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Pumpkin Patch Photos (And what to wear for a fall photoshoot!)

Oct 5, 2021

Pumpkin Patch Photos

I have never really been one for “pumpkin patch” photos, but as they say, “once you have a baby”… suddenly you feel a distinct pull to dress her up in fall garb and surround her with pumpkins!?

So regardless of whether or not you have kids–with fall comes LOTS of opportunities for fall photos–whether they be family photos, engagement photos, just because photos–whatever! I get a lot of questions about what to wear for photoshoots, so I thought it was a good time to talk about some pointers (and share our photos of our pumpkin patch adventure!)

Pumpkin Patch Photos (And what to wear for a fall photoshoot!)

Last Friday, we took a trip to Jack’s Pumpkin Pop-Up in the city and met our friends Sam and Kelley (and Sam’s baby AKA June’s BFF Henry) for some old fashioned pumpkin patch fun. We weren’t sure what to expect, and it was an experience to say the least, but be told, we never would’ve made it out to the suburbs to take pumpkin patch photos, so I’m really glad this place exists!

If you live in the city, I think it’s a fun little fall activity to do regardless of whether or not you have kids! They have three bars (with a really good beer selection), a food stand with great looking food (although we didn’t eat there, so can’t confirm), fun carnival games and TONS, and I mean–endless Instagrammy photo opportunities. It would be fun to do with a group of friends, or even a date! If you live in Chicago and have been wanting to check it out, I will include some insider tips below.

If that doesn’t apply to you, feel free to skip ahead to the next section!

Jack’s Pumpkin Pop-up considerations: 

If you have kids: Get there right when they open at 4pm, because as time goes on it turns more into a bar-type atmosphere and gets increasingly crowded. Also, the music is loud! In hindsight we wish we would’ve had noise cancelling headphones for June.

If you don’t have kids: You’ll probably prefer arriving a little later once the kids have gone home 😛 Unless, that is, photos are your main priority–then you’ll want to get there at 4pm as well, because there’s hardly anyone there and it’ll be the best lighting for your photo shoot!

Heads up on admission: It is NOT cheap. $25 per adult. WHEW! But, that does include photography, which is a great bonus. Just make sure to flag down the photographers so you can get your money’s worth!

It’s ON Goose Island, not AT Goose Island! I pulled a typical Jess move and thought this place was AT Goose Island (as in the brewery) but turns out its ON Goose Island As in, the geographic location between Bucktown and Lincoln Park. (It’s not a real island, it’s just surrounded by off-shoots of the river so is *technically* surrounded by water.) Neal was not thrilled with my oversight as June was screaming in the back–whoops!!

Anyway, that all being said, it was a really fun little outing and I’m glad we went. I die every time I look at these photos. HER LITTLE JUMPER!! I got a lot of requests to share outfit links as well some some fall photo outfit inspo, so keep scrolling if you’re interested!

Pumpkin Patch Baby Photos

What to wear to pumpkin patch

Tips for planning fall photo shoot outfits: 

Before we get into what we’re wearing here, some overall tips on planning your fall photo shoot outfits (and any photo shoot outfits in general!)

Pick the “star of the show” outfit first and plan everything else around that: 

I would say YOUR outfit or kids/baby outfit is the best to start out with. Whatever you’re most excited about OR the hardest thing for you to shop for. (For what it’s worth, this applies to any kind of photo shoot–I would say the same for engagement photos too–pick your outfit first, then choose his outfit, etc!)

So in this instance, I started with June’s outfit, because that’s what I was most excited about (and also she had the most limited options because every piece of fall/winter clothing I had purchased for her is still too big!) then I picked my outfit, and I told Neal to put on something that didn’t clash.

That leads us to the next point…

Wear complimentary colors, but you don’t have to match! 

You all know I’m big on color schemes when it comes to packing for a trip. The same applies to photo shoots!

I think it’s helpful to pick a color scheme for a photo shoot–I don’t think it’s necessary to all “match.” Whatever you’re wearing should compliment each other, but it doesn’t necessarily all have to be the same colors!

If you notice, Neal isn’t wearing the same colors as June and me, but we still all go together. He’s wearing navy and white. We’re wearing orangey-browns and white. White is the common thread! Neal and I are also both wearing white sneakers that helps the cohesiveness–both from a color and from a style standpoint.

In the fall, I tend to gravitate toward neutrals, which makes it easy to mix and match.  I love browns, burnt orange, black, dark navy, white, cream, etc! (They’re a lot easier to coordinate than bright colors!)

What about patterns? 

I know the age-old “photo clothing” rule says to stay away from patterns, but I disagree! Just as discussed above, I think if you want to wear patterns, they should compliment one another, and not clash.

For example, I think if your whole family wanted to wear plaid–that would be VERY overwhelming. But if one person wore, say, a buffalo plaid, another wore thin black and white stripes, and another wore subtle polka dots, I think that’s totally fine and makes for an interesting outfit mix that feels very organic and not too “staged.”

Tip for pattern mixing: Vary the scale of your patterns. You’ll notice that my stripes are the largest pattern but the coloring makes them subtle. (If they were SUPER bold, thick black and white stripes, that would be too much and too out of balance–know what I mean?) Neal’s shirt is a very small, busier pattern, and June’s bow has a very small, but very subtle gingham pattern. The reason these all work together is that the scale and colors are varied and there isn’t ONE pattern that is super loud and dominant.

Don’t forget about the details! 

I think often what makes an outfit are the details. In this case, it’s the scarf in my hair, and June’s knee socks! Don’t forget about the details 😉

Consider your background/setting: 

Where will you be taking photos? If we’re talking about pumpkin patch photos, you’ll want to choose things that go well with pumpkins! (AKA–not bright orange.) Earth tones, muted hues, and darker colors like black and navy will be a great bet. If you’re taking photos in say, a corn maze, try and wear tones that are darker (not beige, for example) so you don’t blend in.

Don’t feel like you have to buy anything new! 

I know it’s fun to shop for an occasion like a photoshoot, but don’t feel like you have to buy anything new! In fact, I love wearing things I already own and love (and wear often) because then I can look back and say, “OH I remember I loved that skirt!” and it’s a true representation of our lives at that point in time!

babies in pumpkin cart

Above: June and her bestie Henry! 

June’s outfit details: 

Jumper: She’s wearing this little jumper from Old Navy!

Onesie: Her little ruffle onesie underneath is a hand-me-down, but this one is very similar!

Bows and socks: Her gingham bow is part of this four-pack from Amazon. I love these ones because they fit her before all other bows were too big, but they’re super stretchy so she’ll wear them for a long time! Truthfully I forget where her knee socks are from, but these are super similar!

Henry’s Outfit Details:

Overalls: OshKosh (Baby Gap also makes super cute ones!)

Chambray baby hat: Similar here from Old Navy 

Tee: Similar here from H&M! 

More baby fall outfit ideas: 

baby fall outfit ideas | Pumpkin Patch Photos

What I’m wearing:

Almost everything I’m wearing here is years old! But I will link similar below!

Skirt: Similar here from J.Crew factory (and on sale!) I also just got this adorable corduroy jumper for Paris (I got it in black but they have tons of colors) It would also be so cute for fall photos!

Tee: Similar here. Would also be cute with different colored stripes! In my case, I’d probably do navy and white stripes here to go nicely with Neal’s navy.

Shoes: My tried and true https://bit.ly/3kq7psYFreda Salvador sneakers. Reviewed here along with my other favorite white sneaks!

Hair scarf: Old scarf–most of mine are either thrifted or bought at markets on my trips (I love scarves as souvenirs!) Highly recommend checking your local vintage shop! See this post on how to tie a hair scarf.

More women’s fall outfit ideas: 

I also love the idea of wearing a flowy dress, or a jumpsuit, or cute overalls! There is no right or wrong thing to wear–you should wear what feels most like “you!”

men's fall outfit ideas

What Neal’s wearing:

Neal is also wearing items that are a couple years old, but similar below!

Short sleeve button down: Bonobos–I know, shocker. He owns half the store. It’s his favorite go-to brand for both fun stylish shirts and great basics. Will link more Bonobos shirts below!

Shorts: Bird dogs. Super comfortable with built-in underwear! They feel like gym shorts but are constructed to look like everyday shorts. (He also loves the shorter length!) Bonobos shorts are another favorite of his if you’re looking for something a little more polished.

Sneakers: Converse! Classics that never go out of style. He also has owned and loved Jack Purcells as well which are a similar look!

More men’s fall outfit ideas: 

Pumpkin Patch Photos Pumpkin Patch Photos with baby Baby at Pumpkin patch Family fall outfits

Fall family activities

Hope this was helpful! Happing fall-ing!

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