Picture this. It’s a few weeks before your scheduled spring family photography session and you’re starting to plan out some outfits. You have your dress picked out, maybe a nice pair of pants and a button up for Dad, a dress for your school aged daughter, but you keep coming back to the question “what does my toddler wear?” So often, we fill toddler closets with practical clothes that will get ripped and dirty that it’s hard to find a good outfit that is comfortable and also a little on the more dressy side. I get it! This post is here to help you figure out how to dress a toddler for family photos.

I’ve always found dress my toddler boy more challenging than my daughter. Once they’re walking, throw a cute dress on a little girl or a frilly romper and you’ve got a win – especially for the spring and summer months. Little boys, however, tend to own an abundance of sweatpants and graphic tees – neither of which are ideal for family photos.

If you’re struggling to find a great dress that looks good with the outfits you’ve picked out for everyone else, feel free to check out this post to find my guidelines on how to choose cohesive family outfits!

When thinking of how to dress your toddler for family photos, consider everyone else’s outfits. Obviously we want to match colours and not have too many patterns present amongst the family, but you always want to match the style. If you’re in a gown and Dad’s in his suit, a toddler in jeans and a sweater will look a little off. In this case, I’d recommend finding him some little slacks and a nice button up like daddy! But if you’re wearing a mid-length sun dress and dad is in some khakis and a light sweater, then this look can work great!

Check out a family session with a toddler boy here!

Here are some of my favourite looks for a toddler boy:

1. Cute overalls over a nice henley shirt.

I’m not talking about the OshKosh denim overalls here. While those can look super cute, they are inherently casual and wouldn’t be something I’d personally select for my sons. A pair of nice linen or cotton harem overalls gives the look a little more class. My personal favourite pair (which we own multiple pairs of) are Tate & Adele’s Brody Romper. These are handmade in the USA, so if you’re thinking of grabbing a pair for your family photos, make sure you have enough time to order. She also has an adorable henley top option that pairs well!

2.Linen suspender pants over a nice shirt or sweater

A pair of adorable suspender pants always makes little boys look classy! Once again, Tate & Adele’s are my favourite, but you can also find them all over Etsy and even at H&M or the Gap sometimes!

3. Suspenders and jeans

If you’re going for a slightly more casual look, but don’t want just jeans, add a nice sweater or a cute top and throw some suspenders over them! Suspenders are a great and easy way to dress up jeans a little bit, and they also just look so cute on little boys!

4.Cute grandpa cardigan with some khakis or chinos.

Little boys in Grandpa cardigans are my favourite! Elbow patches, big buttons. Throw them over anything and they look adorable! This is our other go-to, especially during early spring when there’s a bit of a chill in the air. Wear it with khakis or chinos for an adorable dressed-up look!

If you’re still unsure and are thinking “I just wish there was someone who could help me with this!” and you’re in the Vancouver area, I’ve got you! I help all my clients style their family and choose their outfits for our sessions. It’s just another service I offer as part of your family photography experience to ensure that your session in stress-free and that you’re obsessed with your images!

Enjoy this post? Check out similar ones:

• 5 Reasons Spring is the best time for Family Photos
• Why your Family Photos Deserve to be Printed
• North Vancouver Photographer: Family Session