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? 

If so, what would be the proper way to wear them? I remember wearing them in the 90′s and 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

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.

the signs are everywhere.

the signs are everywhere. by kirakay featuring enamel rings

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 feminine like the outfit above.

If you try to wear combat boots with an army fatigue look or with all black with leather, you a going to look like you are wearing a military or old rocker costume. It’s the contrast of the feminine and the masculine that you need to pull off this look.

It’s not a look I will be investing in. My taste leans more to a boot that looks sleek, clean and simple. There are plenty of comfortable boots that are in style other than this trendy look. I have actually tried on a few pairs (some more radical than others) and felt that they would just not fit into most of my wardrobe.

None-the-less, if it works for you, go for it. Dressing after 40, or at any age is all about personal expression and being authentic.

Would you wear this look? Comment below and let me know your feelings!!

Are Wide Capris Pants out of Style?

Hello Deborah,

I am leaving for Florida next week and would like to know what’s the verdict on the wider-leg capri pants we were all wearing last summer. I see that wider (long) pants are in, but I not sure about the one that hit above the ankle.

I have several pairs in flattering black crepe; they were a staple last year, and so easy/comfortable to wear. I do like the straight leg, snug fitting Capris — but do I have to put my wider ones away this year?

Thank you, Cindy

These types of capris are out of style, too short and the cuff is a no no.

These types of capris are out of style, too short and the cuff is a no no.


Great to hear from you! Your question is a good one.

I recently wrote a post about  the new version of the Capri and it is definitely different than last year’s, however if your old Capris are still in good shape you should feel fine wearing them.

Just don’t buy anymore like them on your next shopping trip!

If you still want to wear them, try updating them by wearing one of the new clunky wedges.




Mother Of The Bride Needs Some Help…

Dear Deb,

I am on a very tight budget due and my daughter is marrying next June. In my closet I have is the pretty simple silk long A line skirt with matching jacket that has only been worn once. I am thinking of having the jacket tailored more (it is too boxy) and wearing it with something else  for a bridal tea or dressy evening out. Unless you have a different idea for me, the wedding will be during the evening and the temps will be warm in Alabama.

Can you take apart this matched outfit?

Can you take apart this matched outfit?

Here is a little about me:   I am 52, 5’3” full busted, broad shoulders, short waist, not extra heavy, but pudgy.  My hair style is wispy short with salt and pepper throughout. I really like sparkly things, chunky jewelry, scarves & wraps.  People seem to compliment me when I wear winter colors.   I do not want the normal mother of the bride look, it dates a person I think; I want to look happy and radiant for this most special occasion. Help me think of what I could do to look good for my girl and feel comfortable for the evening. Thank you, Karen H, Montgomery, AL

Hi Karen,

I  understand you wanting to update this dress, however we have another idea for you.

I really like the outfit and the color works perfectly with your cool skin and hair.

The skirt looks great so we think you should still wear the matching jacket but have it tailored so that it  fits you nicely. (Someone on my facebook page, suggested you might change out the buttons! )

This outfit is classy with out being fussy and as long as the jacket fits well you will look gorgeous. Also, the “v’” neckline of this jacket will probably be more flattering on you than the simple scoop necked top. ( Also since the jacket has a collar with your short hair will flatter you in photos!)

You can add a wonderful chunky statement necklace to it, like you mentioned; if you can find one that is more in a “v” shape it will look best.

You may also want to have the skirt shorted to right below the knee and  still wear the matching jacket, nude hose and some gorgeous pumps (peep toe or regular).

When you try to mix and match “matched” sets, it can be very tricky to pull off.

In the photo below, trying to pair the elegant skirt it with a casual top just doesn’t look right.   (Your sweet puppies look concerned too!)

If you are stapped for cash check out this new site: Recycled Brides. They have gently used MOB dresses!

It is very hard to make a “new” updated outfit with a classic skirt like this.

Anyone else out there have other ideas? Feel free to comment below!

Need help with your upcoming event? Check out my e-book, Tweak Your Chic,How to Dress the Mother of the Bride.


What About Casual Dressing after 40?

woman over 40 in red turtleneckDear 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, Lori

Hi Lori,

Your letter was so heartfelt and your question so common! Many women see their lifestyle change once they are past 40. Casual wear becomes something they wear a lot! Here are a few tips to get you started:

1. Do you have a Cute Vest?

Many women don’t think about buying a vest to dress up their casual wardrobe but I bet if you do you will be hooked. Vests like this leather and faux fur one are very popular at the moment and look great at any age.

Wear one with jeans, a shirt and some real cute books and you have a showstopper casual outfit.

faux fur vest

Wear your vest with jeans and funky boots for a hip look.

2. Have you tried a Sweater Dress?

and some patterned tights and knee high or over the knee boots!  Don’t feel like you have to wear pants all time. Why not snuggle into a sweater dress and feel more feminine and a little more funky!


3. Try a Dash of Color

Lord knows we wear far too much black after 40 and it’s not always so flattering. All those years of black can really drag a woman down now that our skin is not as vibrant as it once was. Read all about ABD and you will know what I’m talking about.  It’s time to put some color into your casual wardrobe. A coat is a great place to start.

This type of casual coat gives a pop of color and still is comfortable.

4. Have you considered Leggings?

You say you want to be comfy. Stretchy leggings are the most comfortable thing you can wear. The key to looking good in them is to make sure they cover your bottom and more. Buy some thick black leggings and pair them with a long loose sweater like this. Add some jewelry and glam accessories and you have a chic casual look.

leggings over 40


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.


2) When wearing an ankle boot with a skirt or dress, it will look best if you do keep the tights the same color as the boot. (Notice how these boots from Nordstrom fit nicely around the ankle. Good fit, will make the short boot more flattering to the leg!) The fashion magazines are showing the young gals wearing all sorts of fun colorful tights with these short boots and if you are daring you could try that.

But for most of us, it is just more sophisticated to go solid, black or brown. P.S. Stay clear of sheer pantyhose with short or tall boots, they will look too fine and will not look right unless your outfit is on the dressy side.

Obviously the skirt is too short for 40+ but take a look at sheer hose with booties- this doesn’t work at any age!


Finding Mature Models is Challenging

Hi Deborah,

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

group of women over 40Hi 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? T he old way was to have back, brown, navy, or red if you where feeling wild and they always matched your purse. Can you give some pointers on what is in now? -~Barbara P.

Your purse and shoes do not have to match but they should blend in style and weight.

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!

See how the colors all blend and her purse does not stand out, but pulls her simple outfit together!

Here are a few basic rules to remember:


Play with mixing colors, but keep one color neutral :If you have gray shoes, you can have fun with a colorful bag. This look is more for work because of the stiffer, dressier bag. The slouchy bag in front  with the gladiator sandals are better for a casual look because they are both less formal.
An outfit made up of  solid colors will get a lift from a purse with some color or texture :
This simple outfit is perked up with these purple flats and a snakeskin clutch.
Don’t do a stiff purse with a casual outfit:If you like to wear casual or soft flowing clothes your handbag should match the look. This purse is too boxy and stiff for this sporty outfit.

This softer,relaxed hobo style purse is much better with this outfit~

Soft look with a soft style purse
Even a formal purse can work with casual  shoes.

This formal channel style bag works with these flats, since the flats are shiny and have a dressy look to them.
Coordinate your hardware: It will be  easier to make choices and you will feel more pulled together if you keep your shoes, jewelry and handbag hardware all the same finish. (e.g. silver jewelry, silver, buckles on shoes, silver zipper on purse)
3 bags 1 shoe

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 was not so flattering on her cute figure.

I sent her some suggestions and here is what she came back with.

checkered shirt and clunky shoes

Checkered shirt and clunky shoes

Kathryn sent in this outfit and asked if this would work. Even though it is an informal event, this outfit is way too casual, and dowdy if Kathryn wants to dress to impress! The layers hide all her curves, and the checkered shirt and clunky shoes make her look very masculine.

The long, light-colored top is the wrong proportion on the body, and makes her legs look very short in comparison. This is definitely not a look I would recommend.

It looks classy and crisp

It looks classy and crisp

This look is much nicer! It looks classy and crisp, and the shapes flatter her figure.The only point I’d make is that it’s just too conservative!  From the first outfit to this one,  Kathryn’s style has disappeared.  Where’s the hip touch we saw in the first outfit?

adds a little sexiness to the outfit

This adds a little sexiness to the outfit

This makes her figure look cute but is rather school girlish. She might be better to wear this dress without the blouse and throw a colorful fitted jacket on top.Adding a pop of color will give her outfit some visual interest, and help her stand out!

 winter white wool trench

Winter white wool trench

Kathryn also sent in a picture of her coat.  Isn’t it adorable?  I love the winter white wool trench with the cinched waist and decorative vintage pin.The A-line is a perfect cut for her too.  That just goes to show that even in sub zero weather, you can still look hot!

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 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 peep toe shoe or mule! [Read more...]