12 Cute, Comfy Easy-To-Wear Spring Break Outfits – Emily Henderson

12 Cute, Comfy Easy-To-Wear Spring Break Outfits – Emily Henderson

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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).

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 Is 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).

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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.

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

*Photos by Kaitlin Green

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