A Classic and Practical Summer Wardrobe

We live in Hawaii, the land of perpetual summer, and after 2 years here I’ve managed to create a bit of a summertime “wardrobe.”  I have a closet full of clothes but tend to default to the same classic pieces time after time.  Most everything can be mixed and matched and they’re all pretty simple and timeless so they won’t go out of style any time soon.  If you’re looking to spruce up your summer style while also keeping things nice and classic this post is for you!  I have most of these pieces, or they’re substitutes for items I have that are older and no longer available.  (You can also see my classic spring wardrobe picks here.)

If you like this kind of post and you need or are in the market for any of these items I’d be incredibly grateful if you shopped after clicking my links.  These posts take hours to put together and your support through affiliate links (I receive a small commission if you shop and it doesn’t cost you any extra) help make these posts worthwhile.  Even if you end up buying something different from the store after clicking a link I’ll still receive “credit,” so don’t feel like you’re stuck only shopping the exact things I’ve shared.  Your support is appreciated!


timeless summer style - classic summer style - preppy summer clothes - anchor baseball cap - striped rash guard - best denim shorts - jean shorts - navy swimsuit - navy blue bikini - gingham maxi dress - Jack Rogers sandals - espadrille wedges - gold birkenstocks - boat and tote bag - straw basket bag - rattan earrings - bow sun hat - scalloped tank -scalloped skirt - pink waterproof birkenstocks


1.  Rattan Earrings. You’ve probably seen me wearing these earrings nonstop since I bought them 6 months ago.  They are SO good, and you seriously cannot beat the $11.99 price tag.  Super light weight and they go with everything!

2.  Navy Embroidered Top. I have last year’s version of this top and I love pairing it with denim shorts and white jeans.  Nice and simple but kind of dressy without feeling dressy.

3.  Bow Sun Hat. I have this navy one as well as the cream one and they’re such great sun hats.  Super feminine with the bow!  Plus they’re packable so it’s ok if they get crushed, and they are adjustable so they’ll fit almost anyone’s head.  They also make it with a striped ribbon, a black ribbon and a pink ribbon!

4.  Gingham Maxi Dress.  I’m all about maxi dresses these days and this one is nice and preppy and easy breezy.  I just ordered it and can’t wait for it to get here.

5.  Anchor Baseball Cap.  I’m baseball cap obsessed.  They’re just so good when you don’t feel like doing your hair or when your chasing toddlers on the beach.  This one is right around $10 and I have it and 100% recommend it.

6.  Simple White T-Shirt. I own two of this exact shirt because I love it so much.  There is a tiny bit of visual texture to them so they aren’t flat white.  I sized up to a medium for an oversized fit.

7.  The Best Denim Shorts. I’ve waxed poetic about these shorts for over a year now…they are the best denim shorts you’ll ever find.  I’m 127 lbs and 5’5″ and wear the 26.  They’re nice and stretchy but they don’t stretch out or get baggy.  An absolute staple in my wardrobe.

8.  Eyelet Camp Shirt. I have 2 white camp shirts (short sleeved button down shirts) and 2 white eyelet tops and I love that this top combines both styles!  I don’t have this one but it’s on my list.  The description says it’s a tad boxy, which is how camp shirts are supposed to fit.  Perfect for a French (front) tuck!

9.  Navy Dreamcatcher Earrings.  I’ve had these earrings since Christmas and they are some of my favorite earrings (I also have the raffia pair that I got 3 compliments on in 5 minutes at church last Sunday).  They’re well made and dress up so many outfits.  More of a splurge but 100% worth it.

10.  Jack Rogers Sandals.  I have quite a few pairs of Jacks but this cork and gold pair has been a staple in my closet for around 6 years.  They are perfect for sun dresses or white jeans or shorts.  These sandals come in about a million colors too!  (I size down in Jacks and then stretch them out by wearing them in a bathtub full of water and then I let them dry on my feet.)

11.  Ruffled Navy Bikini Top. I bought this last summer and at first I wasn’t sure what I’d think about the ruffle.  Well, let me tell you, this top is perfection!  It has cups so it’s nice and supportive and it is so flattering.  The ruffles are feminine and not juvenile at all.  Really comfortable too.

12.  High-Waisted Bikini Bottoms.  I don’t have this exact solid pair but I have it in a few different patterns and they fit really well and are ultra-flattering.  Especially if you’re a mom and don’t really want to bare your lower belly like you used to.

13.  Button Front Shirt.  I wish they took better photos of this shirt because I have 3 in this style (in old color combos, as seen here) and it’s one of my very favorites.  The key is to roll the sleeves twice and do a French tuck in the front.  So great with white jeans or denim shorts!

14.  Scalloped Camisole. I have this top in two colors and it’s a perfect summery camisole.  It’s on the dressier side and looks great tucked into high-waisted skirts (as seen in this blog post here) or shorts.

15.  Straw Basket Bag. I’ve owned this bag for over a year and it’s such a great and affordable large basket bag.  Great for the beach or the market or your every day life.  I also own this backpack version of it.

16.  High Rise Denim Shorts. I love these high-waisted and am wearing them now, actually!  They are very high rise and comfy.  I tuck the front of my shirts in to elongate my legs.

17.  Water-Friendly Birkenstock Sandals. I’m obsessed with these sandals.  I got them last year when I realized regular flip-flops just weren’t supportive enough when I was upping my running mileage.  Under $40 and they come in 4 fun colors, though I’m partial to pink.  Super light weight and not slippery at all.  These are my go-to pool shoes.  As for sizing, I’m a true size 8 in normal shoes but ordered these in a 38 (which the website lists as size 7-7.5).

18.  Strapless One-piece Swimsuit.  I bought this ultra-flattering swimsuit when I was pregnant with Caroline (as seen here) and while it’s not a maternity suit the ruching on the sides make it look great with a bump.  Not frumpy at all though!  I sized up to a medium while pregnant, and even though a small would fit better now without a bump, the medium still works just fine.  Comes in lots of colors and I want the hot pink one!

19.  Espadrille Wedges.  I’ve worn these shoes for years and years in every color they’ve ever made and they’re pretty much the only non-flats I’ll wear because they’re so comfy.  They fit true to size.  Can’t recommend these enough

20.  Scalloped Skirt.  This skirt is so cute.  I love the paper-bag style waist and it fits so well and is extremely comfy.  And it has pockets!  I have this moss green one and the periwinkle blue one too.  (as seen here)

21.  Striped Rash Guard. This blue and white striped rash guard is a recent purchase (I got an XS regular and it fits great…it definitely runs a bit large) and I’m already obsessed.  Great to wear over a bikini or a one piece to help protect your skin from the sun.

22.  Rose Gold Birkenstock Sandals.  Ahhhh, my beloved sandals.  I can’t make myself stop wearing these sandals.  (They’re listed as “metallic copper” but read more as a gold/rose gold in real life.)  They are the comfiest shoes ever and they have the soft foot bed which makes them more comfortable than the regular cork Birks.  The gold color and the white sole make them look a bit more feminine even though they’re the most practical shoes around.  As for sizing, I’m a true size 8 in normal shoes but ordered these in a 38.  If you’re unsure of your Birkenstock size it can be helpful to go to a store that sells them so you can figure out your size and then order the pair you need.  That’s what I did and it helped ease my mind because I knew I’d be ordering the correct size.

23.  Boat and Tote Bags. We have 4 of these bags and I use the medium size with long handles daily as my purse/tote at the gym (navy with navy monogram).  Caroline has a small one with short handles, which I use to keep her stuff in when we go to the gym and when I drop her off in the church nursery (caroline is monogrammed in all lowercase and it looks so cute).  We also have 2 large ones with long handles, which we use for the beach (pink with my navy monogram and navy with JACK monogrammed in navy).  Can’t recommend these enough.  Definitely get them monogrammed for an extra $8!

Katie Vail
Katie Vail

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  1. Liza
    May 15, 2019 / 4:17 am

    I absolutely love this post, as a stay at home mom, it simplifies shopping so much to get some recommendations! We have almost the same exact measurements – although I will say clothes look a heck of a lot better on you than they do on me 🙂 It would be even better, if that’s possible, to mention the store and price range of each item, along with an extra photo of the item so we don’t have to scroll up and down from the description to the composite photo. I love love love hearing all of your thoughts on each of these items, and I ordered the shorts! So hard to find shorts that fit snugly but don’t get baggy. I just found your blog this week and I am loving reading all of your archived posts ! Thank you for your service <3

    • May 15, 2019 / 10:32 am

      Hi Liza, thanks so much for taking the time to read and comment! It makes me so happy to hear you enjoyed this post! Thank you for that recommendation too, I’ll try to be better about including store and price. I’ll try to figure out a better way to make it so you don’t have to do so much scrolling. I try to avoid the extra pics because in order to do that I have to have them all individually saved to my computer and that ends up taking up time and space on my computer when I’m already making a collage, but I’ll brainstorm a bit and check out some other blogs to see if there is a better way. Hope you love the shorts as much as I do! The fact that they don’t get baggy is a game changer…you can seriously wear them 10 days straight and they’ll still fit great!

      • Liza
        May 19, 2019 / 5:36 am

        You’re the best. Also, I totally forgot to head to target yesterday, so I loved your recommendation today to check for returns during the next 14 days. That pink popover looks adorable on you!!

  2. Karen
    May 16, 2019 / 6:00 am

    Love this post! It’s so helpful and such a time-saver! Couple questions: for the (non-waterproof) birkenstocks, is the color that you have called “metallic copper” on the website, or is the rose gold color sold out? 🙁 The website makes the copper color look more orange-y than yours do and I love the look of yours more (maybe they’re the same, I just can’t tell!) Also I’m a little lost on birk sizing… can you share your regular shoe size and what you wear these in? Last question–love the look of the scallop skirt but I’m wondering if you have to iron it/if it wrinkles easily. Super cute but I hate stuff that has to be ironed! Thanks again so much for this helpful post–happy to use your links once I decide to buy! 🙂 –Karen

    • May 16, 2019 / 8:28 am

      Hi Karen! Great questions, and I’ll update the post to help make things more clear. The Birks I have are the metallic copper ones! They aren’t as orange as they look in the pictures. As for sizing, I’m a true size 8 in normal shoes and comfortably wear a 38 in Birks. These say that they’re narrow, but I find that regular birks actually run really wide so to me the “narrow” label is more like a normal shoe rather than actually narrow. I wasn’t sure about sizing either so I went to a place that sold birkenstocks to help figure out my size and then I ordered the pair I needed once I figured that out. As for the skirt, I don’t think it gets all that wrinkly. It’s a relatively thick fabric so it holds up well. Hope all that helps!

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