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Preppy Modest Midi Dresses

This edit gathers 662 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 $22, and the list refreshes daily as stock changes.

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Toccin Gail Button Front Belted Midi Dress
Bloomingdale's
Toccin Gail Button Front Belted Midi Dress
$695.00
XXSXSSML
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
Nobody's Child Petite Quinn satin puff sleeve midi day dress in blue
ASOS
Nobody's Child Petite Quinn satin puff sleeve midi day dress in blue
$137.00
Sizes at store
Sleeveless Collared Belted Midi Dress
Commense
Sleeveless Collared Belted Midi Dress
$79.00
XSSMXL
Teri Jon by Rickie Freeman Taffeta Jacquard ShirtdressFinal sale — 30% off
Bloomingdale's
Teri Jon by Rickie Freeman Taffeta Jacquard Shirtdress
$590.00$413.00
468101214+1
Oscar de la Renta Large Chine Palm Leaves Dress
Bloomingdale's
Oscar de la Renta Large Chine Palm Leaves Dress
$3,990.00
024612
Herve Leger The Alice Dress
Bloomingdale's
Herve Leger The Alice Dress
$695.00
XSSMLXL
YAS cutabout seams mixed fabrics midi dress in mixed blue plaid print
ASOS
YAS cutabout seams mixed fabrics midi dress in mixed blue plaid print
$113.00
Sizes at store
Prosperina Lana Lime Green Cotton Button-Front Midi DressFinal sale — 31% off
Red Dress
Prosperina Lana Lime Green Cotton Button-Front Midi Dress
$168.00$116.00
XSM
Lace Top Chiffon Godet Dress by Double Second
Goddiva
Lace Top Chiffon Godet Dress by Double Second
$115.94
6810121416+3
Simkhai Kristen Sleeveless Midi Dress
Bloomingdale's
Simkhai Kristen Sleeveless Midi Dress
$845.00
0002468+3
Mac Duggal - Beige Boucl Midi Dress with Rhinestone Buttons - Ecru Multi / US 8
Mac Duggal
Mac Duggal - Beige Boucl Midi Dress with Rhinestone Buttons - Ecru Multi / US 8
$558.00
24681012+2
The Odella Denim Dress - Noir
Ulla Johnson
The Odella Denim Dress - Noir
$850.00
0002468+1
Ivory Gold Ball Dress
Monique Lhuillier
Ivory Gold Ball Dress
$2,795.00
14
Hobbs London Hurst DressFinal sale — 20% off
Bloomingdale's
Hobbs London Hurst Dress
$420.00$335.00
246
Good Feels Slim Midi Dress
Free People
Good Feels Slim Midi Dress
$60.00
Sizes at store
Cotton Blend Sleeveless Belted Maxi Dress
Commense
Cotton Blend Sleeveless Belted Maxi Dress
$56.00
XSSMLXL
Sister Jane Alice jacquard frill hem midi dress with removable lace collar in blueFinal sale — 50% off
ASOS
Sister Jane Alice jacquard frill hem midi dress with removable lace collar in blue
$182.00$91.00
Sizes at store
Bardot Melody lace poplin maxi dress in blackFinal sale — 70% off
ASOS
Bardot Melody lace poplin maxi dress in black
$242.00$72.60
Sizes at store
Ghospell cotton rich ruched bow detail midi dress in black stripe
ASOS
Ghospell cotton rich ruched bow detail midi dress in black stripe
$191.00
Sizes at store
& Other Stories sleevless jersey maxi dress with back split in black
ASOS
& Other Stories sleevless jersey maxi dress with back split in black
$96.00
Sizes at store
Simkhai Arlo Belted Maxi Dress
Bloomingdale's
Simkhai Arlo Belted Maxi Dress
$595.00
XSSML
Contrast Trim Collared Smocked Waist Knit Dress
Commense
Contrast Trim Collared Smocked Waist Knit Dress
$49.00
ML
Washable Ribbed Knit Dress
UNIQLO
Washable Ribbed Knit Dress
$14.90
Sizes at store

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 $22 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.