Issue 81: Summer style, third-trimester
A summer style guide from photographer Gillian Stippa
One of the most fun things we get to do here is ask cool moms how they get dressed and then share their outfits with you all. This week, Hudson Valley-based photographer Gillian Stippa is showing us how she navigates style in the third trimester (hint: an enviable vintage collection and inspiration from Copenhagen). Welcome, Gillian!
I’m a photographer, a Coxsackie native, and as of writing this, extremely pregnant with my second child while chasing a two-year old named Trip around a house that also contains my husband, two dogs, and the general energy of a place where no one is fully in control. The dogs: Pip, a chorkie the size of a large potato who is somehow 12 years old and completely unbothered by this fact, and Richard, a German Wirehaired Pointer built like a wide receiver who acts like he too is the size of a potato. My husband is also in the mix - a sports-loving, hat-making, neat-freak big softy who weirdly drinks milk with every meal.
I left Coxsackie for New York City, then spent a year living in a van with my husband driving around the country, which sounds romantic and mostly was, except for the part where you are living in a van. We happened upon Boulder, Colorado during our travels and thought it’d be a pretty nice place to live for a bit — a bit ended up being six years. I’m not sure if it’s the Hudson Valley specifically or everything that happens to be in it that brought me back: my siblings and parents, soft serve ice cream, goats, city people to make fun of, or the old oak tree in the backyard we climbed as kids.
I’ve been shooting food for 12 years and I’m done with it, basically. Not done-done, but I’m pivoting hard toward portrait work, because photographing people is scarier and therefore more rewarding. I went to film school, have run some marathons, genuinely love being outside, and am also someone who could watch six consecutive hours of Summer House without blinking. Maybe I’m the potato. These are not contradictions.
On the style front: after college I took over my uncle Steve’s vintage clothing business, a collection - hoard, really - he’d been building and selling since the 1970s. So I grew up around old, smelly clothes. My style is eclectic in the way that happens when you’re a millennial that listened to punk rock in middle school, Bon Iver in high school, embarrassing EDM in college, and is now forced to listen to Steely Dan and Miss Rachel. Boulder gave me running shoes, New York gave me costume, and the van year gave me a very high tolerance for rewearing the same thing.
Pregnancy, round two, has given me a completely different relationship to getting dressed. Not worse necessarily (although a little) - just more focused. You figure out fast what you actually like versus what you were wearing out of habit or aspiration or some vague idea of who you were trying to be. I’m not trying to be anyone in particular right now. I’m trying to find loose linen and 90s crop tops. It’s clarifying, actually.
Everything here except the shoes is from Steve’s. The jersey is red with yellow and navy stripes, worn over a white collar, paired with camo pants, because that is a thing you can do. I like color, but I like it better when it’s next to something that has no business being next to it. Camo is very serious. A red hockey jersey is not. Trip, for his part, is also very unserious.
Copenhagen, six months pregnant, wearing this outfit more than once because why wouldn’t you. Copenhagen is the dream city, I would live there if I could. I thought about leaving my husband for a Dane while I was there, but reconsidered when I remembered I had a child and was pregnant.
This blazer goes with everything. I have tested this theory extensively and it holds. It’s the kind of vintage find that makes you feel like the whole endeavor of thrifting is worth it — oversized glen plaid, deep pockets, no notes. Trip is in Converse, which are extremely cute and extremely annoying to tie, and that about sums up parenting in general.
The clogs are handmade from Copenhagen, which feels appropriate given my feelings about Copenhagen. Red, because I will always choose red shoes if red shoes are an option. The pants are thrifted of course - yellow and olive stripe, wide leg, the kind of thing that looks chaotic on the hanger and correct on an orangutan. The top is feminine and the pants are not and that’s the whole idea. It works especially well when you are nine-months pregnant and the goal is to remain a person who got dressed on purpose. The belly is out because there is no other option at this point.
Red socks, stretchy skirt, Gucci loafers I found on eBay because I have standards but am also cheap. The tank is worth mentioning - wide collarbone-skimming opening, broad straps that hit almost at the shoulder’s edge, sleeveless. It has a very 1960s, French Riviera thing going on that I am completely susceptible to. I bought it in multiple colors in Copenhagen, which tells you everything you need to know about how I shop when left unsupervised. Richard - the dog, my first son - was kind enough to position himself as a footrest for this photo, which is the most useful he has ever been indoors.
This is what summer looks like. I think I slept in the shorts too. I will be wearing some version of this every day until further notice, which I feel my family should be warned about. I am not a heat person under normal circumstances. Adding third trimester to a summer in the Hudson Valley is a choice I made nine months ago and am now fully reckoning with.
One For Us
In this section, we’ll share what we’re enjoying for ourselves these days.
[Gillian] - My younger brother is currently living a deeply enviable life - traveling, meeting strangers, exercising, being single, existing in the world without a diaper bag. He sends me texts from all the girls that are harassing him. I send him videos of Trip drinking the dog water. In the absence of having the bandwidth to actually enjoy anything myself at the moment (other than Summer House and an exorbitant amount of kiwis), I have found that enjoying someone else’s life works almost as well. Highly recommend finding a person in your orbit who is out there living and attaching yourself to their experience like a barnacle. It’s free and requires very little of you.
[Ashley] - I know a lot of people in these parts have installed drip systems in their garden beds for obvious reasons. I considered installing one this year but realized how much I love going outside before my child wakes with my coffee in hand to give all of my plants a good, long drink in silence. My nervous system sighs a big ‘ol thank you and I can’t deny her that.
[Maddie] - When I was nine years old, I presented the case to my parents that I should be able to watch Ever After in theaters despite its PG-13 rating. I eventually won them over, and now, decades later, I still appreciate a Cinderella retelling. Lady Tremaine, the classic story told from the perspective of the scrappy, resourceful stepmother, is my book of the summer. Appropriately enough, my mom is also enjoying it.
One For Them
In this section, we’ll share what’s making parenting small children more enjoyable these days.
[Gillian] - Family that shows up - actual humans who live nearby, love your kid, and will come over on a Tuesday without the need for dollars. Does it come with strings though? Yes. Strings are the price of admission. But in a world where childcare costs one million dollars an hour and daycare waitlists begin before the child is even born, having people around who will take Trip for an afternoon is the greatest logistical gift I have ever received.
[Ashley] - In our household, we absolutely bribe and reward to convince our daughter to do the things we want her to do. Somehow she and my husband came up with the term “meh meh” for dessert. “Meh meh” is our most convincing item. Our go-to are the ever delicious Kolsvart swedish fish. If she clears her plate after dinner, one fish. If she clears it without us asking, two fish. Red fish, blue fish (couldn’t resist).
[Genevieve] - The thing making my daughter feel like the Queen of Summer this week: Ring-Pop Style Ice Pops. Two factors that make these a life-saver for me: 1. choose silicone molds over plastic if you have the patience of a mule like me, and 2. make the pops out of smoothie, yogurt + fruit, etc. and you can be the chill parent who says “yes” when they ask for an ice pop for breakfast.
[Maddie] - When my daughter grew out of her pasta pants, I went back to the well at Petit Pilou, only to find this charming dress. Perfect for a gal living in an area with egg stands galore.
In the Neighborhood
We live in the Mid-Hudson Valley and we’re keeping tabs on these (mostly family-friendly) events near us. If there’s another event you’d like us to share, please send it our way!
Summer Events
Thursday, June 11 to Saturday, June 13 - Circa Eternity at Lumberyard, Catskill
Friday, June 12 - Read with Ewe and Me, Staatsburg
Friday, June 12 - Karaoke Fundraiser for Germantown schools, Germantown
Friday, June 12 - Reading and Kids’ Poetry Workshop with Anna Vitale and Flexible Letters Workshop, Tivoli
Friday, June 12 - Remember You Mama’s Circle, Kingston ^
Saturday, June 13 - Paint Making with Invasive Plants Workshop, Hudson
Saturday, June 13 - Mermaid Parade and Reading with Jessica Love, Tivoli
Saturday, June 13 - Big Pride Hoedown, Hillsdale 🏳️🌈
Saturday, June 13 - Planting The Seed with Cesar, Newburgh
Saturday, June 13 - Flag Day Parade, Hudson
Saturday, June 13 - Catskill Pride Festival, Catskill 🏳️🌈
Saturday, June 13 - Fermentation Festival, New Paltz
Saturday, June 13 - Clothing Swap at Good Work Institute, Kingston
Saturday, June 13 - Kinderhook Street Tag Sale, Chatham
Sunday, June 14 - Woodstock Pride Parade, Woodstock 🏳️🌈
Sunday, June 14 - Tour de Red Hook, Red Hook
Monday, June 15 - Luncheonette Free Community Meal at Pocketbook, Hudson
Tuesday, June 16 - Summer Storytime with Mr. Purple, Hudson
Thursday, June 18 to Sunday, June 21 - PS21 Groundtone Music Festival, Chatham
Friday, June 19 - Cooking Class at Stissing House, Pine Plains ^
Friday, June 19 to Sunday, June 21 - Future Sound Of Nature Weekender Festival, Red Hook
Saturday, June 20 - OutHudson Pride Parade, Hudson 🏳️🌈
Saturday, June 20 - Summer Solstice Carnival at Spiral House Park, Saugerties
Sunday, June 21 - Goat on a Boat puppet show at Quinnie’s, Hudson
Starting June 25 - Italian Tots & Tales, New Paltz
Saturday, June 27 - Shaker Museum Afterparty: The Shakedown, Chatham * ^
Sunday, June 28 - Pride 2026 Fun Run 5K, Poughkeepsie 🏳️🌈
Saturday, July 4 - Fam Jam, Saugerties
Starting July 7 - Catskill Mountain Music Together classes, various locations
Tuesday, July 7 - Annual Summer Party at Hudson Area Library, Hudson
Saturday, July 11 to Sunday, July 12 - Tanabata Festival at Dassai Blue, Hyde Park
Saturday, July 18 - Chatham SummerFest, Chatham
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Ongoing Events
Mondays - Songs & Stories at Ulster Public Library, Ulster
Mondays - Family Resource Center Playgroup, Valatie
Mondays - Tunes and Tales at the Red Hook Library, Red Hook
Mondays - Move + Nourish prenatal movement workshop at At Play, Rhinebeck
4th Mondays - La Leche League meetings, Chatham
Mondays and Tuesdays - Toddler Jams, Germantown
Tuesdays - Storytime with Robbie at Starr Library, Rhinebeck
Tuesdays - Family Resource Center Playgroup, Hudson
Tuesdays - Preschool Story Hour at Claverack Free Library, Claverack
Tuesdays - Tiny Tots at Palenville Library, Palenville
Wednesdays - Runs with Return Run Club, Hudson
Wednesdays - Family Resource Center Playgroup, Valatie
Wednesdays - Dancing Connections and Baby Dance Club at Full Circle, Gardiner
Wednesdays - Music & Movement at Starr Library, Rhinebeck
2nd Wednesdays - La Leche League meetings, Hudson
Thursdays - Music & Movement Storytime at the Hudson Area Library, Hudson
Thursdays - Family Storytime at Kinderhook Memorial Library, Kinderhook
Thursdays - Family Resource Center Playgroup, Hudson
Thursdays - Wiggles & Words at the Red Hook Library, Red Hook
Thursdays - Adult Art Club at Super Stories, Kinderhook
Thursdays - Baby & Me at Claverack Free Library, Claverack
Thursdays - Baby and Toddler Playgroup at D.R. Evarts Library, Athens
Fridays - Tunes and Tales at the Red Hook Library, Red Hook
Fridays - Family Play and Hang at Starr Library, Rhinebeck
Fridays - Art Focus Fridays at Kinderhook Memorial Library, Kinderhook
Fridays - Music & Movement at Claverack Free Library, Claverack
Fridays - Story Time at Catskill Public Library, Catskill
Saturdays - Hudson Farmers’ Market (back outside!), Hudson
Saturdays - Art Workshop at Art Omi, Ghent
Saturdays - Art Nest at Wassaic Project, Wassaic
Saturdays - Bodie’s Lighthouse Lab at D.R. Evarts Library, Athens
Saturdays - Catskill Mountain Railroad train rides, Kingston
Saturdays - Free Maker Sessions at Super Stories, Kinderhook
Sundays - Community Group Run at Neighbor Running, Hudson
Sundays - Art Projects: Youth Painting & Drawing Classes (ages 4+) at Cone Zero, Catskill
^ = for adults
* = will likely sell out, so book soon
🏳️🌈= family-friendly Pride events!