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The Best & Worst Dresses Over 40

May 22, 2023 By: Nada Manleycomment

You can’t make a whole video about a single dress, can you? Because I almost did. This video idea came to me when I discovered the perfect dress. And we all know that’s like finding the fabled needle in a haystack.

I kind of pride myself on finding needles-in-haystacks, from truly comfortable heels to well-priced high-quality bags. It’s kind of my thing.

And so when I found this dress, I wanted to shout it from the rooftops. I found THE dress!!

Now, a dress can’t be perfect in general. It needs to be perfect in specific. In other words, it needs to be the perfect dress for an area of your life.

This magical dress is the perfect EVERYDAY dress for me. I have dressier dresses and more statement-y dresses and date-night dresses, but this is my absolutely current favorite everyday dress. It checks all the boxes:

  1. It’s woven, not knit, so it doesn’t cling to lumps and bumps and won’t show underwear lines
  2. It doesn’t wrinkle easily.
  3. It’s comfortable!
  4. It’s light and breezy but has sleeves for a little coverage and warmth indoors.
  5. Most of all, it’s SO CUTE! I feel adorable wearing it!

This post is dedicated to dresses just like that: Easy effortless everyday dresses that also happen to be cute! And you can find them all here.

So what’s the magical mystical dress…? Read on to find out. Today, I share 5 tricky, less-than-flattering dresses and 3 chic and comfortable options to try instead!

First, let’s start with the dicey dresses.

The PICS below are linked for easy shopping!!

5 Tricky Dresses

These dresses aren’t all bad. They’re just, for the most part, hard. And who needs hard? I want my casual everyday dresses to be easy and comfortable, the kind of thing I can throw on without a second thought.

  1. The Jersey Dress: Jersey dresses, especially jersey maxis, can be a little unforgiving. The problem is that many of them use very thin flimsy fabric that shows all the lumps and bumps and forces you to go commando to avoid panty lines. Plus, depending on the style and the pattern, they can look dated. You can find all of these here. Pics of the good dresses are also linked.

Skip These:

And Try These

Caslon Jersey Maxi $39
Boden V Neck Jersey Maxi $130
Michael Stars Solange Dress $118

The Too-Sweet Dress

Babydolls are back, and buyer beware. While a touch of sweetness is fine, and I’m all for feminine styles, when a dress is short and frilly and pink and floral and ruffled and… In order to get the sophisticated look we want, skip the super-sweet styles and stick with something a little more balanced.

You can find all of these here. Pics of the good dresses are also linked.

Pink and floral and ruffles make this dress a little bit too sweet.
This dress has too much going on and is too youthful to be chic.
This Bebe dress, $169, strikes the perfect balance.

The Shapeless Dress

Shapeless shrouds have been marketed at women over 40 for ever, with the idea that more fabric hides more cheesecake. This is not only false, but it’s also wildly unflattering. If you want to go for a flowy and shapeless style, keep it short for balance and flattery.

This dress isn’t short enough to be this oversized.
This looks like a rectangular block of fabric.
This Karen Kane dress has a relaxed silhouette but a flattering length.

Dated Ruching

Ruching is magical when done correctly, but it can also look dated and like you’re trying to hide behind layers of extra fabric. You can find all of these here. Pics of the good dresses are also linked.

The ruching on this dress is dated.
This Eliza J dress, $64, is so chic and features subtle ruching.
A stylish ruched option from Tahari.
This ruched dress from Cinq a Sept is modern and chic.

The High Low Dress

The problem with a high-low dress is not that it’s dated, because it is not. It’s currently really trendy. It’s just kind of hard to pull off, especially for petites. If you love this style, keep the front above the knee and the back not that long for balance.

You can find all of these here. Pics of the good dresses are also linked.

A bad high-low style
MAC DUGGAL cocktail dress $398
Ileena for Mac Duggal floral dress $298
CeCe floral dress $103

3 Dresses That Work For Every Woman

Yes, I know that’s a bold claim. And I’m prepared to stand behind it. With few exceptions, there’s a dress here for almost every woman, and these dress styles, in general, are more or less universally flattering.

Let the comments begin! :)

Seriously, though, as far as casual everyday warm-weather dresses go, this roundup is chic, flattering, and pretty timeless.

You can find all of these here. Pics of the good dresses are also linked.

The Shirtdress

From easy and relaxed to crisp and polished, this style comes in an unlimited number or styles, options, and fabrics. A shirtdress is a classic style that buttons up the front, with or without waist definition.

Here, some of my fave shirtdresses of spring 2023, in no particular order.

You can find all of these here. Pics of the good dresses are also linked.

Nadine Stripe Long Sleeve Cotton Poplin Shirtdress RAG & BONE $31
Coral Island Cotton Gauze Midi Shirtdress TOMMY BAHAMA $158
Boden Revere Collar Maxi Shirt Dress
Mary Long Sleeve Shirtdress FRANK & EILEEN $328
Talbots linen midi shirtdress
CINQ À SEPT Lucilla Shirtdress
KAREN KANE Stripe Long Sleeve Shirtdress

The Swing Dress

Characterized by its shorter, flowy shape, the swing dress can have sleeves or not, be tiered or plain, and solid or patterned. It’s main characteristic is a flowy silhouette that starts just under the bust or in some cases at the waist. It’s generally breezy and easy and super comfortable.

You can find all of these here. Pics of the good dresses are also linked.

Rainy Long Sleeve Cotton Gauze Shirtdress XÍRENA $285
Daisy Long Sleeve Dress MILLE $228
Scarlett Flutter Sleeve Linen & Cotton Dress BEACHLUNCHLOUNGE $68
Lightspun Button Front Tiered Midi Dress MADEWELL $128
Clip Dot Ruffle Long Sleeve Shift Dress CECE $74.25 – $99.00
Tie Back Tiered Cotton Minidress TREASURE & BOND $49

The Tunic Dress

This is the dress that start it at all. A breezy linen, cotton, or blend tunic in a straight shape at a length that flatters you is easy, comfortable and chic. Pair it with flat sandals or espadrilles and be prepared to enjoy summer. This is the magic dress I referred to in the beginning of this post, and here it is!

This is the Freesia dress from Splendid, and I picked it up at Marshall’s. It is still available in limited places, like Ebay and Outlet stores, and I’m obsessed. If you don’t love this black/white color, it’s also available in olive.

You can find all of these here. Pics of the good dresses are also linked.

If you think you want to give this tunic-style dress a try, here are some other options:

Champagne Collier Dress TUCKERNUCK 100 $198
COLETTE LINEN MINI DRESS Product Selections $160
120% LINO Orchid Pink Linen Dress $206
Embroidered dress Crinkle cotton & linen $269
Navy Long Sleeve Classic Tunic Dress with Ric Rac $65.00
Ravenna Linen Dress Was $150.00; Now $129

What did you think of this roundup of dresses? And did you find a new summer favorite? Let me know in the comments!

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