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25 YEARS SIDE BY SIDE SALE ENDS TONIGHT

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SHIRLEY™ - CASUAL OVERSIZED BLACK MAXI DRESS

$139.95

$69.95

Save 50%

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30-Day Money-Back Guarantee
Loved by 50,000+ women across America
Size XS

Only a few left in stock!

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UPDATE: As we celebrate 25 years side by side, only a limited number of items remain. Take advantage of our biggest discounts today. The Anniversary Sale ends tonight.

The dress that makes you feel like you got your whole self back.

There is a version of getting dressed that feels like freedom — not adjusting, not second-guessing, not standing in the fitting room talking yourself out of something beautiful. Just on, done, and completely right. These dresses were made entirely for that moment. Flowing fabrics that move with your body rather than against it, silhouettes that drape and gather in all the right places, and lengths that give you the coverage and the confidence to walk into any room and simply feel like yourself — at your most beautiful, most comfortable, most completely you.

  • Flows With You — Soft flowing fabric that moves naturally with your body through a warm afternoon without pulling, clinging, or asking anything of you.
  • Covers and Flatters — Lengths and silhouettes that skim generously and drape beautifully — so you feel covered, confident, and completely at ease from every angle.
  • Arms at Ease — Sleeve styles across the collection that cover the upper arms with a light, elegant fit — no heat, no heaviness, just easy beautiful coverage.
  • On and Stunning — A complete, considered look the moment you put it on — no layering, no second piece, no wondering if it works.

This is an original Madeleine & Ivy California product. If you see this sold through any third party retailer or marketplace it is not genuine. We sell exclusively through madeleineandivy.com.

At Dorothy & James Charleston, your satisfaction comes first. That's why we keep you updated on your order every step of the way — and always offer free shipping across the U.S.

We ship with UPS, so your order arrives safely and on time.

If you don't love it, you don't pay for it. Return any item within 30 days for a full refund. No questions asked. Shopping with us is always completely risk-free. Some exemptions apply. To understand better, read here.

At Dorothy & James Charleston, your peace of mind comes first. Every payment is processed through trusted, encrypted providers. Shop with complete confidence — your information is always safe with us.

Kind Words From Our Customers

I was nervous to order online but the quality blew me away. Fits perfectly and looks exactly like the photos. Already ordered two more pieces!

Patricia H., Nashville, TN

I followed the size guide and it fit like it was made for me. Wore it to church Sunday and three women asked where I got it.

Diane R., Atlanta, GA

Had to return one top and customer service was so kind and easy. Got my refund within days and ordered again the same day.

Carol W., Phoenix, AZ

I thought boutique meant expensive but I got three beautiful pieces for less than one from the department store. My sister ordered the same day she saw me wearing it.

Beverly T., Richmond, VA

Everything in stores is either for teenagers or for women who gave up on style. Dorothy and James is different. I feel like myself again.

Margaret L., Portland, OR

I never spend money on myself but my friend said this sale was a gift from Dorothy and James to me. She was right. Worth every penny.

Ruth Ann K., Charlotte, NC

Arrived faster than I expected and packaged so nicely. The quality is better than anything I've found at the mall. Best online purchase I've made in years.

Sandra M., Columbus, OH

25 YEARS SIDE BY SIDE

Twenty-five years ago, James and I got married.

Over the years, we built a life, a family, and this boutique together.

Every piece we offer is chosen with intention. Made to feel comfortable, flattering, and easy to wear.

To celebrate 25 years of marriage, we're sharing our biggest discounts ever. Our gift to every woman who deserves to feel beautiful.

With love,
Dorothy & James 🤍

Free Shipping

Every order ships free across the U.S. Straight to your door, with tracking included. No surprises, no extra costs.

30-Day Money-Back Guarantee

If you don't love it, you don't pay for it. Return any item within 30 days. No questions asked. Shopping with us is always risk-free.

100% Secure Payment

Your payment is always safe with us. We use trusted, encrypted payment providers so you can shop with complete peace of mind.

Free Shipping

We offer Free Shipping for maximum customer comfort. Your satisfaction is important to us, which is why we offer smooth and free delivery.

30-Day Return Guarantee

Your satisfaction is our focus. Our 30-day return policy guarantees you maximum flexibility and the best shopping experience.

100% Secure Payment

We offer you a variety of secure payment options. Pay easily and enjoy a safe shopping experience.