos at the Chicago Riverwalk, downtown Chicago, & North Avenue Beach. They’ll forever be some of our favorites!!

couple holding each other chicago skyline

The talented creative team

We can’t wrap this up without shouting out the wonderfully talented people who contributed to making this Chicago engagement photoshoot as stunning as it was. If you need a hair braider, makeup artist, or nail tech in the Chicago area, look no further than the awesome people below who helped out with these photos!

Chicago Braider: Braid Me Up Lenna

Chicago Makeup Artist: Blush and Britt

Chicago Nail Tech: Beyoutiful Nails by Lilly

Chicago Engagement Photo + Video Duo: Elope With TKM (yours truly😉)


Engagement + Elopement Tips and Resources

If you’re engaged like these two, or an engagement is on the horizon, be sure to check out the engagement + elopement resources we’ve got for you below!

10 Best Things to Do After Getting Engaged (And What Not to Do)

60 Unique Elopement Ideas for Your Dream Elopement Day

Our Top 20 Elopement Planning Tips + What Not to Forget

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