It’s difficult to find that middle ground when you want to look fashionable, yet still feel relaxed. Here are our suggestions.
1. Wear a Dress with Leggings
Short flowing mini dresses worn with bare legs and heels look great on twenty and thirty year olds, but that doesn’t mean they are off limits to us ladies over 40. Many of these dresses look an awful lot like long tops, and so they look fantastic on if you pair them with dark leggings and ballerina slippers, or flat boots. Now before you cross your arms and say, “That’s not me”, give it a try. This is a chic and very comfortable look and once you try it, you’ll be hooked. Here are two examples of dresses that would look great with leggings.
This olive green peasant dress would look fabulous with brown leggings and a brown suede flat boot.

This black sweater dress is also a great option. Sweater dresses come in all fabrics, wool or cashmere, and are super cozy. We’d pair this with a big chunky necklace, opaque stockings and a fun pair of flats.

Finally, here’s Janine…JoJami’s sister in the complete dress/leggings/flats look!
2. Add a Wide Belt to your Outfit
The quickest way to go from boring to brilliant is to add a wide belt to your casual weekend outfit. A wide belt at the waist, or slung down lower on your hip, will instantly add a touch of the wow factor, kicking casual up a few notches. Our favorite belt designer (and you’ve heard us say this before) is Suzi Roher.
Roher belts can be found at high-end department stores and small boutiques. What’s so special about them? They stretch! This makes them super versatile. This is a belt that you will have to grit your teeth and buy, as it is on the expensive side; but once you do, you’ll find that it will transform your wardrobe and you’ll wonder what you had been doing before you had one!
See how this beautiful Suzi Roher belt makes this all black outfit look so much hipper and classier, while still looking relaxed? And, don’t you just love how it camouflages the tummy so well?
On a budget, but looking for something similar? Here’s another great stretch belt that does wonders to create an hour glass figure. One note here, if you are very short waisted then you’ll want to go with a slightly narrower belt, or you’ll end up looking like you are all belt.

This brown sash belt is also easy to wear. You can adjust it so it makes a “V” in the front, which is always figure flattering.

3. Splurge on a Sweater Wrap
Transitioning into Fall has never been easier or more fun, than owning a sweater wrap. Just putting it on will make you feel like you have more flare and sophistication. Sometimes the wrap is just something bright and cozy to toss around you like this Sayami cashmere wrap shawl.

Other times it’s part of a sweater set that cascades down the front like this Sutton Studio metallic tank set, and the Jones New York long sleeve cascade front cardigan on the right.
Sometimes it is more like a poncho. Anyway, it is a powerful and sexy way of wrapping up! When worn with a pair of jeans, a sweater wrap adds chic, grown up style to a very casual look.

4. Find some Fun Flat Shoes
If you love to wear your jeans on the weekend, update them with a great pair of flats. Check out these simple pairs of Arche flats for women. These are so comfortable you’ll never want to take them off.

Don’t they look great with JoJami’s skirt and dark brown hose? Want to look more playful? Try this look with a snakeskin flat!

5. Top it off with a Hat
Weekends bring a welcome change from having to do our hair. What better way to step out with bad hair and still feel great than to hide it under a stylish cap! This year men’s wear is big.
We were recently in NYC and saw the Fedora everywhere!Here is a simple black Fedora hat from DKNY.

We also love this French Beret from Nordstroms. With a great scarf and t-shirt and jeans you will have some fun with this nod to French chic. The black wool beret will also look very nice with your jeans.

Hi Deb and JJ,
I’m currently recovering from knee surgery and am facing another surgery due to my rare knee condition. Since I’m been laid up for almost 2 years I’ve lost track of how to dress appropriately even just for casual wear. I’m 47 years old with an hourglass figure. I wear a Canadian size 8 – 10. Since my job was working with kids with physical disabilities I liked to dress casual but still look chic and professional. I need to learn how to dress casual chic when going to physio, Doc appointments and just out in the community instead of wearing athletic clothing.
~M.T.
Hi M.T.! We know that we all love and need to be comfortable, but we want to assure you that comfortable can still look great! We are going to assume that high heels probably won’t be an option for you, but you’re in luck, since the biggest trend this fall is the flat boot.
We suggest that the first thing you do to update your wardrobe is to throw out anything that you feel is not making you feel like you look great. Once your closet is organized and looking a little barren, then you are ready to fill it back up with some new updated items! (For help organizing your closet, check out our DVD, The Ultimate Cure for the Disorganized Closet!)
First off, for a professional office look, try some pants in a micro fiber. These never need ironing, and have some stretch in them for a slimming, super comfy fit.
Next, find a great blazer that will either match or coordinate with the pants. We want to make sure you show off your great waist, so opt for one that has some darts in it, that is a shorter style and fits well.
Another option for the run around days is a comfy skirt with flat boots, and a nice fitting cashmere sweater or vest. If you wear jeans, just make sure that you buy a new pair that is updated and in style. You will want to opt for one with some flair to balance your figure out. Also, do not be tempted to tuck in! Just make sure that your top is fitted and throw that new great fitting blazer on top.
Do not wear tennis shoes with this. Go for the flat or short boots with a wedge, or even a low heel. Don’t forget to update your make up and lipstick!
We came across a great thing over at Nordstrom’s… They have something called The Top 10 where they list the top 10 fashion trends and then you can shop the trend. We have done all the work for you…
Here are our top 5 trends out of the of the 10 including what we would buy and why. Have some fun, check out the site and comment below. We’d like to hear what you would choose!
1.The Stand Out Coat: Everyone needs one. In the fall and winter you will wear it almost daily. Here is one we like. It’s a modern pattern and color combination, but the cut is classic.
2. The Pencil Skirt: A pencil skirt should be simple and fit well. We liked this one the best, especially the way the hem falls at just the right part of the leg.
3.The Statement Necklace: We strongly agree that a statement necklace is a must have in your wardrobe. The neck is one of the areas on a woman that stays sexy the longest. Let’s celebrate it with sparkle!/p>
4. The Short Jacket:
Its hard to see it in this photo, but this jacket has a lot of detail to it. The sleeve has just a bit of flair at the cuff. We like the overall fit too!
5. The Bootie: This was a hard choice, but this one is a great price and has lots of class.
1. A Sexy Bra
Granted, after 40 your breasts are typically heading south, but that doesn’t mean you should cover them up with a boring, stretched out beige bra up and forget about them. The quickest way to feel good about your changing boomer body is to Perk up your girls with a gorgeous, sexy new bra. Splurge on something a little more feminine and pretty. We are seeing some gorgeous options out there like two toned bras in ice cream colors of lime sorbet and lemon ice, rich chocolates and strawberry pinks! Or for the holidays go bold with jewel tones of ruby, amethyst or emerald. How fun to run around all day knowing that underneath it all is a sexy woman!
2. A Cape
The trick to looking fabulous after 40 is not to try and look young, but to look modern. A cape is a great way to do that. Fashionable and fresh, a cape is a sophisticated way to show you’ve still got flair! Not only that, but they are really comfortable, since they are not as restrictive as a coat and warmer than a pashmina. It’s the newest look in stepping out in style! Go for a grey or deep chocolate color for a versatile look that can go day into evening. If you go off to a black tie affair, of course a black velvet one can be quiet gorgeous and very formal.
3. Sleek High Heeled Boots
A simple formula to look boomer chic is to stick to simple classic looks, (a crisp shirt, flat front pants and fitted cropped jacket, for example) and put the emphasis on the accessories. One of the most important details this season is boots. Finding a wow pair to personalize your look is key. Nothing can date you faster than an out of style, worn our pair.
Opt for a boot that is finer in style to ooze sophistication. Not too round or square toe and keep the heel thinner or go for a wedge. Too clunky is funky and better left to the younger crowd! If you’re looking for comfort and style, try some of Cole Haans new boots that have Nike air cushions in the toe. As we age, our feet get drier and the pad on the bottom of the foot can become tender after walking all day. This pair allows you to have fun in heels and still feel comfortable.
4. Smart Handbag
Enough of teensy weensy bags that barely hold your lipstick and ridiculously oversized purses that let you lug around everything you own and make you look like a bag lady. For Grown-Up gals it’s time for something stylish but smart. There’s a whole new line of luxury bags out there that look gorgeous but also keep you organized. We think the Butler Bag is a great choice because it is fashionable on the outside, but the inside stays absolutely organized!! The new exotic fall colors in spicy ginger and olive martini are just the thing to add some zing into your wardrobe!
5. Gorgeous Gloves
If your coat is neutral and you want to jazz things up, try a new pair of fresh gloves. Snakeskin and extra long leather is all the rage this season. Bold colors and exotic skins are easy to pull off, especially if you’re only wearing them until you step inside. Look for soft supple leathers that aren’t too bulky. Sure you have the ones you walk the dog with but for going out change them out. Don’t go for the practical black or brown ones; find something that sings your personality. Dare to be wild. You will have fun soaking in all the compliments!
How many times have you wandered around a store, finally found something you kind of liked, but ended up frustrated asking yourself, Is this to old? Is this too young? What’s just right????
Is there such a thing as age appropriate and how the heck do you know when you find it? The truth is that while dressing after 40 depends partly on your body and partly on your attitude, there are some basic style guidelines you can rely on to make you look modern and fresh. Take a look at these 3 examples.
JEANS
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Too Old
The reason jeans have remained a staple in womens’ wardrobes for so many years is that the right pair can make your body look goddess-like.
But not this pair! They’re stiff, boring and unfeminine. The high waist sits up past the belly button. Instead of complimenting your curves, high waisted jeans will emphasize your tummy and behind, making you look very big and round. To boot, these jean narrow at the leg making the hips look larger. Also the length of the jean is all wrong, exposing your shoes and making you look shorter and heavier. Donate these to some farm hand. |
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Too Young
Skinny, tight, low cut and flashy. Let’s be honest. These jeans are designed for a tight Little twenty-something body. Sure if you have long thin legs and you wear a big belted top that covers your bum over top of these jeans you might be able to get away with this. But for the majority of women over 40 who Carry a Little extra weight, these jeans will make you look like a stuffed sausage on heels.
Also, don’t know if you can see that this particular pair features faded kitty cat whisker lines across the crotch area. Meow!… another good reason to stay away from these if you are over 40. The whisker lines will only draw attention to your lower stomach and by trying too hard to be trendy you’ll end up looking tarty. |

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Just Right
The right choice of jeans is something sophisticated and modern. We like these classy jeans with a medium rise that lands just a tad below the belly button because they are really flattering to so many body types. These jeans are clean and simple without fussy distracting details (like cat whiskers! or glitter or embroidery, which by the way ladies, is now out of style) A dark blue wash like this always looks rich and also makes you look skinnier-bonus!
See how the wider flare at the bottom balances out the hips beautifully and the pants length comes right to the shoe. Also, make sure your jeans have some stretch to them, like these do. A little Lycra goes a long way to help get the perfect fit. |
TURTLENECK SWEATER
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Too Old
Oh come on let’s all admit it. You’ve probably owned one of these at some point and maybe even still have one hanging around in your closet somewhere. It’s the classic turtleneck we all grew up with. Beware, because this very conservative style just shouts “Old lady”. The color could work if it were another sweater but the cable knit pattern, stiff high neck, looseness at the waist and shorter sweater length all add up to a much needed trip to the Salvation Army. |
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Too Young
Yes it’s new, yes it’s modern but it’s also a great way to add twenty pounds. The problem with this top, is that first of all the short sleeves are hard to pull off after 40. There’s all that jiggly stuff going on when you lift your arm up, right? Don’t want to play that up, do you? Plus, cute cute baby doll sleeves do not make an older woman look cute. They make her look like an older woman who is dressing babyish.
Thick, chunky knits like this add bulk for sure, and make you look heavier. Finally the bell shape of the sweater, might make you feel like your hiding that tummy, but in reality it will draw everyone’s eye to this detail, and therefore your pooch. Need any more reasons to stay clear of sweaters like this one? |
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Just Right
This beautiful black turtleneck has a very relaxed classy feel. The cotton modal fabric is lightweight, comfortable and smooth. The neck is still high but softer and the whole top is fitted just enough to skim the body and give a womanly shape.
The length is great because it hits the hipbone,covering up any gap between pant and stomach and it camouflages the tummy. You will never go wrong with a high quality black turtleneck like this. |
BOOTS
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Too Old
If you really are serious about looking chic and updated, you will not want to be seen in a boot like this. Sure it’s practical, but really ladies: Life is too short to be Frumpy. We’re sure you can find so meting with just a little more personality. Stop settling and buy something you really love. |
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Too Young
The magazines may be saying that these rusched boots are current fashion rage, but after 40 it’s your job to take a Style stance and just say no to fussy trends like this. These boots are too busy and funky for gals our age. Think of it this way- they’re scrunchy and wrinkly so they are going to emphasize the other parts of you that are scrunchy and wrinkly. Do you want to look like an old Boot? |
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Just Right
This snakeskin boot has just what it takes to look classy with a bit of fun. The heel is just high enough to make you feel sexy but not so high where you feel that you might topple over minutes after you put them on. They’re elegant and modern, but subtle. Subtle is the key. |
One final tip about Boots: Invest in a quality pair of boots. It shows! If you take proper care of them, they should last 3 or more seasons. Make sure to spray them with a good leather or suede sealer when you first get them, and reapply often. Don’t forget to touch up the toes! Nothing worse than great boots where the color has worn out at the toe.
Fall’s new boots have arrived, and they are marching across town into your favourtie stores and hopefully into your closets.
But the big question we’re getting is What do you wear with them to look stylish and hip?
Let’s start with what Deborah calls “Power Booties”, shorter style overgrown pumps. These have a collar added on.

These are a lot of fun, and can really make you look like a style diva, when worn with a fresh pair of opaque tights and a more tailored look. Power booties add va voom to conservative outfits, like this. Of course you can always wear them with pants too, but then no one will see them, so whats the use of that? So, we suggest you take a very simple dress like this knit from Anne Klein (available at Nordstroms), add tights and booties and viola!, it’s a hipper new way to dress things up.

Next, on our list of new favourites is the flat riding boot.

We love this look, because most importantly it is comfortable. There’s many variations to choose from ranging from outdoor rugged to city sleek. Riding boots look best worn tucked into straight legged jeans, with a full skirt, or sweater dress.

There’s a cute pair that can double as a rainboot, at Tory Burch.

Finally,the stretch boot, back again this year, is our all time favorite investment. Nothing feels sexier too because these babies which literally fit like a glove.

The stretch boot looks best with sleek sophitcated styles, in ther words, fine knits and clean lines vrs. bulky sweaters, and heavy, busy fabrics. Here’s one with a wedge, which is super comfy, but not quite as sexy as ones with a heel.
