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It's Ashley Robertson · Apr 29, 2026

The Pieces Doing All the Work For Me This Summer

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Ashley Robertson · It's Ashley Robertson

Summer is shaping up to include a few trips, and while I’ll always love shopping, I’ve found I actually prefer having a handful of key pieces I can wear on repeat. So this is what I’m leaning into this season: a small, mix-and-match wardrobe that works across the board.

I broke it down into a resort section, a few easy outfits that can be reworked multiple ways, some chic casual looks for lunches, dinners, and anything in between, and then the accessories and shoes that I feel like you can wear on vacation or a cute happy hour around town.

Resort-wise (or pool), I’ve kept it very simple and just bought a few pieces that I know I’ll actually wear on repeat.. with maybe a few trendy pieces to throw in the mix.

A really good one-piece is non-negotiable for me right now. I’ve also been bringing the same beach bag on every trip (it somehow fits everything from books to trucks and shovels without turning into a black hole). And then a go-to straw hat that I’ll wear at the pool, to the beach, and honestly even at soccer games.. basically anything that requires being outside for more than five minutes.

White Cover Up | Raffia Hat | Wrap Sandals | Raffia Large Tote | Shell Necklace | Poplin Dress | Sunglasses | One Piece Swimsuit

I also love to buy a few stand out pieces that are fun and keep a pulse on trends without me regretting my purchase later. Like this colorful pareo, which is currently in my cart for an upcoming trip to Palm Beach.

Lets’ break down the items into looks. Starting with hero pieces:

Look One: This maxi lace coverup is beyond chic and will make any swimsuit look like a million bucks. Throw on a bucket hat with this tote and a chic sandal.

Look Two: The black eyelet coverup dress (this also comes in white) with my favorite high waist bikini bottom (I wear a medium) and this triangle top.

Look Three: A pink one piece swimsuit with the colorful pareo (we also can pair this with the brown bikini).

Look Four: A lace mini dress cover up with this the pink one piece swimsuit. I would keep everything really light and tonal. These gold sandals and bucket hat.

Look Five: This poplin dress also really stands out to me as a nice post-swim look. I never want anything snug after a day in the sun. I love that over a swimsuit with wrap sandals and this tote.

Maxi lace Coverup | Bucket Hat | Brown Bikini | Black Raffia Tote | Eyelet Coverup Dress | Pink One Piece Swimsuit | Gold Sandals | Wrap Sarong

This is the category I wear the most, easy dresses, something lightweight to throw over my shoulders for when it’s inevitably freezing inside, and linen pants that don’t feel like a risk.

I’ve also been into a good short set lately because it just makes getting dressed easier and still feels pulled together.

Lets’ break down the items into looks. Starting with hero pieces:

Look One: This long drop waist dress (I wear a 4) paired with a light knit (I got the XS) over the shoulder.

Look Two: The black mini dress with the same knit over the shoulder or around the waist.

Look Three: Obsessed with this matching skirt and vest. I just bought this for my upcoming trip to Palm Beach.

Look Four: The knit sweater with the skirt—I wore this in Sonoma recently.

Look Five: The white tee with the linen pants, oversized sunglasses and this necklace.

White Maxi Dress | Cream Cardigan | Yellow Vest | Black Mini Dress | Yellow Maxi Skirt | White Button Shirt | Sunglasses | White Midi Skirt

Lets’ break down the items into looks. Starting with hero pieces:

Look One: I love a matching set and this linen top & pants are chic but equally casual and comfortable. Pair with this mesh bag and oversized sunglasses.

Look Two: The white mini dress (I just ordered this) with the gold wrap sandals and the shell bag.

Look Three: My favorite t-shirt with these lace shorts. Pair with this mesh bag and oversized sunglasses.

Look Four: I have several of these short sets from Amazon. Wear with the lightweight knit over your shoulders and the Fendi flats.

Look Five: The khaki mini dress is one of those throw-and-go types. I’d pair with this white clutch and the Fendi flats.

Lace Shorts | White Dress | Khaki Dress | Linen Top & Pants | Mesh Bag | White Tank | Blue Matching Set | White Tee

This is where I mix it up a bit. Shoes, bags, and accessories that are doing most of the work. Still classic, but with a little trend mixed in, so everything feels current without trying too hard.

I feel like everyone needs a good flip-flop for the pool, that doesn’t look like a pool shoe. And what I call a fancy flat. I wear these with mini dresses, etc., and they look intentional but still read “summer casual”.

I also have a lot of pieces from the brand Julietta and they really are “outfit makers”. These necklaces are absolutely worth every penny and look so chic styled.

Sunglasses | Heeled Mules | Bucket Hat | Clutch Bag | TKEES Sandals | Seashell Bag | Bangle Bracelet | Seashell Necklace

Read the original on ashleyrobertson.substack.com

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