How to wear a maxi dress for women over 50

Jun 15, 2016

Last Friday lent itself well for running errands. It was sunny and warm but cool air was still dominant. And I was too lazy to shave my legs. In addition, I didn’t feel like wearing jeans or pants.  Basically, I just wanted to be wallowing in extreme comfort.

And so, with spring looming overhead, I threw on a grey maxi dress that I bought on sale last year. I love this dress because the cut is both different and flattering. It’s sleeveless, has a high neck and a waistline that falls just below empire.

Loft Lou and gray maxi without jacket

My apologies for the quality of the pictures. I buckled and tied the belt at the high waistline and bunched the fabric slightly so that I could wear flat sandals. My hips are big–and the narrow cut of the dress is actually more flattering than a wider fit would be. 

This warm day made it better to further break in my sandals from last summer. I wore my denim jacket and was off.

I thought the outfit gave off a nice relaxed vibe. I looked good and I felt good. When you wear clothes that make you feel good, your attitude is always great!

Loft Lou & Gray maxi denim jacket belt and rondini sandals

I had to post a small pic because the photo is really out of focus. Sorry! But here’s how the dress looks with the denim jacket. A longer jacket or coat would have given a dowdy look. The cropped length of the jacket is perfect!

One of my errands had me stopping at Old Navy to see if I could pick up a few more Perfect Fitted Tee shirts. (And that is another post which I will be ranting about in the future). As I exited my car and walked from the parking lot to the store, I noticed two younger women looking at me. My reaction was “Oh shit, what ripped?”

As I got closer to the store, they approached me to tell me that they loved the way I looked! I was floored! They continued to tell me that my dress, along with the denim jacket and sandals just looked fantastic. We continued talking for a couple of minutes. I told them where I made the purchases and they also complimented on my hair. My hair was looking good from Adam’s blow out a few days prior. When I told them that I was going to be 61 years old next month, they paid me the highest compliment. They said they want to look like me when they reach my age.

Let me tell you, I was so thankful to these women for such a great compliment. It made my day. It also made me realise something: kindness counts. We need to compliment more—especially those we don’t know.

And so I thought some more. But this time I thought about how carefully I put this outfit together—even though I wanted a casual and relaxed vibe, I still had to put come effort into achieving this look. And I achieved the look without looking like an older woman who was desperately trying to look young. My outfit did not come off as costumulicious (my made-up term for dressing as though you are wearing a costume)

Maxi dressing isn’t just for young women who want to stay on trend. Older women can wear a maxi if:

  • Keep it simple. Keep it light. Don’t overload on accessories!
  • Pay attention to proportions. Cropped jackets and sweaters work well with longer length dresses.
  • Mind your fabrics. You want a fabric that drapes and flows nicely.
  • Fit counts.
  • Wear appropriate footwear. Sandals are perfect!

Anyway, come on with me and I’ll show you what I mean. We’ll have fun and stay within an affordable budget.

Below is a maxi dress by Cynthia Rowley. I purchased this last year for $29.99.

This dress is “maxi long” which means, if you wear flats, you will be tripping over your feet and the hem will become filthy in a very short time. With a maxi this length, a heeled sandal looks better.   This is a dress that could be worn to a fancy dinner—it isn’t the most casual of maxis but it isn’t formal either. To dress it down, I would wear a larger scarf at the neckline.

Cynthia Rowley maxi full view

This dress is made of 82% Rayon and 8% Spandex, giving it a nice drape and fit. It is unlined but the fabric is incredibly opaque. The shoes are Calvin Klein sandals. These heels are so comfortable. The shoe has a stacked heel and navy elastic straps on the upper. 

I make no apologies for my turkey neck. Screw it. It’s part of me. Gobble. Gobble.Gobble…

Cynthia Rowley maxi with Lilly Pulitzer for Target scarf

If you want to hide turkey neck or a crepey cleavage, a lightweight scarf will do it. The lighter fabric lends itself well to warmer weather. This is a “Lilly for Target” scarf I purchased last year. The lighter blues and pink are a nice contrast to the darker dress.

NOTE: I didn’t accessorise any of the outfits that I’m wearing except for scarves. Why? It’s because I wanted to concentrate on the fit and look of the clothing. What I AM OCD about is the correct footwear for wearing a maxi. Flat sandals, heeled sandals and strappy wedges are the perfect footwear for maxi dressing. In my opinion, a closed shoe ruins the relaxed look. 

Next is my favourite maxi. This grey sleeveless maxi from Old Navy. It retails for $29.94 but I purchased it for 40% off. I love this dress so much that I purchased two in grey and one in black. This is the perfect maxi! The cut is very flattering. I’ve got some high neck love working here and the neckline also protects against the sun hitting the chest area. The cut of the arm holes isn’t so deep either – giving the dress an even better fit. This dress is also very forgiving for those of us who may have gained a few pounds in the middle due to menopause and age. The dress also has darts at the bustline! DARTS! I haven’t seen darts on a knit in a long time!

Old Navy gray sleeveless maxi without jacket.

See how simple this dress is? Old Navy strikes a winner with this one. I purchased multiples because–just my luck–it’ll be discontinued!

Pld navy black t shirt maxi with tropeziennes

Here’s the same dress in black. The shorter length means flat sandals! I paired this with a wider belt sitting at the hips. It makes my torso look longer! The fabric is 70% Modal and 30% Polyester. However the fabric does breathe. Made in Indonesia, the dress is also very well-constructed. Oh–and the knit is tight–nice and opaque. Not flimsy at all!


This dress is “maxi short”. You won’t be tripping over the hem. Because of the shorter length, this is perfect for wearing very flat sandals or flip flops. If you want to dress it up a bit, you can wear a lightweight scarf or a cropped sweater. Speaking of cropped sweaters, if you aren’t too fond of your upper arms, this is a great way to disguise the upper under arm flaps.

Old Navy t maxi with better view of cropped sweater

Cropped sweater – got it for less than twenty bucks. 78% Rayon, 22% Nylon. It is tightly knit so it’ll keep shape nicely.

I’ll tell you though: at my age, I don’t even care how flabby my arms are. I’m wearing this dress anyway.  This is a great vacation dress as well. Wear it to the beach, then wear it touring and out to dinner. With a dress like this, you can pack less!

Old Navy gray sleeveless maxi neckline detail and sloan bag and tropeziennes

To finish off this look I pulled out my Kooba Sloane bag from my closet. I like the way the bag complements the sandals! Both bag and sandals are years old!

For the mature woman who doesn’t want to go completely sleeveless, this 3/4 sleeve length maxi is a good choice. This was purchased last year and I’ve gotten a lot of wear out of it. Between childbirth, maybe not exercising as much, and middle-aged spread many of us don’t have the bodies we once had. And it’s OK. You can still wear these dresses. In fact, I like the way they hide my cellulite ridden thighs. If you have a lazy day or three you don’t have to shave the legs. Hell, you can go commando if you want because you don’t have to worry about bending over and displaying your origin of the world! It’s your choice!

Gap Rugby striped 3.4 sleeve maxi with boatneck and shoes

I like the way this dress is draped. The stripes may make me look a bit wider in the waist area, but I really don’t care. I love the ballet/scooped neckline too. Screw the turkey neck. If I like the dress, I’m wearing it. Embrace the neck! On my feet are Old Navy flip flops from the year of the flood. They are incredibly comfortable too!

Back to Old Navy and back to Rugby Stripes. This berry and blue is last year’s model. It’s a longer maxi and I paired it with Crown Vintage wedges from quite a few years ago.

Old Navy berry and blue sleeveless maxi and wedges

In cooler weather or in heavy A/C I would wear a lightweight, cropped denim jacket with this dress.

Maxi skirts? Remember that proportion is just as important! I ordered this maxi skirt from J. Crew last year. I’ll be honest: it isn’t my favourite because the cut is a wider A-line and it feels like an overabundance of fabric. The skirt is composed of 95% Viscose and 5% Elastane (a type of Spandex). But when wearing a maxi skirt, I think it’s very important to make sure the top you are wearing is fitted. The fitted shirt will flatter the overall look because it won’t look sloppy or frumpy.

Below looks good…

Gray Maxi J. Crew with Merona 3.4 sleeve boatneck

I may not be crazy about the skirt, but it looks pretty good with this fitted knit shirt by Merona. 95% Cotton (horray!) 5% Spandex. 3/4 sleeves. A bargain for ten bucks at Target. BTW. SIZE DOWN for a very fitted look. Knit shirts have a tendency to stretch out. Sizing down will ensure a great fit after many wears and washings!  

Below is NOT a good look. The shirt is too loose-fitting and the relaxed fit is sloppy. Trust me, I don’t give a shit HOW big my ass is or how wide my hips are but I’ll size down for a great fit in a tee or knit shirt!

Gray J. Crew A Line Maxi with relaxed t. No wear

Yeah–the photo sucks but take a close look at the tee. It’s just too loose in the shoulders and too loose in the middle. This shirt IS a relaxed fit tee from Old Navy. I sized down to S and will only wear it with skinny jeans. At five bucks I couldn’t resist the “Cote d’ Azur” theme!

Below is another maxi skirt. I like this one a lot because the cut is narrow and the slits on the sides make it easy for brisk walking or running away from someone you don’t want to see! This skirt is from Old Navy. I’ll tell you–denim jackets are NOT just for the younger crowd.  Denim jackets + older women = One Great Look!

Last look is a Gap skirt I purchased last year on clearance for $9.99. The skirt was advertised as “maxi” but is really a cross between maxi and midi. I’m surprised at how much I love this skirt! It is 100% cotton! The knit is heavier and drapes very nicely. For a skirt with no stretch, this really keeps its shape. It is perfect for this time of year. I would not wear this skirt in the middle of summer due to the weight–but I would actually wear it in winter with high boots!

Gap midi maxi with denim jacket

I’m wearing this with an Ann Taylor stripped boatneck knit top. 3/4 sleeves. The shirt is 60% cotton and 40% Modal. Here’s where trying clothing on before purchasing is important. This shirt is a Medium and is very snug. 

More stuff for the old ladies to know:

Don’t hesitate to play around when trying clothing on. I purchased the maxi dress below from Loft last year. I loved the dress but HATED the way the front looked on me…

Loft 95 rayon 5 spandex front of dress ewwww

For obvious reasons, this dress looked like shit on me. Saggy titties do not look pretty! But because I loved the print and the flow of the dress….

Lopft 95 Rayon 5 spandex backwards

I turned it backwards and LOVED the way it looked. I wear this dress when Bonaparte and I go out to dinner during the hot summer months. It looks so much better worn backwards! Especially for us older women. The bustline is more flattering! You don’t even need to wear a bra either!

Shoes like these look great for maxi dressing!

Sandal scandal

Don’t forget the bags either. An unstructured bag is much better for this casual way of dressing. Save the structured and lady-like bags for the office or special occasions!

Maximum handbags

I would also like to add that every outfit was purchased on sale. As many older women are on fixed incomes, it’s important to point out that you do NOT have to spend a fortune to look good when you are older. We old ladies need to show the world that we can rock any look just as well, if not better, than younger women!

We older women are just like everyone else! Age has no limits!

Old Navy berry and blue with denim jacket

We can have a relaxed vibe and can look great at 50, 60, 70, 80 and up to over a hundred years old! Don’t forget to mess the hair up a bit!

Here’s to all the older women of the world!

Originally published here

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