Towards the end of 2017, I discovered how much I enjoy photographing lifestyle headshot sessions for fellow entrepreneurs. Since doing so I've met so many amazingly creative people, which is something I'm so thankful for! I love being able to connect with them about entrepreneurship and small business challenges, as well as the victories we have to celebrate together! After booking a headshot session with me, the most common questions I receive from my clients are, "What do you recommend I wear for my photos? What colors and styles photograph best? Are there any patterns I should stay away from?" Luckily I've been photographing portraits for years, so I've picked up plenty of ideas for the best outfit styles and session planning tips!
Timing & Location
I’m a natural light specialist because I believe that natural light help to create photographs that feel fresh and timeless. Depending on the weather and sunny vs. overcast skies, I usually begin my headshot sessions 1-2 hours before the estimated sunset (a.k.a “the golden hour”) when the light is the dreamiest. Keep in mind that the sun sets much earlier during the colder months of the year and much later during the warmer months, so be sure to keep that in mind if you're taking off part of your work day or making plans after your session.
The location of your lifestyle session is up to you! If you need help deciding on a location, I’d be more than happy to recommend a few. There are plenty of great options around the state, and I’m always up for exploring a new spot together! In the past, some of my favorite locations have been the Old Campus at Yale University in New Haven, Connecticut, Harbor Point in Stamford, or Waveny Park in New Canaan.
Style Tips for Women
Dress it Up
Long, flowy dresses and skirts look amazing on camera because they bring extra movement to the photos. Especially when juxtaposed with nature, like the forest, plains or beach. Cute shorter-length dresses photograph beautifully as well.
When choosing colors for your outfits, I recommend selecting lighter tones and more muted shades. By avoiding ultra-bright, bold colors, it will help bring all the attention to your face! Shades of soft pink and muted blues, mixed with sophisticated light neutrals like heather gray, creams, leather brown and white* always photograph beautifully. This softer color palette fits beautifully into almost all natural outdoor environments.
*I do recommend to avoid wearing white as a main color (i.e. a plain white button down shirt). Instead, try pairing a gray and white polka dot sweater with a tulle skirt!
Flatter Your Favorite Features
Choosing flattering silhouettes and colors that compliment your natural features is the best way to ensure you’ll love the way you look in your photos! Three-quarter length sleeves create a wonderful slimming effect on all arms, so be on the lookout for an option with a longer length sleeve. You could also bring a cute jacket, blazer or cardigan along, too. Heels elongate women’s legs, making them look fabulous. Closed-toed shoes, heels in particular, look great on camera because they carry out the line of your leg all the way down to your toe. If your toes are showing in a peep-toe heel, consider treating yourself to a pedicure before your session!
No Spray Tan Needed
Although it might seem counter-intuitive, I recommend that you do not get a spray tan before your session, even a few days prior, because it tends to photograph orange even when it’s applied subtly and by a professional. Your actual skin tone will photograph the most beautifully!
Pairing an accessory or two with your outfit can really help bring some extra dimension to your images. Big statement necklaces bring a lot of pop to the photos, while the smaller, delicate ones are not as noticeable on camera. Belts, bracelets, and earrings bring great visual interest, so choose one or two that don’t compete for attention. If you want to add another level of dimension to your photos using accessories, feel free to bring along your favorite floppy hat, tote bag or even a bouquet of flowers! See how Rebecca and Sierra used some fun accessories during their sessions below.
Style Tips for Men
Mix It Up
You can never go wrong by mixing a suit coat, blazer or sport coat with a different pant color because it adds some extra visual interest to your photographs. I’m a big fan of this fresh take on a timeless classic.
Next time you walk by a store like J. Crew, you’ll notice the male mannequins and models are always wearing several layers at once. Adding another layer will bring extra dimension and visual interest to your photos. Blazers, vests, and coats up the level of any look. If the temperature is cool enough, you might even consider adding a v-neck sweater with a pop of color from a long-sleeved collared shirt and tie underneath. Don’t be afraid to get a little creative with layers!
Details, Details, Details
Long pants and closed-toed shoes are the most sophisticated and masculine looks for men. For your headshot session, I recommend leaving the shorts, sandals, and jeans at home. Suit pants, dress pants or colored pants work best. Brown leather dress shoes compliment almost every look, whether he’s wearing a full suit or a blazer and colored pants. Ties, bowties, pocket squares, colored socks, belts, tie clips, suspenders, vests, and watches are sharp compliments to any suit.
Are you ready to update your headshots? Send me a message at email@example.com so we can get a conversation started!