Modest fashion in Annapolis, Maryland thrives in every corner of this historic seaport. From charming Main Street boutiques to well-loved mall favorites, you’ll find thoughtfully-cut dresses, classic skirts, and layer-ready tops that let you honor your values while looking polished for work, worship, and weekends.
Browse Modest Clothing Stores in Annapolis
Wrabyn Boutique
What Does This Store Provide:
This upscale boutique curates timeless blouses, skirts, and dresses from independent designers, then pairs them with one-on-one styling appointments that make modest dressing effortless. It’s a favorite stop for women seeking quality fabrics and elegant silhouettes that last beyond a single season.
What Shoppers Appreciate The Most:
- Personalized styling sessions
- High-quality classic pieces with modest cuts
- Relaxed boutique atmosphere
The Cottage on Main
What Does This Store Provide:
Known for bright coastal colors and tasteful prints, The Cottage stocks sundresses, midi skirts, and easy layering pieces that offer coverage without sacrificing style. It’s ideal for ladies who love a breezy, beach-inspired look that still keeps hems and necklines modest.
What Shoppers Appreciate The Most:
- Coastal-chic dresses perfect for layering
- Thoughtfully chosen accessories to finish an outfit
- Warm, local staff who remember regulars
The Lucky Knot
What Does This Store Provide:
If you love crisp stripes, anchor motifs, and classic shift dresses that hit the knee, The Lucky Knot is your harbor. Their preppy collections make modest layering simple—just add a cardigan or scarf and you’re ready for brunch on the bay.
What Shoppers Appreciate The Most:
- Cheerful nautical prints with coverage
- Easy-to-layer shift dresses & cardigans
- Lively Main Street vibe
Scout & Molly’s Boutique – Annapolis Town Center
What Does This Store Provide:
This franchise-style boutique keeps pace with current trends while curating silhouettes that aren’t overly revealing. Expect flattering midi lengths, elevated basics, and plenty of layering pieces that make it simple to build a polished, faith-friendly wardrobe.
What Shoppers Appreciate The Most:
- On-trend modest silhouettes
- Size-inclusive racks XS–XXL
- Engaging stylists who curate outfits
Soft Surroundings – Westfield Annapolis
What Does This Store Provide:
Soft Surroundings focuses on breathable fabrics, generous cuts, and artisan details that flatter without clinging. Women of every age love its linen tunics, flowing maxi skirts, and cotton tees that keep coverage comfortable year-round.
What Shoppers Appreciate The Most:
- Ultra-soft fabrics that breathe
- Relaxed-fit layers for coverage
- Welcoming multi-age clientele
J.Jill – Annapolis Towne Centre
What Does This Store Provide:
J.Jill is famous for breezy knits, easy layers, and neutral palettes that make mix-and-match modest outfits simple. Petite, tall, and women’s sizes keep every body type covered—literally.
What Shoppers Appreciate The Most:
- Breezy knit tops and skirts
- Petite & plus size range
- Easy-mix neutral palette
Talbots – Westfield Annapolis
What Does This Store Provide:
Talbots’ polished blazers, midi skirts, and button-front blouses are longtime staples for modest dressers. Their size spectrum, including petite and plus, makes it easy to find a flattering, coverage-conscious fit.
What Shoppers Appreciate The Most:
- Timeless blazers & midi skirts
- Broad size options in petite & plus
- Reliable quality that endures
Whimsicality
What Does This Store Provide:
This family-run boutique blends modest floral dresses with unique local gifts, so you can update your wardrobe and pick up a charming hostess present in one stop. Its curated racks lean feminine and flattering without straying into skimpy territory.
What Shoppers Appreciate The Most:
- Playful yet modest dress selection
- Unique local gifts alongside apparel
- Cheerful family-run service
Find A Modest Clothing Store In A City Near Annapolis
Bowie, Maryland Baltimore, Maryland College Park, Maryland Greenbelt, Maryland Laurel, Maryland Rockville, Maryland
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