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Maui Tips · Photo Shoots ·  Island Life · Styling Inspiration

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A Stylist and Photographer’s Guide

There are two questions I almost always get asked by clients…

  1. What do we do if it rains? –> See my blog post on that topic here.
  2. What should we wear?

Choosing what to wear for your Maui family portrait can be super overwhelming! 

You want your kids and yourself to feel comfortable and like yourself, but more put together. You want the clothing not to be fussy and stand up to the wind and sand and water. And you want all the outfits to look good individually, and together, but without being to matchy-matchy.

Boy! That’s a long list! But don’t worry, here are some general DOs and DONTs to get you started on picking the perfect outfits for your family photo session here on Maui.

Family dressed up in pastel colors for photo session on Hawaii

DOs – Best Wardrobe Styling Practices for Family Beach Portraits

> Comfort. Choose something your kids have worn before and feel comfortable in. If your little one has never worn a romper or ruffles before, this is not the time to find our that she hates them.

This also goes for mom and dad. If you like the idea of a strapless dress, but notice that you end up fussing with it all the time, because you feel slightly self-conscious (that’s me), then save it for another time. We want you all to focus on each other and have a great time at the session!

> Be the star! This one’s especially for moms. Pick a dress or garment because it makes YOU look good, not because IT looks good.

Sometimes you’ll need another set of eyes to decide this, but most often you’ll know because you think “I feel great wearing that dress.” versus “That dress is so beautiful.”

> You want durable & hassle free. For little ones, pick fabrics that can stand up to the elements–especially important if we’re shooting at the beach on Maui. Invariably they’ll end up squatting down to dig in the dirt, really no matter where we are, so be prepared.

Choose something that doesn’t wrinkle already on the drive to the shoot.

Secret Stylist’s Tip No. 1

Swimwear is a secret weapon and perfect match for a beach shoot. It will stand up to water and sand and doesn’t wrinkle.

For boys you can find beautiful patterned or solid-colored trunks and add a white shirt (cheap and easy to buy and bring a backup).

For girls, swimsuits can make a great base upon which to layer wrap skirts, dresses, kaftans. And white swimwear will usually stay white at the beach. 

Secret Stylist’s Tip No. 2

Fabrics that flow and can be draped looks especially beautiful in photos, because they add movement and texture. Look for skirts or dresses made out of light fabrics like silk, chiffon, or rayon.

DOs – More Tips on What To Wear To Your Maui Beach Portrait

> Bring backups. I’m not a fan of outfit changes to get different looks. In my experience it adds stress and takes time and energy from the session. Plus, in an album or gallery the photos will be less cohesive. A change tends to draw focus to the clothing as opposed to the people.

But it’s nice to have backup if something doesn’t work or has gotten dirty or overly wet. A simple white shirt doesn’t cost much and doesn’t take up a lot of space but you might be glad to have it.

> Accessorize! Take a neutral, pastel, perfectly nice but boring wardrobe set and add your own personality and some pizzazz to it! Sprinkle in some pompoms or maybe some raffia accents for flavor. Most importantly have fun with it!

> Think about the location when picking your outfits. For instance, choose colors from the beautiful hues of the ocean at sunset. That doesn’t mean it has to be blues.

Neutrals such as soft pink, peach, cream, muted purple, and beige all photograph extremely well. They blend effortlessly with the natural elements rather than competing with them. 

> Pick your level of formality and keep it the same for all members of the family.

If you are going for casual, make sure everyone is dressed in shorts and summer dresses.

If you opt for a more dressy look with a glamorous dress, then dad has to step it up with slacks or even a suit. Formal wear adds an unexpected zing and looks amazing in natural surroundings, such as beaches, rocky outcrops, and forests!

Golden hour family outfit inspiration for a formal Maui beach photo session

Secret Stylist’s Tip No. 3

Hats! Hats! HATS! Hats are amazing! The right hat can instantly dial up the glamor factor of any outfit! Instead of merely wearing a dress, you’ll be wearing an outfit. If you’re feeling “hat-shy,” know that there is a hat out there for you: boater, wide brim, cloche, fedora. In straw they are the perfect tropical accessory. Plus they are so fun to pose with!

Secret Stylist’s Tip No. 4

Dare to be bold! Pick a bold, fun design element to inspire your wardrobe and then use it boldly but sparingly. Pops of pink, orange, and yellow in your outfits will look fresh and tropical. Feathers, sequins, or fringe are super fun to experiment with, yet can still be timeless. I love sequins at the beach! They look fun and unexpected but will not make your photos look outdated if used with discretion. 

DONTs – Not Recommended When Styling Hawaiian Family Portraits

> Too many patterns. Hawaii is famous for its Hawaiian shirts, dresses with tropical floral prints, and matched patterned family attire. Coordination is nice, but you can go overboard and end up looking more like an advertisement or worse like a hodgepodge of busy flower print. 

> Shoes are optional. If your session is at the beach, don’t wear shoes–no matter your level of formality. They’ll just get wet, sandy, and will sink into the ground.

At a different location, i.e. rocky outcrops, forest, jungle, shoes are optional and based on your overall look. Barefoot is always in style and looks beautiful! 

Large family walking on Maui beach without shoes

> Writing & brand names. It’s best to avoid slogans, brand names, or logos on wardrobe. Some children’s brands put rhymes or empowering slogans on kids’ shirts. For photos, I advise against that. They often become outdated and draw attention away from you or your child.

You’re not a billboard after all. You’ll be glad to have chosen something timeless. 

> Don’t overdo it with statement pieces or accessories. Two (max three) is good. Four can be too much. Pick two places to match in statement color or design element.

For instance, if your playful element is pompoms, pick two items such as the rim of a skirt for mom and a hat for your girlie. If your statement piece is raffia, maybe earrings for mom and a raffia hat for baby. Two items will guarantee that your family wardrobe will look tied together but not overdone or matchy-matchy.

What to wear to a family photo session – a fun colorful inspiration with pom pom accents

Secret Stylist’s Tip No. 5

Bra straps or slips can be a source of frustration. If you think you might have to fuss with them, bring a strapless bra or some nipple stickers just in case. I always carry safety pins and fashion tape. Another good item to have on hand is lip balm or lip gloss. Instant refresher for the face.

Secret Stylist’s Tip No. 6

No matter how body positive, everyone has some areas they’re conscious of. Yes, even or maybe especially models! So don’t worry know that you’re ready as you are–it’s the clothing that needs to step up and bring out your most attractive self.

Wrap skirts and dresses are flattering on mostly everyone, especially if they’re cut from a draping fabric. Skinny belts can be used to create a waistline.

After that it’s all posing! You can age someone by 10 years with the wrong lighting, or make them look 15 pounds heavier. Or you can do the opposite! Pick a skilled photographer with a good eye for detail, and who’ll direct you well.

How To Coordinate For Your Maui Family Portrait Without Being Matchy-Matchy?
A family wearing outfits with the same Hawaiian pattern that are too matchy

Here’s a fool-proof way to make your family look coordinated without looking like an advertisement or an perfectly matched set. You can use this trick for all kinds of occasions, not just photo shoots.

Step 1: Select a single patterned outfit for one person. Two people share the same pattern if you’re a large family (5+), or if you feel confident, you can find another similar pattern, maybe in a smaller print.

Step 2: Pick 3 or 4 colors from that pattern to dress that you like.

Step 3: Dress everyone else in those colors plus neutrals (beige, white, sand, gray).

Solids photograph well, and that one pattern is often enough to add some tropical pizzazz.

Short-cut: If you still feel overwhelmed, go monochrome! Just pick one color family, like blues and give each family member their own hue, aka specific dark or light sage of blue. That will eliminate all the pressure of matching colors.

Inspiration Boards For Styling Your Maui Family Beach Portrait

Here are some inspiration boards for different looks ranging from pastel romantic to bold sherbet tones.

Outfit inspiration for family photos on Maui – blue tones with tropical pattern and raffia accents
A family outfit inspiration guide for photos on Maui – pastel pink, yellow, and blue for a sunrise session
What to wear to you family photo session on Maui – a vintage lace outfit
black tropical modern outfit inspiration for a family beach photo session on Maui

For more inspiration for family wardrobe styling, check out the Emma Wyatt Pinterest!

Where to Shop for Your Maui Family Photo Session?

Here are some of my favorite brands for pulling wardrobe from for shoots. Over the years, I’ve found satisfied with the quality of these brands. Their clothing looks good in photographs and often they offer pieces with interesting cuts, patterns, and colors.

For Mom: J. Crew, Ted Baker, Kate Spade, Vintage finds from Etsy or TheRealReal, Calvin Klein, Ralph Lauren, Michael Kors, BHLDN, Tommy Bahama, Dolce & Gabbana, Rent The Runway, Norma Kamali

For Dad: J. Crew, Tommy Bahama, Levi’s, Perry Ellis, Mack Weldon, Nordstrom, Prada, Hugo Boss

For Kids and Babies: Coco Moon Hawaii, Feather4Arrow, Janie & Jack, Mini Boden, Old Navy, Tea Collection, Billabong, Roxy, Trish Scully, Dolce & Gabbana, Primary, Hope & Henry, Maisonette, Stella Cove, Etsy for vintage or one-of-kind pieces

Emma Wyatt Photography also has curated a Etsy Shopping list with vintage Hawaiiana items.

A Local Shopping Guide For Family Photo Session?

Perhaps you’re on island and discover that you’re missing an outfit for someone. I routinely leave someone’s clothes at home when I travel. Don’t worry!

There are some great places on Maui to shop for your photo session. In fact, these stylish kids’ and ladies’ boutiques will ensure that your tropical look is on point! I have a whole blog post dedicated to it.

Maui shopping guide the best boutiques for kids
Further Reading

––> 5 Tips for a Stress-free and Fun Maui Family Photo Session

––> Shopping on Island for Your Maui Photo Session

––> Budget friendly wardrobe styling for Maui Family Photo Session

––> Janie & Jack Shopping Guide – A Fool-proof Way to Dressing For Your Family Session

––> Hair Styling for Windy Beaches

What To Wear To Your Maui Family Portrait

Copyright © 2020 Emma Wyatt Photography. All rights reserved. 

Maui Family Photographer | Maui Babymoon Photographer | Maui Elopement Photographer