Casual Dresses for Women over 50 Summer into Fall Edition

If you know me you know of my love for dresses. For me they are timeless, easy to put together and make me feel pretty. As Fall is starting to hit, big hint Mother Nature, it is time to start thinking Casual Dresses for Women Over 50.

There are dresses for everyone with several different necklines and lengths. And big secret many are my Summer Casual dresses just with a few key additions. Yes, adding a sweater or jacket can completely extend the season for your casual dress. To say nothing of adding in a boot or loafer.

Dresses truly can go for any season as I have often shown. Add a little boot, a coverup or even a tee underneath and you are ready to go.

Dresses for Fall for Women over 50

The key is to not discount any style, length or neckline. Be open minded and prepared to experiment a bit. There are always ways to make it work with you and your personal taste. So, lets get started shall we:

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Empire Waist Dress/ Moto Boot / Kimono

1. Empire Waist Dress with Pockets

Tell me it has pockets, and I am there. This fun Empire Waist Dress that I found on Amazon is perfect for any season. The jersey material can also make it casual or dressy your choice. This particular dress has long sleeves, but they also have a short sleeve version. I added a kimono and moto boot for Fall, and I have added leggings and a fur vest for Winter.

2) Mid Length Fitted T-Dress

This Olive and white midi dress has a classic silhouette and looks great when you throw on a light cardigan or denim jacket. The waist is elastic so you can add a belt if you want. For me, the colour is perfect for Fall transition. And ladies ignore the naysayers on Tee Dresses are not suitable for women over 50. If it feels good wear the dress.

3. Old Navy Smock Dress

A linen dress with pockets and a pretty neckline. I have worn this dress with Brogues, sandals and yes even ankle boots for various seasons. I do find a smock dress for the perfect casual dress for women over 50 OK for everyone actually.

Dress it down for Fall with a denim Jacket or add a classic cardigan for the office. Perfect for summer with a sneaker or Casual Fall Dress with a brogue or boot.

4. Floral Maxi Dress with Pockets

This J Crew Maxi (been in my closet a while) always makes me feel amazing. A classic silhouette and pockets. Yes, pockets in Dresses is a theme for me. I have worn this out to the vineyard, to the office and yes even to a wedding. A great dress can take you anywhere. The cami straps are traditionally summer, but a light cardigan takes me through the early days of Fall.

5. Old Navy Casual Shift Dress for women over 50

This sleeveless shift dress is perfect for the hot days of Summer but add a cardigan and fun shoe and you are Fall appropriate. I added a pair of fun leather converse to take me through the season.

LBD / Puma Sneaker/ Yellow cross body

6. The Perfect Casual LBD for Women over 50

They say that every woman needs a LBD in her wardrobe, well I say you need several. A Little Black Dress can take you through any occasion but depending on the style and material it may not be as seasonal appropriate. This fun dress found on Amazon has taken me through every season. Add a sneaker and I am ready for adventures, add a loafer or heel and I am ready for the office or a fun evening out.

Although truth be told I would wear my sneakers on a date or to the office because that is how I roll lately. Comfort is key.

Similar Old Navy Dress / similar sneaker in white

7. Long Sleeve Black Old Navy Dress

LBD’s come in so many shapes and sizes that I wanted to include a less body conscious style for some of us who are more modest. This fun dress has an eyelet scalloped hem and a fun tie neckline that can be adjusted to preference. Today I added a fun sneaker with zippers. Stylish yet comfortable. Anyone else gravitate towards a flat shoe/loafer or sneaker more than a heel lately?

Smash and Tess Cinnamon Jilly Dress (Similar from Smash and Tess) / Tall White Boots

8. Smash and Tess Cinnamon Dress

My current Smash and Tess was last Falls Jillian Harris Collab, not currently available. BUT don’t despair they have a current version in the same material and colour but with pockets. The Prosper Mini Dress in Cinnamon Brown is still available.

This beauty takes me from cool summer days into cooler Fall days. Summer I wear it with a sneaker or loafer and Fall works with a tall boot/cowboy boot or Bootie your choice.

Chambray Dress ( Similar Maxi Version) / Lug Sole Boot

9. Joe Fresh Casual Dress with Pockets for Women Over 50

Sadly this dress is no longer available and that makes me sad ( Maxi Version on Amazon) . This long Sleeve Chambray Dress always makes me feel pretty. It is lightweight so great for Summer but add a fun boot and leggings or jacket and you can head into Fall. It has pockets and the neckline can be open or closed your choice. I found this one at Joe Fresh and am hoping they bring it back in other colours.

Today I paired it with a fun lug sole boot from Shoe Dazzle that is still available in white, black or pink. And the VIP pricing on this boot is currently $11.24 so run don’t walk to the check out line.

Do You Transition Your Casual Dresses

So 9 fun Summer Dresses that I am currently transitioning to Fall. Do you completely put your summer pieces away or do you try and transition them into Fall?

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