The short answer on Santa Maria Maxi Dress: pick one anchor piece, keep the palette to two colours, and let the shoes decide how formal the whole thing reads. One piece should lead and the rest should stay quiet; two competing pieces read as an accident.
How to Style Santa Maria Maxi Dress

Why this comes up
The short answer on Santa Maria Maxi Dress: pick one anchor piece, keep the palette to two colours, and let the shoes decide how formal the whole thing reads. One piece should lead and the rest should stay quiet; two competing pieces read as an accident. Proportion does more than colour: volume on top wants something narrow below, and the reverse. A dress that fits the shoulders can be taken in anywhere else. One that does not, cannot. The groups below run from the decision that matters most to the ones you make afterwards.
Easy Daytime Dresses

Daira Maxi Scarf Dress
shopsignificantother.com

Daira Maxi Dress
shopsignificantother.com

Aiba Maxi Dress
retrofete.com

SPANX AirEssentials® Sandwashed Drawstring Maxi Tank Dress
Spanx

Vanya Tiered Maxi Skirt
retrofete.com

Kyle Maxi Top
ronnykobo.com

Quincy Halter Maxi Dress With Hardware - Cornflower Blue
Meshki

Louise Satin And Lace Maxi Dress - Black/Ivory
meshki.com.au
What actually decides it
What decides this is shoulder fit, length and how the fabric moves. Everything else is preference. Two from the first group show the range: shopsignificantother.com's Daira Maxi Scarf Dress at $330, and meshki.com.au's Louise Satin And Lace Maxi Dress - Black/Ivory at $249. The first is the considered buy; the second is the one to start with. Lining is what stops a cheap fabric reading as cheap. Check where the waist seam sits on the model against your own proportions. A higher price mostly buys materials and finishing, and occasionally it buys nothing at all.
Dressed Up After Six

Tiffany Fringe Maxi Dress - Plum
meshki.com.au

Shea Maxi Dress - Sky Blue Cream
lspace.com

Luisa Long Sleeve Maxi Dress
Significant Other

Tallulah Maxi Dress Cream - Cream Multi
manymoons.com

Lara 70 Maxi Gancini Pump - Nero
manymoons.com

Cerina Dress in Maxi Heirloom Paisley
J.McLaughlin

Gabby Maxi - Hibiscus And Plumeria Oh My
L Space

Kailyn Maxi Dress in Mythic Floral Geo
J.McLaughlin
How to wear it
A belt turns a shapeless dress into a deliberate one. Let the dress be the loudest thing you own that day. From the second group, meshki.com.au's Tiffany Fringe Maxi Dress - Plum ($449) is the one that earns its place, because it works in more than one context without being restyled. The third group is smaller and deliberately narrower, dresses, for the decisions you make after the main one. None of this needs the whole group. One piece from each is usually enough.
Our honest take
There are 20 dresses here from 13 brands, $68 to $698, all in stock when this was written. We would not buy all of them, and neither should you. Andie's Swim's Womens Relaxed Tee Maxi Dress - Pigment Dye Jersey - Heather Grey at $68 is the low-risk way in, and retrofete.com's Aiba Maxi Dress at $698 only makes sense if this is a category you already use constantly. On santa maria maxi dress specifically: the difference between the top and the bottom of this list is real but smaller than the price gap suggests. Nothing here is included because it is famous, and price is not used as a proxy for quality anywhere on this page. If you take one thing away: pay for the thing that touches your body and economise on the thing that sits on top of it.
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