Engagement Sessions: What to Wear and Where to Go

A couple laughing on a quiet city street at golden hour
The point of an engagement session is to be photographed together <em>before</em> it counts.

An engagement session is a rehearsal. It’s the one chance to figure out how you look and feel in front of a camera together with zero pressure — so the wedding day isn’t the first time. It also gives you images for save-the-dates, the guest book and your home. Here’s how to get the most from it.

What to wear

  • Two looks. One dressed-up (a nice dress, a jacket), one relaxed (good jeans, a knit). It doubles your variety in one session.
  • Coordinate, don’t match. Same palette, different pieces. Matching outfits read as a school portrait.
  • Avoid tight logos and busy small patterns — they buzz on camera and date the photos.
  • Texture over pattern — linen, wool, denim, leather photograph richly.
  • Shoes you can walk in. Sessions move around.
  • Bring the ring cleaned if you want detail shots of it.

Long Island locations we love

Old Westbury Gardens and the grounds at Planting Fields for formal greenery and allees; the Sands Point Preserve trails and cliffs for a wilder feel; the beaches at sunset — Jones Beach, the Sound-side coves, Montauk if you’re going east; and the walkable downtowns — Huntington, Sea Cliff, Port Jefferson — for a warmer, lived-in look with coffee-shop stops.

A couple walking a quiet beach at sunset, silhouetted
Beach sessions want the last hour of light — and shoes off.

NYC locations that still feel personal

Everyone shoots the Brooklyn Bridge and DUMBO for a reason — they work — but the more memorable sessions use somewhere with meaning: the block where you had your first date, Central Park’s Bow Bridge and the Ramble, the West Village at blue hour, Grand Central’s main concourse, a rooftop bar you love. See our NYC photography page for more.

Timing is everything

Book the session to end at sunset. The hour before sunset (“golden hour”) is soft, warm and forgiving; the twenty minutes after (“blue hour”) give you city lights and moody skies. Midday sun is the hardest light of the day. Weekday evenings also mean fewer crowds at popular spots.

How to relax in front of the camera

You don’t have to know what to do with your hands — that’s our job. We’ll give you something simple to do (walk toward us, whisper the worst pun you know, keep walking past us) so you’re reacting to each other, not performing for the lens. The first ten minutes always feel awkward. By minute fifteen you’ll forget we’re there, and that’s when the real photos start — which is exactly the muscle you want built before the wedding.


Richard Black Studio covers weddings, Bar & Bat Mitzvahs, Sweet 15 & 16 celebrations and special events across Long Island and New York — photography, films and professional live streaming from one team. Tell us what you’re planning and we’ll send availability and a quote.

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