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Preppy Modest Midi Dresses

This edit gathers 796 preppy modest midi dresses from the modest-fashion boutiques we track. Every piece has a preppy, polished look on top of a modest neckline and a midi length. Prices start around $17, and the list refreshes daily as stock changes.

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Sister Jane Alice jacquard frill hem midi dress with removable lace collar in blue
ASOS
Sister Jane Alice jacquard frill hem midi dress with removable lace collar in blue
$182.00
Sizes at store
Color Block Taffeta Shirtdress
Teri Jon
Color Block Taffeta Shirtdress
$465.00
4614161822
Quinn Pintuck Midi DressFinal sale — 30% off
Mestiza
Quinn Pintuck Midi Dress
$595.00$417.00
24681012+1
Jovana | Burgundy Hand-Embellished Crew-Neck Midi Dress With Drop Waist
Club L London
Jovana | Burgundy Hand-Embellished Crew-Neck Midi Dress With Drop Waist
$252.34
Sizes at store
Good Feels Slim Midi Dress
Free People
Good Feels Slim Midi Dress
$60.00
Sizes at store
Rails Vivier Ruffle Smocked Midi Dress
Bloomingdale's
Rails Vivier Ruffle Smocked Midi Dress
$278.00
XSSMLXL
Threadbare boat neck midi dress with seam detailing in chocolate brownFinal sale — 25% off
ASOS
Threadbare boat neck midi dress with seam detailing in chocolate brown
$48.00$36.00
Sizes at store
Ted Baker Charlie Drop Waist Linen Shirt Dress
Bloomingdale's
Ted Baker Charlie Drop Waist Linen Shirt Dress
$325.00
SMLXL
Jason Wu Collection Chiffon Pleated Midi Dress
Bloomingdale's
Jason Wu Collection Chiffon Pleated Midi Dress
$1,795.00
468
Nobody's Child Saylor short sleeve draped maxi dress in light beige
ASOS
Nobody's Child Saylor short sleeve draped maxi dress in light beige
$137.00
Sizes at store
AWARE glitter jersey cowl neck cami midi dress in black and silverFinal sale — 45% off
ASOS
AWARE glitter jersey cowl neck cami midi dress in black and silver
$70.00$38.50
Sizes at store
a. ren Blythe Cotton Blend Short Sleeve Midi DressFinal sale — 20% off
Bloomingdale's
a. ren Blythe Cotton Blend Short Sleeve Midi Dress
$98.00$78.40
XSSML
Black Cami Bodycon Slip Dress by AngeleyeFinal sale — 31% off
Goddiva
Black Cami Bodycon Slip Dress by Angeleye
$39.56$27.28
XSSMLXL
Sleeveless Mikado Fit And Flare Midi Dress With V-Back In Electric IceFinal sale — 30% off
Adrianna Papell
Sleeveless Mikado Fit And Flare Midi Dress With V-Back In Electric Ice
$169.00$118.99
8101214
Chinti & Parker Women's Cotton Cherry Swing DressFinal sale — 25% off
Bloomingdale's
Chinti & Parker Women's Cotton Cherry Swing Dress
$275.00$206.25
XSSMLXL
The Owen Pleated Waist Dress in Rust
Piper & Scoot
The Owen Pleated Waist Dress in Rust
$63.00
S
Marcina Dress
Reformation
Marcina Dress
$278.00
Sizes at store
Hobbs London Kristen Dress
Bloomingdale's
Hobbs London Kristen Dress
$335.00
468101214+1
Teri Jon by Rickie Freeman Crepe Asymmetrical Dress
Bloomingdale's
Teri Jon by Rickie Freeman Crepe Asymmetrical Dress
$640.00
2481014
Ramy Brook Vivienne DressFinal sale — 72% off
Bloomingdale's
Ramy Brook Vivienne Dress
$465.00$130.20
XL
ASOS DESIGN high neck scarf detail maxi dress in green
ASOS
ASOS DESIGN high neck scarf detail maxi dress in green
$84.99
Sizes at store
Topshop dropped waist poplin mix open back midaxi dress in black
ASOS
Topshop dropped waist poplin mix open back midaxi dress in black
$65.00
Sizes at store
ASOS DESIGN linen mix maxi vest dress with poplin skirt in navy and white
ASOS
ASOS DESIGN linen mix maxi vest dress with poplin skirt in navy and white
$94.99
Sizes at store
3.1 Phillip Lim Poplin Trapeze Midi Dress
Bloomingdale's
3.1 Phillip Lim Poplin Trapeze Midi Dress
$595.00
XSSML

Frequently asked questions

What is a preppy dress?
Collars, buttons, stripes and structured shapes -- polished enough for the office or a school event.
Are these dresses actually modest?
Yes. Every dress here is tagged with a modest neckline, a midi length, and we exclude sheer, cut-out, open-back and mini styles by default.
How much do these cost?
Prices start around $17 and run up from there; each card shows the live price and links straight to the retailer.
How often is this collection updated?
It refreshes daily -- new arrivals are added and sold-out pieces drop off automatically, so what you see is in stock.