Modest Dresses You Will Want For Summer And Beyond

Can you believe we only have a few more weeks of summer? Labor Day is just around the corner and even though that’s when we start to dip our toes in fall fashion (my favorite time of year), I’m always still a little bummed out to see summer left behind. However, summer is not over yet and we still have plenty of warm weather to enjoy. I love this time of year because I can still wear my summer dresses. But I’m starting to think about how I can work them into the fall transition, especially as the nights start to get cooler. That means finding midi-length styles that may not show so much skin, and can be a little more modest and covered up. So I wanted to take this post to discuss a great one piece outfit: the modest summer dress. I’ll show you some of the best modest dresses for summer and fall.

Modest Dresses For Summer And Fall

A modest dress is a piece that I love because it is incredibly sophisticated and perfect for women over 40. Don’t get me wrong, there is nothing wrong with showing a little skin, but I feel like there is an air of silent confidence that women exude when they are wearing a sexy modest or midi-length dress. This is not a new trend. This style of dress has made its way to us throughout the decades, more notably from the 1940s with iterations of it up to present day.

One of the most iconic designers that has created this perfect silhouette is Diane von Furstenberg. Her pre-fall and fall 2019 collections didn’t stray from her iconic dress styles. We can look to her collections for perfect pieces to take us into fall as well as impeccable styling ideas, like layering a dress over pants! We can also talk about designer Tadashi Shoji, who is the master at dressing a woman’s body. His fall 2019 collection featured beautifully draped fabrics in rich colors like navy and plum that can be perfect for late summer and also transition into early fall and beyond. Bonus points that he truly knows how to dress women of all sizes and featured plus models in his show. I love that his models look like women you see in real life and his looks are truly something to aspire to.


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modest dresses for summer and fall fountainof30How To Wear Midi-Length Modest Dresses

This style of dress makes for the perfect seasonal transition piece and you can wear it practically anywhere. For the late summer months (just like what we are experiencing now) I love something that is sleeveless or with short sleeves. It will help keep you cool but you can add layers if you work in a chilly office or are out during a cool evening. This Tory Burch sweater dress is great for a day at the office and transitions well for evening drinks or even a school event. I also love the darker, almost Goth vibe of this Endora Midi Dress from Anthropologie. It’s right up my alley and I would wear this with my favorite leather jacket and black ankle boots in the fall. I would also wear it alone right now with a pair of black flat sandals.

Styling Tips for Summer to Fall Dresses

1. Modest dresses are like one stop shopping. You can pull one on and don’t really need to worry about anything else. They do all of the work for you. However, they are incredibly versatile in the sense that you can add different types of accessories and shoes to make the outfit you want. I love to take a basic style dress like this Briar Dress from Anthropologie and play it up with some statement platform heels. I practically live in my denim jacket during the late summer, so adding that as a topper will finish off the outfit. It’s simple but thoughtful.

2. If you stock up on this style of dress, you could (in theory) cut your wardrobe needs in half. OK, I may be getting some weird looks, but the versatility of these modest dresses makes them so perfect as transitional pieces, which means you can wear them twice or three times as much throughout the year. Wearing one alone on a hot day in the summer, with a trench and ankle boots in the fall and layered with a chunky cardigan with tights and knee boots in the winter defines a pretty great piece of clothing. Don’t you think?

3. Subtle is sexy. This tip speaks for itself. This style of dress looks great on any type of body regardless of shape or size. The modest dress comes in fitted styles, flowy styles, midi, maxi and sleeve lengths and necklines of all varieties. Pick one that plays up your best features and makes you feel sexy and sophisticated. I love the simplicity and sporty vibe of this Norma Kamali Ruched Midi Dress. It’s just my style as I love to show off my arms but conceal bits of my mid-section.

4. More than one style can work for you. You may be a fan of the classic shirtwaist style of this dress. But don’t get stuck in a rut. The subtle chic vibes of a shirtwaist style can be great for the office but you can also expand and try this Eileen Fisher smock during a causal weekend outing. Try different styles for different occasions to keep your look and wardrobe fresh throughout the changing of the seasons.

5. This is a timeless silhouette, so don’t be afraid to invest in a good piece that could last you a lifetime. As I previously stated, we’ve seen this style of dress for decades. It’s a classic so you shouldn’t feel bad about investing a nice chunk of change on a piece made from a beautiful fabric that you will be able to maintain and wear for years to come. Something in a basic black, navy or camel in a high quality cotton or linen could last you forever and all you need to do is update your accessories as the trends change.

Shop Modest Dresses

(Pictured above from left to right)

Ted Baker London Bluebell Collar Dress, $329

Anthropogolie Endora Midi Dress, $180

Norma Kamali Sleeveless Ruched Midi Dress, $49.97

Anthropologie Briar Buttondown Dress, $98

Mango Buttoned Linen-blend Dress, $79.99

Tory Burch Colorblock Sweater Dress, $398

Eileen Fisher V-Neck Short-Sleeve Lofty Organic Cotton Midi Dress, now $138

– Carmen Turner

Runway Photos: Diane von Furstenberg Fall 2019 and Tadashi Shoji Fall 2019,

You may like to read more of Carmen’s wearable trends posts like What To Wear (and Pack) For Your Summer Vacation and Wearable Trends: 1940s Vintage-Inspired Dresses.

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1 thought on “Modest Dresses You Will Want For Summer And Beyond”

  1. I like to pair leggings with some sleeveless dresses for fall or add a long sleeve tank underneath to make it almost look like a jumper. Remember jumpers? I wonder if they will ever come back in style?


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