Can I Wear Combat Boots After 40?

Hi Deb,

Is it acceptable for a woman over 40 to wear the combat boots which are popular again? I see a lot of young girls wearing them with short shorts but I’m not sure what a woman my age would wear them with.

Can you tell me the proper way to wear them? I remember wearing them in the 90’s and loved  how comfortable they were, but I have a feeling that these boots aren’t worn in the same manner this time around.  Please advise.  Thanks!  Trudy

how to wear combat boots


Hi Trudy,

Here’s a great example of an old trend that comes around and makes you wonder if you should try it again. I’m afraid there is no short “yes” or “no”  answer to this.

Combat boots work for some mature women. They look hip and cool wearing them because they have “the whole look.”  In other words they have paired combat boots with something unexpected and feminine like this leopard print scarf above. Combat boots have been spotted on stars like Diane Keaton and Susan Sarandon who wore them with a graphic print dress.
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Mimimum Effort, Maximum Style – Casual Dressing Made Easy

Casual Dressing for over 40 womenDear Deborah ,

I am a 49-year-old woman who lives in the Northeast, and while I do dress up occasionally for a dinner or evening out, 95% of the time I need to be dressed for getting in and out of a car, easily; for walking to and from places on a variety of sidewalks, and for a very casual everyday kind of life.

I’m finding myself at a perimenopausal standstill!  I have run out of creativity and I am sliding down the slippery slope of jeans, colorful t-shirts, fleece and turtlenecks.  Yuck!

I also have to wear comfortable shoes and boots to fit my aging feet.  How do women like myself, who live casual lifestyles full of activity and creativity, help ourselves to feel, and look, attractive, year round?


Thank you again,

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Confused about What Hose to Wear With Boots?

Lisa Ling in black tights and booties

Lisa Ling in black tights & black booties. (photo: shutterstock)

Dear Deb,

Do I match my tights to the color of my boots or to the outfit? In my mind if I’m wearing a skirt that hits above my knee I would wear a tight that matches my boot that hits mid-calf.

Also, what if I am wearing an ankle boot with a skirt or dress? Does the same rule apply? Thanks, Jennifer


Hi Jennifer,

1) Yes, do match your tights to the color of your boots not the outfit.
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Finding Mature Models is Challenging

Hi Deborah,

If you are an over 40 site, why do you use such young models?

mature female models

Mature female models

Hi Wendy,

I get this question all the time and I am  frustrated too… you see to there are just no photos of “real women” out there in current clothes that you can buy! I want to be able to show you things that you can go out and buy, but all the stores insists on using ultra young and super skinny models!

A few years back, I was excited to start working with a NYC modeling agency for women over 40, but they went out of business!

That is why I try to find women on the street photos, but it can be frustrating for our readers, since most of the time the outfits the women are wearing was purchased a last season and can’t be found now. [Read more…]

What Are The Rules For Co-ordinating Your Purse And Shoes?

Hi Deb,

It seems to be the style to not have your shoes and purse match. What and how do you determine what to match them with? The old way was to have black, brown, navy, or red if you were feeling wild and they always matched your purse. Can you give some pointers on what is in now? –~Barbara P.

Susan Tabac

Deciding what purse to go with your shoes can be tricky. Some women buy only one purse and wear it with everything. Others collect purses and change them around all the time.

It all depends on your needs and lifestyle, but, in general, your purse needs to be of high quality and the size should fit your style and personality.

This is a photo of fellow blogger Susan Tabak who always has great fashion sense!
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Can I Wear This To My Class Reunion (Part 2)

gray dress with black sweater coat

Kathryn sent in this photo and asked, “Does this look good on me?”

My reader Kathryn recently wrote to ask what to wear to an informal class reunion to be held at the local pub, in the dead of winter.

The grey and black layered/ belted look shows Kathryn is up on her fashion trends, however I felt it wasn’t very flattering on her cute figure.

I sent her some suggestions and here is what she came back with after looking in her closet.
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Do Pantyhose Make You Look Old?

Hi  Deborah,

Don't wear hose with sandles

Pantyhose with sandals looks dated.

I’d love to know what you think about the tights/pantyhose/knee high dilemma. When is a woman too old to wear tights, as in black, opaque tights or colored opaque tights?  If she is too old for tights, do you recommend pantyhose? 

Also, what about knee highs with pants?  If a woman feels that she needs them is it best to go with more of a “trouser sock” in black or a color, or to wear nude knee highs? Thanks, Michele

Hi Michele,

This is one of those “grey” areas that doesn’t get much press!  Since summer is coming, it’s even more relevant, so here’s what I think:

I do feel pantyhose can be aging but let’s be real, they are often necessary! The key to pulling them off is to wear an ultrasheer that is a nude shade that closely matches the color of your skin. Donna Karan makes some excellent sheer nude shades. If you are in between shades, choose the darker, but really nude should look “nude”.

A great alternative is a nude colored fishnet. These look terrific. Wolford makes a great one.

One final point, never wear pantyhose with a strappy sandal or mule! [Read more…]