7 Chic, Elevated Engagement Session Outfits – What I’d Wear Inspiration

It’s time to schedule your engagement session! Your engagement session is not only a perfect opportunity to showcase and capture this exciting time in your life but also to showcase your unique styles. I love photographing my couples in downtown areas and cities. They’re always so full of inspiration and beautiful architecture. Whether it’s a downtown engagement session in Chicago, New York City, Charlotte, DC, or LA, you’ll want to choose outfits that not only reflect you but reflect the chic and elevated vibe of the urban setting.

General Engagement Session Tips

  1. Consider Your Location: This is the first step. For these examples, if you’re in a big city, you’ll want to opt for chic and sophisticated outfits that complement the landscape. Think sleek dresses, tailored suits, and stylish accessories.
  2. Mix and Match: One way to add visual interest to your engagement photos is to mix and match different textures and patterns. Don’t be afraid to experiment with different combinations.
  3. Stick with a Cohesive Color Scheme: Choose colors for your engagement session outfits that create a cohesive look that is both stylish and elegant. Shades like black, white, gray, and navy blue will always be a perfect, classic go-to
  4. Dress for the Weather: Always keep the weather in mind when you choose your outfits. Comfort is the top priority so it doesn’t show through on camera. Ensure you’re wearing light, breathable fabrics in teh summer, and layering up in the colder months. Then you can bring in color with accessories.

City Chic and Elevated Outfit Inspiration

You’ve got an engagement session in New York City, Chicago, or DC and aren’t sure what to wear. You may want to consider dressing chic, elevated, and elegant. This will help you match the sleek and elevated city aesthetic, bring confidence, create a timeless look, and set the tone for your wedding. Below are some to help get you started!

City-Chic, Elevated Outfit Inspiration #1


Black Dress – Anthropologie Significant Other Demi Backless Long-Sleeve Column Gown

Black Heels – Stewart Weitzman Nudistcurve Ankle Strap Sandal

Earrings – Bauble Bar, Addie Beaded Drop Earrings

Suit Jacket – Tech-Smart Trim Fit Stretch Wool Sport Coat from Nordstrom

Watch – Movado Bold Evolution Mesh Bracelet Watch, 40mm

Shoes – Dino Penny Loafer from Nordstrom

Engagement Session Outfit Inspiration #2

Green Dress – Reformation Aude High-Neck Midi Dress

Heels – Stuart Weitzman Stuart 100 Pump

Earrings – Metal Flower Drop Earrings

Men’s Dress Shoe – Allen Edmonds Park Avenue Oxford

Men’s Belt – Montblanc Horseshoe Buckle Leather Belt

Men’s Suit – Indochino Hamilton Sharkskin Blue Suit

Men’s Undershirt – Drake’s Oxford Cotton Button-Down Shirt

Men’s Pocket Square – Cufflinks, Inc. Green Floral Silk Pocket Square

Engagement Outfit Inspiration #3

White Dress – Michael Costello x Revolve Sara Gown

Blue Heels – Badgley Mischka Sacred Bow Pump

Bracelet- Effy Diamond Tennis Bracelet

Earrings – Oscar de la Renta Cabochon Dome Earrings

Blue Jacket – Ted Baker London Jay Slim Fit Jacket

Grey Pants – Canali Men’s Lightweight Flannel Trousers

White Sneakers – Jace Sneaker from Nordstrom

Elevated Engagement Session Look #4

Pink Suit Dress with Cape – Katie May Boss Lady Dress from Revolve

Green Shoes – Jessica Rich Ankle Tie Pointed Toe Pump

Gold Hoops – Argento Vivo Chunky Gold Hoops

Men’s Suit – Indochino Hamilton Sharkskin Blue Suit

Pocket Square – Ralph Lauren Purple Label Ainsley Choppa Print Silk Pocket Square

White Sneakers – Jace Sneaker from Nordstrom

Black Dress – Michael Costello x Revolve Mr. Gibson Mini Dress

Black Heels – Badgley Mischka Blaze Pump

Stud Earrings – Swarovski Constella Stud Earrings

Men’s Blazer – L.B.M. 1911 Cotton Herringbone Sport Coat

Men’s Belt – Shinola LIghting Bolt Keeper Leather Belt

Black Boots – BOSS Libson Chelsea Boot

Engagement Session City Look #5

Red Gown – Bronx and Banco x Revolve Leo Maxi Dress

Tuxedo – David Donahue Classic Fit Tuxeo

Men’s Dress Shoe – Cole Haan Hawthorn Oxford

Nude Pumps – Jimmy Choo Love 100

Earrings – Gold Hoop Earrings

Necklace – Cartier Amulette de Catier Necklace

Colorful, Chic Outfit #6

Orange Dress – Anthropologie Delfie Collective Strapless Silk Fringe Dress

Blue Suit Jacket – Express Light Blue Linen Suit Jacket

Blue Earrings – Blue Statement Earrings

Brown Pumps – Sam Edelman Hazel Pump

Men’s Loafers – Ferragamo Ree Bit Loafer

Elevated, Chic Outfit Inspiration #7

Dress – Amsale Pryce Off-Shoulder Satin Gown

Heels – Stewart Weitzman Nudistcurve Ankle Strap Sandal

Earrings – Deepa Gurnani Warren Crystal Drop Earrings

Watch – MOVADO Bold Quartz Silver Dial Men’s Watch

Tuxedo – David Donahue Classic Fit Tuxeo

Belt – Leather Black Belt

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