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12 Cute, Comfy Easy-To-Wear Spring Break Outfits

I have a “family vacation” philosophy that I’d love to share if you are into random internet people telling you what to do with your lives and how to raise your kids (…most people LOVE THAT). I learned this the hard way: When your kids are infants (under one), go wherever you want because they are mostly mobile and they don’t care/know what is happening. When your kids are toddlers (5 and younger), lower all expectations down to ZERO, get in your car, rent a house near any sort of body of water (crucial ingredient) with another family of similar-aged kids whose parents you enjoy enough to commiserate with and just chill (camping with another family is PERFECT). Do whatever you can to not have to get in a car to start your day, avoid hotel rooms so you don’t get stuck in a “nap trap” sitting in the dark, avoid nice restaurants because toddlers know how to ruin your good time and hell, even avoid going to a city where you want to experience “culture” because you might not actually get to enjoy much of it. I’m sure a million of you will balk at this because I’m sure many of you loved your city + toddler experience. But when we went to Australia FOR THREE WEEKS for Brian’s work, the kids were 3 months and 2 years old. We barely left the house due to nap trap, they ruined every martini we tried to get at our 5 pm dinners and came home saying it was mostly a waste of a lot of money. Same thing when we went for 2 weeks to New York for work around that same time (we went for my work). We were so exhausted and drained and everything was on their terms. Save your $$$. The toddler years require too much work and they are too unpredictable.

Now, when they become school-aged and you want a “vacation” (different than traveling) meet them where they are at and hone in on your shared interests. For us right now, it’s nature, somewhere with water and sun, a sense of adventure, few crowds, and somewhere that avoids screentime for all of us. But for now, our whole family is very happy when we are outside (swimming, zip lining, snorkeling, hiking, animals, horses, farm visits, sitting by a lake and reading, more swimming, etc). Ideally somewhere with delicious food too.

Furthermore… (Yes, I’m still blabbing about my philosophy, I’m a Virgo y’all and an Enneagram 7 so I like to seriously plan my fun). I plan every day the same – the first half of the day is super active (moving our bodies somehow) and the second half of the day is inactive (reading, chilling, reading, sipping on something while kids swim). Last year we were able to go to Costa Rica (far exceeded our super high expectations) and this year we are headed to Kauai (never been so excited). I planned our entire itinerary, including activities, in JULY, like a real mom-boss/psychopath (I’m very grateful to be able to do this with our kids).

But last year I crapped the bed on my Costa Rica wardrobe. I was fine for our rainforest mountain hiking/ziplining days but didn’t bring the right lightweight clothes for the super humid and hot beach time. I felt very sticky/hot in my denim shorts at night. This year I’m planning a bit more (as you will see), and while I’m not bringing all of this (and returning some because I simply don’t need this many clothes) I wanted to show you what I found out there that I’m really loving right now (and per usual I kissed a lot of toads).

If you notice a change of scenery in the photos, no it’s not another out-building at the farmhouse! It’s our friend/photographer Kaitlin Green’s new studio space! She, Gretchen and I had so much fun shooting these looks in her new space.

My Hands Down Favorite Caftan

Hat | Coverup | Swimsuit | Bracelet (similarish) | Platform Sandals | Inner Tube

This is the most lightweight, easy breezy cotton (but nice quality) caftan out there. I used to own the same one in blue but longer and loved it. The alternating stripes create a pattern that moves your eye around and thus distracts from what is underneath. You don’t have to tie it either if you want it to be loose (the tie is on the inside). It also comes in other colors (the darker colors aren’t see-through and you can wear it as a dress), but my goodness it’s PERFECT. I feel so cute, comfortable, and not too exposed to belly up to a restaurant at the beach or hotel.

A Shirtdress That Actually Has Shape (And So Affordable!!)

Headband | Sunglasses | Dress | Purse | Bracelet (similarish) | Sandals

This dress is the real winner of the season. It’s from Target and while I love the idea of Target clothes I do find that sometimes their cuts aren’t great on me or the fabric is just meh. This is lightweight (looks heavier than it is), has a seersucker vibe that lends itself to being casual, doesn’t need to be steamed, and has that cute gathering detail at the front but nothing on the back so it gives you a sense of the waist with extreme waist comfort!!!!! Might be too warm for extreme humidity, but it’s absolutely coming with me for nighttime casual dinners. I’m so comfortable and I feel really cute (add a trendy bag to take it down a notch in the mom category).

A Really Good Lightweight Short-Sleeved Blouse

Hat | Purse | Blouse (similar) | Shorts (similar) | Sandals

I feel like I’m not really selling this shirt well enough here, but I’ve had it for years and wear it frequently every summer because of how dang lightweight, comfortable, and wrinkle-resistant it is (or I should say it looks good with slight wrinkles and holds it shape). Emerson Fry makes new ones every year in the same shape/fabric but different colors. HIGHLY RECOMMEND. Big old armpits, cute bell sleeves, thin high-quality cotton. Just glorious. Shorts are from last year (yes, we should have steamed them but they were the last outfit and I was literally out of steam). Comfortable and certainly practical/easy to wear. And while I don’t love that Target has so successfully knocked off Claire V, if Claire isn’t within your budget this bag is so cute (if you have the budget buy from the original designer, IMHO. They just came out with a new color of the grande fanny that the entire EHD team is swooning over). Tevas, always FTW – water shoes for rafting through the canals 🙂 Also yes, that is a new WONDERFUL hat and stays on with the tie situation. It’s the best hat on the market if you ask me.

A Trendy Linen Set

Sunglasses | Top + Shorts | Purse | Bracelet (similarish) | Sandals

Here is one I bought to show you that isn’t really me, but it is pretty dang good if this is your style… and from Target!!! I’m more of a denim shorts/blouse combo lady, but this linen set from Target is legit very good and my team of Gen Zers (and millennials) LOVE it. I know this is very in and trendy but it’s hard for me not to see them as a pajama set or a dorky dad set (which I know is in, I read the news and “Kramer chic” is everywhere but it’s not for me). The purse helps LOL. If you are into looking fashion forward, like a cool dorky dad, and being really comfortable, this is a great set.

My New Favorite Flowy White Blouse

Hat | Sunglasses | Blouse | Swimsuit Top | Shorts | Bag (similar) | Heels

Now THIS is way more me. Last year’s jean shorts + a new flowy, easy breezy blouse (it’s fairly cropped, too, so you don’t even have to tuck), straw hat, and DONE. I wore it with heels here (which I’m still debating if I should even bring to Hawaii, but they are so cute, comfortable (for being heels), and make my legs look so long!!). Look how trendy I am with my silver bag 🙂 And way to go Target for that excellent hat. I’m only bringing one hat on our trip because I learned my lesson that wearing 2-3 hats at the airport and on the plane will get you a lot of weird looks and could possibly embarrass your husband and children, especially when people recognize you from social media and perhaps assume correctly that you are weird).

An Incredibly Good Swimsuit Coverup Pant

Hat | Swimswuit | Pants | Bracelet (similarish) | Platform Sandals

100% bringing and wearing this outfit. If you haven’t dabbled in compression suits yet but have been curious, might I introduce you to Stylest (TA3 is also excellent and I love Andie and Summersalt too). This one is obviously more of a rash guard which is great for me because I get really bad sun rash if I’m not really protected (and no I don’t tan because any “tan” would just be a burn anyway). I feel extremely good in this due to the shaping compression. I first bought it in the rainbow pattern (which I call my toddler suit). It’s not exactly what I think most men fantasize about, but I feel great in it which is far more important and it’s great for family vacations. These Target pants are AWESOME (those are an XS so def size down). The suit has shelf support, BTW, but you can buy swim bras for underneath which looks like a cute bandeau for extra support. I LOVE this look. The hat has a sweet leather trim detail and the shoes are awesome for the price (I refuse to spend big money on any espadrilles as they never last more than a season for me).

The Perfectly Draping Caftan

Hat | Sunglasses | Coverup | Bracelet (similarish) | Sandals

This caftan might not look that incredible but the fit and fabric are AWESOME. It drapes so beautifully. Despite being so voluminous, even with my big buoys, it lays flattish on the stomach. I wish it came in a million colors – I’d buy this caftan many times over. The fabric is thin and silky but not clingy (I’m not sure how breathable it is, it’s likely a synthetic mix). Maybe it’s the black with a vertical striped floral pattern that makes it so flattering??? Dunno. And if you don’t own Haviannas flip flops get yourself a pair (I like Tkees for nicer ones but they were all sold out). They last forever, come in a million colors, and are strangely comfortable.

A Cute Oversized Cover-Up

Hat | Button-Up | Swimsuit Top | Shorts | Sandals

I’m really into menswear button-ups as cover-ups but the long sleeve ones can be too hot. Kaitlin and Gretchen convinced me to wear this bikini top underneath but I’m projecting extreme discomfort in it (it’s actually a swim bra that I ordered to go underneath the blue/white striped one piece so that you can unzip it and have a cute swim bandeau showing). The oversized blouse is a pretty cute coverup which I plan to bring and those pull-on shorts were Madewell’s like #1 short last year for good reason. Please ignore the bunion, per usual. May I distract you with the best hat ever (again)!

Wait, Is That A Swim Dress?

Button Down Shirt (similar) | Hat | Swim Dress | Bracelet (similarish) | Sandals

Yep. With Pockets! Another one from TA3 (I’m currently manifesting a patterned collaboration, BTW). It’s corsetted in the back, highly shaping, and definitely more resort wear than swimming, but I LOVE IT SO MUCH. Y’all, I can totally get in with the kids, dry off, go to the bar, grab a drink, and feel cute the whole time!! The sandals are my go-to from last year (still in excellent condition) and still available.

Another Cool “Kramer Chic” Set

Towel | Sunglasses | Button-Up Top + Shorts | Swimsuit | Bracelet (similarish) | Slides

Another set that I know is cute and trendy but I think I’m just too old to not feel dorky in it (I know that this is part of why it’s “cool” because dorky is “in” but some of us just aren’t buying in). But I’m showing it off because my team loves it and thought you might. Now this set (from Topshop) is really thick, so if you are going somewhere super humid this night not be right for you. I love those Nike slides, by the way.

A VERY Comfortable Dress

Dress | Bracelet (similarish) | Purse | Heels

Ok, this dress is soooooo comfortable, drapes really well, and I love that scoop neck. I personally think my “love pillows” are too big for the dress and it does make me feel like I’m hiding a baby in there, so I think it’s better on people will smaller boobs (so it hangs closer on the body). If it were cheaper I’d keep it because it’s so comfortable and still pretty. But if you are tall and smaller up top I really recommend this dress.

Obviously, My Vibe From Head To Toe

Hat | Blouse | Shorts (similar) | Sunglasses | Bracelet (similarish) | Sandals

While denim shorts aren’t exactly great in the humidity, this whole look from head to toe is just very me, and I feel so comfortable and cute in it. Oversized (and rolled) denim shorts, a new blouse that I can’t stop wearing (has a matching long skirt, too), classic birks (oversized brass buckle), and my favorite new hat with the toggle. The shirt is cotton, breathable, and the pattern and ruffles are so fun and playful.

A huge shout out to our wonderful photographer and friend, Kaitlin Green, who opened a photo studio with Paige Jones and it’s such a wonderful place to shoot. If you’re in Portland and need a photo studio for an event or for a photo shoot, I highly recommend this studio with these two lovely ladies running it.

Hope this was helpful for anyone needing some spring break fashion inspo! xx

*Photos by Kaitlin Green at Sunroom Studio

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1 month ago

Have a fantastic trip! I love Kauai!

1 month ago

You look so happy and confident in all of these outfits. Love all of the clothes. By far, my favorite fashion post that you’ve done, largely based on how joyful you appear.

1 month ago

I love all these looks! I am dying to know where the pink and red dress from the Instagram reel is from! 🧐 you have such great style Emily!

1 month ago
Reply to  Andrea

It’s the Palmerston Dress in Red Fil Coupe from Tuckernuck.

1 month ago
Reply to  Andrea

And that is the On Holiday Bag by Scout in French Blue Check from Riley Reigh Mod Market.

1 month ago

Emily I don’t know how you do it but you’re more fabulous every year! Love it all!

1 month ago

Ooh that swim dress! It looks fantastic. I think I would wear that just in general but that’s such a great option. Thanks for doing the work of trying all this stuff on. So many stores have closed where I live and ordering and returning clothes is so annoying so I’m thrilled some of these are just target finds.

Elizabeth Sims
1 month ago

Ok the swim dress is hot!! And I love your big smile in your favorite outfit : ).
I’ve been planning for Cost Rica, and a few other brands I’ve bought from are Buck Mason (the perfect tanks), Rowan California (the most elevated cotton shorts) , and Bearded Goat (chic sporty nylon shorts). For swimwear, Left on Friday has the long-torso styles I need. I got a long-brim bucket hat from Lack of Color that I am telling myself is cool even though I feel too old for it (but it’s so packable and has serious sun protection!) For a few nicer items, I went with DISSH.
This was such a fun, spot-on post!
P.S. I grew up at the beach in SoCal, and Rainbow makes the ONLY flip-flips, as far as I’m concerned : ). They go anywhere and last for years.

1 month ago
Reply to  Elizabeth Sims

Thanks for these recs!

1 month ago

So cute! Have a great time!!

1 month ago

Dying to know the fabulous location where these pics were taken. Looks like your rolling racks from your farmhouse closet, original iron windows but new baseboards and maybe drywall and concrete. Is this somewhere at the farmhouse?

1 month ago
Reply to  Bria

This was shot at Kaitlin’s new Sunroom Studio in Portland.

1 month ago

Emily, this post is so, SO helpful! I love the outfits and you’ve saved me for spring. Also, is there any chance you would post Costa Rica and Kauai itineraries with kids? I would LOVE, LOVE to see them and to get your recs.

1 month ago

Oh my goodness you will love Kauai! We’ve taken our five kids since there were four of them (ages 18 months!- 9) and more recently (3-13). I swear all you need are swimsuits with simple cover up /workout gear bc it’s a very casual vibe (I guess maybe depending on where you are staying) and more adventurous. My kids go from pjs to swimsuits, wash, and repeat. I hope you’ll do a post about your trip bc it will be fun to see where you explore! I will say we haven’t found many restaurants etc that we feel the need to go back to each visit, but we’re not going there for the food 😉

1 month ago
Reply to  Jenna

I was just coming here to say the same thing; I just got back from two weeks on Kauai yester, and I’ve been going there for decades. Kauai is not like the other islands, it is VERY, very low key. You’re going to be overdressed in “outfits.”

Places to eat:
Japanese Grandma’s in Hanapepe
Kiawe Roots
Lawai Market (just down from Warehouse 3540) – sandwiches and smoothies
Little Fish – breakfast and lunch on the road in Poipu (bagel sandwiches, smoothies, some bowls)
Kauai Poké Co. – they moved their fantastic food truck into a standalone space a couple years ago to the golf course next to the Hyatt. Don’t eat there, get takeout Plantation Bowls and walk down to the beach to eat.
Hapa Ramen
Kickshaw’s food truck
Lappert’s ice cream
Everyone goes to Da Crack (it’s fine, not reinventing the wheel); Koloa Pizza is good; Break+Feast is new and good (same folks as Kiawe Roots).
The farmer’s market that’s in The Shops at Kukuiula on Wednesdays is really good, you need to get there 10 minutes before it opens. Great produce.

1 month ago
Reply to  Jenna

I second this about the food, especially resort restaurants. But omg The Fish Express is my ride or die. It’s very close to the airport, and is always my first and last stop in Kauai.
I also agree that unless you’re on property at Princeville, the vibe is extremely casual and adventure oriented. More like Costa Rica than Emily might be expecting.

1 month ago
Reply to  Jenna

Some of our favorite places to eat in Kauai are casual and in less touristy places. Kenji Burger and Verde are two we’ve repeatedly gone to. We usually enjoy Merriman’s Poipu and Duke’s, which do get more of a tourist crowd.

1 month ago

Great options and you look amazing. That swim dress is bangin’! Love Kauai! We stayed in Hanalei last summer, which was super casual, (bikini strolls through town). Have a wonderful, restorative vacay.

1 month ago

Those looks are so cute on Emily! My go-to sun hat has been the Solumbra Sun Hat from Sun Precautions, it has spf 50 lining the brim. Nuff said, SPF FIFTY!

1 month ago

Have so much fun in Kauai! If you haven’t solidified lodging, I can’t say enough about 1 Hotel Hanalei Bay. It has ruined us for every other hotel on earth. If you’re not staying there, they have two amazing restaurants – 100% worth a drive over for breakfast or dinner. The views are among the best on the island. Also highly recommend the food trucks in Kapaa, kayaking in Hanalei Bay (ask for La’a and Kama, two local 20 something who will tell you every hidden gem in the island), a sunset sail to the west coast where they shot the epic Jurassic Park scenery (BUT TAKE THE DRAMAMINE, they aren’t kidding). The sea turtles come on shore at Poipu and it’s so awesome if you’re not stuck in a crowd of like 200 people 😑. Lydgate Farms chocolate tour was amazing. I was nervous for a three hour farm tour and chocolate tasting, but the kids loved it. Hands down best family trip of our lives (our kids are very close to your kids’ ages, and same older boy/younger girl) – have so much fun!!

1 month ago

Emily, you look truly amazing and like yourself/ confident in these outfits! Love your content overall, but this one in particular, was quite on point! Enjoy your holidays with your beautiful family! ❤️

Ruth Allen
1 month ago

The farmers’ markets all over Kauaii are full of fresh and hyperlocal fruits and veggies. Highly recommend!

1 month ago

Bought look two from top to bottom!
also got the dress in navy, which does not, unfortunately, have the same thick fabric.

also got the Anthro white blouse!

thank you?

1 month ago

Wait. Silver bags are on trend? Hmmm… could you correct the link? Im curious.

1 month ago
Reply to  Sarah

The silver bag is the the Magazine Tote Bag in Metallic Leather from Madewell.

1 month ago

I agree with Emily’s comments about family holidays too but have a few tips: 1. If you can (really depends on the child) see if you can train them to nap in a pram/stroller. The number of times the stroller nap saved us on holidays (especially when our older child stopped napping) so we could keep staying out for the day – on our last holiday (Singapore) our 4 year old would just happily dose in the stroller if he thought what we were doing was BORING. It was a total lifesaver and worth having a decent quality travel stroller. 2. It takes time and effort but you can train most kids to do “adult” things but in a fun way. I really don’t like the beach and I LOVE city holidays. I find the balance is like Emily said, to meet your kids where they are. For example I love museums and art galleries and my boys (7 and 4) love things that are weird and gross. Every big art gallery will have something they like – find the gallery with all of the war paintings, or nude sculptures they can giggle at or modern art that they can… Read more »

1 month ago

Sorry, I’m confused. Where is the blouse in the third look from? A past collection of Emerson Fry, is that right? Thank you! These are great finds.

1 month ago
Reply to  Chelcy

It’s the Mandarin Collar Top in Sunday Stripe Bluesy Organic from Emerson Fry. It’s currently sold out, but they have a waiting list.

1 month ago

You look radiant in all of these! Agree that Kauai is very casual and Tevas & a pair of Havaianas may be all you need. My favorite looks are the Tuckernuck caftan, Kramer chic set and the Emerson Fry blouse w/those amazing olive shorts. All the swimsuits you posted recently look incredible on you, so I think that may be the toughest choice by far ;). Have a wonderful time!

Lisa H
1 month ago

Love the outfits, and the joy on your face while thinking about vacationing on Kauai! I agree with other posters that Kauai is very low key, and outdoorsy. Bathing suit and coverups all day, sandals you can hike in. Swim in the pool, shower, siesta, and then a breezy dress for dinner. We took a fun food tour with Tasting Kauai. Since your kids might not be foodies, maybe you and Brian could each take a turn, on a different part of the island, while the other has a pool or beach day with the kids. We ate some amazing food, including poke, a food truck, and ice cream. We ended up touring the kukuli’ula farmers market with a guide, tasting along the way. So fun! You could get some great restaurant/food truck tips! I have two of the Emerson Fry blouses. Love them! When I popped into their site, I saw they have some great sample bundles available! PS. Our kids are grown now, but we had a great vacation when they were little. We stayed at a resort with a kids camp. For two hours every morning we could lounge by the pool by ourselves! What a… Read more »

1 month ago

Thank you for usually sharing your sizes!! This is SO helpful when the rest of us are shopping (mainly) online and you’ve said it runs big or small and what size you’ve preferred. So again, thank you thank you thank you! Please never stop. 😍

1 month ago

I love Kauai! You’ll have a blast, as will the kids. It’s super casual, and I usually live in a suit, tank or loose top, cut offs, or loose dress, with flip flops or Tevas. I usually bring one comfortable maxi dress that can be dressed up with wedges if I have a nice dinner planned. And appropriate clothes for hiking and kayaking, as needed. Depending on where you are on the island the weather can change a lot. My daughter loves snorkeling, and we usually make it to Ke’e, Anini, and Poipu Beach, at the very least. I love the shops at Hanalei, and the lookouts at Waimea Canyon. The first 2 miles of the Kalalau trail are also amazing (you need to reserve a shuttle or parking pass to go to Ke’e, where the trailhead starts). I’ve also really enjoyed kayaking on Wailua River. The train and tour at the Kilohana Plantation is also worth it. I could go on and on, but you said you already planned it all out. Please share! I’d love to see what you decided to do!

1 month ago

Thanks for the ideas. Hope you have a great spring break! In addition to other suggestions here such as the kalalau trail and waimea canyon, our family with similar aged children enjoyed the mountain sugar cane plantation tube float tour. It was both historical, adventurous at times and something different.