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How to Wear Combat Boots over 50

 

Today I am joining my friend Brenda from 1010 Park Place to chat about Combat Boots. I am sure this topic will be a hot one! I know you ladies will either love them or hate them. I have been searching for a suitable pair for a couple of years. I wanted a pair with a wide enough toebox (the darn bunion) but stream-lined looking. I found the perfect pair. I love them and they are comfy. Let’s talk about how to wear combat boots over 50, shall we?

How to Wear Combat Boots over 50 cindy hattersley and brenda coffee

Before Brenda and I show you how we would style them let’s talk about some of the fashionable ladies that rock them. They are a part of many celebrities’ uniforms. Diane Keaton is rarely seen without a trusty pair.

ageless style-diane keaton

Meg Ryan has rocked the bad girl/girl next door grunge look for most of her career.

 

meg ryan in combat boots

Jennifer Anniston always sports a tasteful version.

jennifer-anniston-in-combat-boots

Lynn Slater (former college professor) and pro-age fashionista loves her combat boots.

lynn slater icon accidental in combat boots

 

My suggestions if you are considering a pair. Purchase a pair that isn’t too over the top but has just enough kick to be fun. Style them in a modern way that is somewhat appropriate for your age. Play with the contrast of tough versus feminine just enough to make it a bit edgy.

Here I am wearing a chunky black funnel neck and boyfriend jeans. I think this is a comfy everyday look that isn’t too edgy.

 

cindy-hattersley-in-jeans-and-combat-boots

SHOP THE COMBAT BOOT LOOK

If you want to go outside the box a bit (why not, right?) You can easily toughen up an otherwise frilly outfit as I did here with this skirt and turtleneck combo. Necklace is by Paula Carvalho Designs.

cindy-hattersley-in-tulle-skirt-and-combat-boots

SHOP THE COMBAT BOOT LOOK

A retro poncho from Anthro with slimming black trousers creates a more tailored classic look.

SHOP THE COMBAT BOOT LOOK

If you like a slightly edgy look but don’t want to look like you are trying too hard, how about leather on faux leather and combat boots? Here I am wearing my favorite faux leather Spanx leggings, a simple black turtle from the gap, and a long leather jacket with my combat boots.

cindy hattersley in leather and combat boots

SHOP THE COMBAT BOOT LOOK

Last but not least, I am pairing my combat boots with this fabulous skirt I found in Florida from Nicole Paloma Designs. I kept seeing women in these skirts when we visited Rosemary Beach and kept thinking how clever the concept was. Nicole makes these in tons of fabrics and they are oh so fun and flattering (this is not sponsored she is a small business in Seaside Florida). Here I am with all my pals at Mary Ann’s birthday party here this week.

bloggers gathering at cindy hattersley's

Here is another shot of the skirt (without combat boots) so you can see the clever design. She leaves the seams frayed. I am crazy about this skirt. I love supporting small boutiques. She hand sews every garment and has a shop at the Hub30A.

cindy-hattersley-in-nicole-paloma-

So what do you think yay or nay? I know I could never pull off that super chunky lug sole look, my feet are too wide and big. I do love the ones I purchased ( the McKenzie from Stuart Weitzman). I bought mine on eBay where you can still find them, but I have linked similar ones. You might enjoy our Fashion Over 50 fall fashion post here. You will also enjoy this Youtube video Can You Wear Combat Boots Over 50. 

If you are looking for comfy stylish boots after 50 you might enjoy this post here.

If you are into Slow Fashion you might enjoy my post How to Wear One Blazer Eight Ways.

Thanks for reading How to Wear Combat Boots Over 50. It is time for you to weigh in and pop over and see how Brenda has styled them! Brenda took a year off to write her memoir, but if you aren’t following Brenda’s blog, I highly recommend it.

 

1010 Park Place

 

 

Reader Interactions

Comments

  1. Susan says

    You look cute in the boots! I had never considered them for myself until I randomly saw a photo of Kate Middleton wearing a See by Chloe lace up pair in dark brown suede (?) with a less clunky look. Sure wish I could find a similar pair! Think I’d wear them a lot ! However not sure they fit the “combat” definition, whatever that is!!

    • Cindy Hattersley says

      Hi Susan

      Who cares about definitions anyway? I noticed when I searched combat boots nearly every lace-up boot imaginable came up!!

  2. Linda Johnston says

    Has to laugh because I’ve been wondering if I should go to the trunk in our attic and get mine out from my Army days! Not quite as. stylish as the ones you shared but just might work. Love your skirt too.

  3. queenmum says

    I am what you call a minimalist. I like classic but stylish clothes. My Doc Martens are my go-to boots in the Fall and Winter casual wear. They are so comfortable, warm, waterproof and I’ve been wearing them for years.
    For those who aren’t sure about them, give them a try and see how much younger and more hip you feel in them.
    At our age, we can dress how we like!
    LOVE that grey skirt!

  4. LA CONTESSA says

    ABSOLUTELY NO!
    TOO MUCH WAR IN THE WORLD TO BE LOOKING AT MY FEET THINKING ABOUT COMBATTING!
    YOU ROCKED THE LOOK BUT I WOULD NEVER WEAR……….EVER.
    Heck I just bought my first PUFFER JACKET SO NEVER SAY NEVER!
    THEY LOOK INCREDIBLY UNCOMFORTABLE TO ME AS WELL BUT I GUESS OTHERWISE FROM THE COMMENTS!
    A GREAT SUBJECT FOR FASHION……………..its always been interesting to see what will the public RUN WITH.

  5. Liana says

    Mature skin make up is certainly a topic we can’t never know enough. I’m constantly searching, reading and gathering info and tips. My eyes are in major need of help. Being part Asian, I used to have monolid hooded eyes that after years of sun damaged are now overly hooded, snd the extra skin is enough to build an extra pair of eyes applying eyeshadow had become a crusty crispy cream donut confection and I’m nearly giving up. My eyelids are sagging so much that I get my mascara and eyeliner transferred onto my lower lash line . Have you tried “Lids by design “ eyelid tape ? I purchased a set and it makes a huge difference on the appearance but still, eyeshadow application is tricky. Recently, I have ordered City beauty’s eyelid treatment/ primer, will update you after I try it. Thankfully, besides my eyes I don’t have major skin issues. And have been for years counting on my favorite IT cosmetics CC cream and recently switched to Giorgio Armani luminous silk foundation with its companion “power fabric” concealer . The foundation is on the pricey side but a little goes a long way as it provides good coverage.
    I feel like most brands ignore the mature age group and the fact that we have bigger buying power than the youngsters. As for tutorials, have you watched “painted by Spencer “ ? Y. He has a couple of good videos done on mature women.You may find me at his chair one of these days, he is local and I’m dying to get a makeover by him.

    • Cindy Hattersley says

      Hi Liana

      Oh boy the eyes!! I always look like I have my eyes closed in photos! I wondered about those strips. I am going to check them out. I think brands are getting better about including our group but they have a long way to go!! I am going to check out pained by Spencer. You always have such good suggestions!!

  6. kim says

    Cindy I love this post ! You rock those boots with the cool striped skirt and when I saw the pic of you in Carmel the other day with the jeans and the big sweater with the boots, I really thought I need them! They make your outfit look chic. Now I’m in Utah for the weekend and everyone has them here- and looks very cute. I love all the choices you posted too and I think the Vince ones are what I will order! Always you have looked cool and were on what’s chic before everyone else- inspiring me.
    Kim

  7. SUzanne says

    OMG!!! The tulle skirt outfit–LOVE it! I need it…and a place to wear it. I have always loved chunky boots. Can’t think of any shoe worse than ballet flats and kitten heels.

  8. Sheila-Merle Johnson says

    I’m 76 and I got a pair 2 years ago- at Macy’s or Kohl’s. I have narrow feet and it took a while to find a pair that had the combat boot look but weren’t too heavy or wide. I’ve only worn them with cuffed jeans and leggings, so far, but I just bought your gray flouncy skirt and I look forward to that. They do have to be balanced with something feminine for my style. Wearing them with jeans or leggings and not wanting to look too young means wearing something not only feminine but a little sophisticated on top. The thin turtlenecks you featured are just what I’ve been looking for. Plus I loved the striped skirt in the last couple of photos. Is that available? I haven’t worn a skirt in years. You’ll get me into one yet!

  9. sharon says

    This reminds me of the trend of wearing cowboy boots with mini dresses….so adorable on young gals. I bought a pair and still wear them with leggings or skinny jeans as the mini look passed me by many years ago! You look adorable in your boots bc you keep the scale in line. Love the skirt with them too!

  10. Pam says

    I have a pair in my closet. I was going to wear them today. But changed my mind. I should have worn them, my trusty pair of brown booties, I wore today are shot. They are heading for the trash. So I guess I’ll be wearing my combat boots more often. They have a better sole too. And I need that where I live.

  11. Nancy says

    Love the skirt and love this post. I’m 64 and have been debating “shouldI?” You just pushed me over the top. I’ll be looking for a pair to go with my sweater dresses! At the Bank! 😉

  12. Sally says

    Congrats to all of you that want to wear combat boots as a fashion statement, but after spending 26 years wearing them as part of my military uniform (USAF NC), I’ll pass…☺️

  13. holly says

    If I wore combat boots: 1. my dog, Boop, would give me side-eye; 2. my husband would check my temperature; 3. my 65+ neighborhood would call my husband to see if he checked my temperature! I would just feel silly. They sure are cute on you though!

  14. Nancy Brantley says

    I’m yay…I say wear what looks and feels good on you! Age has nothing to do with anything u less that’s how you feel about yourself. Like commenter said these type boots use to be only wealthy could afford to look stylish.

  15. Lauren says

    I don’t see these as combat boots….work boots and combat boots have a big “ball” of toe box designed to protect the foot from all kinds harm and a tall lace-up shaft. The boots that I see for women hark back to an earlier time when all women of a certain class wore boots….practical solid boots and they probably only had one pair. Only wealthy women had the luxury of wearing shoes. If you find a pair that fits (and you don’t overdo the heel height) the boots can be VERY comfortable and practical. I have an insulated version from Pajar a couple of years old now that are Winter boots because unlike you and your friends there in California I live in Canada where we have Winter. They keep me safe as I slog into the grocery store and they look good enough to get compliments. 🙂

    • Cindy Hattersley says

      Hi Lauren

      Great points. I grew up in the Midwest and slipping and sliding on ice was a problem as a child, I can only imagine the challenges now. Thanks for putting things in perspective. You guys are the best!

  16. Annie Diamond says

    Cindy! Not only am I now obsessed with combat boots but every one of your looks! With jeans and a sweater or one of your amazing statement skirts or the sleek head-to-toe black leather look, the combat boots just put an exclamation mark at the end of each outfit! You are a rock star!

    • Cindy Hattersley says

      Annie you could totally pull them off! They have Annie Diamond written all over them! So fun having you! Sure wish you would move back to California!

  17. Laura says

    Right on sister girl! Wear what makes you happy. I have the tulle skirt in my basket right now. Hope it will be long enough for my 5’10” body…..

  18. Marcia Rayne says

    I was shopping in TJMaxx , just window shopping, and my eye caught a pair of tan suede lug sole combat boot. No laces, just pull on.. They were light, not heavy. And the color was great. I did not want to invest a lot. After all,Christmas is coming up. But a snagged them anyway. I am going to wear them with boyfriend jeans and sweaters. Maybe a blazer. ( I have always loved sweaters.). I plan on wearing the boots on Election Day as I am an election judge. Thanks for the post! Your house is looking spiffy! Where is that cute Beau?

    • Cindy Hattersley says

      Hi Marcia

      We have to have some fun with fashion don’t we? I LOVE sweaters too and of course boyfriend jeans. Comfort is big as well. Thanks for always weighing in. I always enjoy your comments so much!

  19. Terry says

    I would wear combat boots if I were going into combat, but otherwise? Not even in my coffin. I like pretty, delicate shoes – ballet flats, embellished thong sandals, kitten heels, embroidered booties with stacked heels – maybe even a sleek riding boot, but that’s as far as I go. As for the look on others, I wouldn’t call it appealing but I am a fervid proponent of personal style so you do you.

    • Cindy Hattersley says

      Hi Terry

      I heard from a few other women from the military on Instagram and they resoundingly agree with you. I think they all got a big chuckle out of this. That’s what makes the conversation fun.

  20. Margarita W. says

    I am 68 and petite still wear my combat boots love them but I have small feet size 5 1/2 . So as long as they aren’t too chunky it’s a go for me.

    • Cindy Hattersley says

      Hi Margarita

      I agree with the not too clunky at least for me personally. I have seen others pull it off and look fabulous. We just need to have fun at our age!

  21. Karen says

    Omg, Yessss and want the ones ya have, why is it Size 10 med width hard to find at times? Poor John l, Size 16 Shoe size( 6’8”

    Love every kind of Boot, Tho like ones that I can easily slip on too Waterproof, Key,Ice, Snow, Rain grrrrr

    My opinion to me has nothing to do with this Age/ Number thing., I want to stay current
    in attire…….

    Now it has come down to
    Rags( Never Ending Projects, Oils, Pants, Stains etc), Casual attire, Lot of Winter Garb😩❤️

    Ohhhhhh mannnn miss Big D days dressed to the max..

    Cindy:
    I would soooo Shop ya closet, Love Love ya wardrobe.
    Thank you

    • Cindy Hattersley says

      Hi Karen

      We have to keep things fun, don’t we? Especially after the year we all had. Sometimes it is fun to think outside the lines and enjoy it!

  22. Nancy says

    When you wear a size 10 shoe….
    No white shoes, no combat boots, no Ugg’s, they all look like I’m wearing water skis😂

    Combat boots look good on you!

    • Cindy Hattersley says

      Hi Nancy

      I hear you!! My feet are not small, and tend toward wide. I have to be careful too!!

  23. NATALIE K says

    Love this post!! I have wanted a pair of combat boots but I mentioned it my mother she said I had no business wearing them a 55!! So I bought a pair of black suede lace up boots but without the junky sole!! Love them but not the same tough feeling.!! I love them with your tulle skirt!! Blue isn’t my color though!! So, now you have me thinking!! Should I get a pair of combat boots??!! I do love my Doc Martins with the ribbon laces!! I think I’ll pull those out!!

    • Cindy Hattersley says

      Hi Natalie

      That skirt is so reasonable and comes in a ton of colors. I had planned to order the black and thought the blue would be more gray (like my hair) but ordered it for fun anyway. At $29 you can afford to take a chance.

  24. Kathryn says

    Love this post……I’m going to incorporate my 20 year old Harley boots with some of my non Harley apparel.

  25. Vicki says

    I love wearing booties and some are substantial enough to be considered an combat boot. I don’t think there should be any age restriction. I’m 66 and wear what I like. I wear a lot of sneakers too. My other love is brogues. Love this post and seeing how everyone made the look their own. 🤍💗

    • Cindy Hattersley says

      Hi Vicki

      I agree we need to just wear what we love at our age. Linda made a point that we don’t want to look clown-like. It is a fine line. Lucky for me you readers always keep me in line!!

  26. Liana says

    I love the look of combat boots and how you styled them . I’d love to dip my toes on this trend but I carry my weight on the legs, so
    chunky shoes make me look even chunkier. I’ve just ordered a pair of high top black platform vans that somehow gives a similar grunge vibe to combat boots and will see how that goes. Your Florida’s maxi skirt is to die for…

    • Cindy Hattersley says

      Hi Liana

      I love vans but just find them uncomfortable. Mary Ann loves them and can wear them because she doesn’t have bunions! Isn’t that skirt clever. I bet you could make one of those.

  27. Candy says

    I am all for comfort because I too have a bunion issue.. Cindy, I think you can pull them off. However, at 73 it would be a no for me unless there is an affordable, subtle, super comfy pair out there that does not make me look like am trying too hard to appear hip/cool/younger. Your fashion posts are the best and have proven over and over again to inspire and take me out of my comfort zone.

    • Cindy Hattersley says

      Hi Candy

      Darn the bunions!! I am sure you find it hard to find stylish, comfortable shoes that aren’t a fortune too! So glad you always enjoy the posts. You ladies constantly inspire me to think outside the box. I try to find something for everyone.

  28. Mary from Life at Bella Terra says

    Cindy, no combat boots for me….when I think of combat boots I think of the huge, military style boot, not the scaled down version. I think it clearly depends on the shape and length of your leg. Some of the pictures above are nice ankle boots but not what I would consider combat ones. However, it is certainly a personal choice and you can apparently pull it off. Good for you! When someone wears them, I tend to focus on the large boot vs. the person overall. I also think if you are in cold weather, they make more sense. Not such a common fashion practice in warm Phoenix. Fun post!

    • Cindy Hattersley says

      Hi Mary

      I am glad you enjoyed the post. I knew it would be great fodder for conversation. I have to say I am loving my boots but couldn’t pull off the clunkier version for the reasons you have pointed out.

    • kim says

      I disagree. She looks chic and current and perfect for her age. Wear what feels good and looks good and Cindy looks great.

    • Cindy Hattersley says

      Hi Linda

      Ha! I knew the skirt would spark strong opinions as well as the boots. That’s what is great about our group, we aren’t afraid to share our opnions! That’s why I enjoy you all so much. P.S I think Summer would like that skirt.

      • Judi says

        My daughter said that Dr. martens are the iron skillet of boots! I agree. I am 64 and love the comfort and style. I do mix with feminine elements.

  29. Joanna says

    I like the more refined combat boot as you’ve shown but not the lug sole boots. They look too heavy fir my aesthetic. But if your personality is one that likes the edginess of the look, go for it! I don’t like to put an age on fashion. It should be fun, right ladies?

    Cindy, you look so cute in skirts. I find they make me look bigger so I avoid them. That flared skirt with the wrap waist is fun!

    • Cindy Hattersley says

      Hi Joanna

      Isn’t that skirt from Nicole Paloma fun? Such a clever design. I struggle with dresses because I am long-waisted. I have always loved skirts (as long as they aren’t short). I agree about the combat boot look at least for me. The sole has to be just right, not too clunky, as well as the body of the shoe. The Stuart Weitzmen McKenzie is perfect, try to find on Ebay as I did. I certainly wouldn’t pay $500 for combat boots. I will say I cannot buy cheap shoes anymore due to my foot issues however!

  30. Char says

    Another post I love!!!!!! I love all those looks and I love my combat boots!! I bought a pair of Sam Edelmans with a lug sole and they are comfortable and not too heavy and they have a Prada look to them. I love a little edgy look. There are so many choices to choose from and many that are a little more streamlined if Doc Martens are too clunky ( I still love them!)
    You look so cool!!😜This post will be kept for inspiration now that it is cooling down.

    • Cindy Hattersley says

      Hi Char

      I am so glad you love them. I do too. I do agree with some of the other readers that one has to tailor them to their own taste. I could not wear the Doc Martins (though I love them on others) because my feet are too clunky! We gotta keep it fun at our age!!

  31. Alexis says

    I sent this to all my retired combat nurse friends we all agreed it was a hard no TeeHee.
    Maybe if your slightly over 50 but not over 65 , we can’t believe combat boots became a
    fashion statement. We do think your adorable Cindy and love the skirt I plan to order one .
    I noticed the ads that are popping up with this post are for beautiful heels to funny , I plan
    On ordering those too !

  32. Karen B. says

    I’ve been looking for a pair. I want a pair that is fairly subdued but clearly combat boots. Yours look great and I love them with leggings and jeans.
    xo,
    Karen

    • Cindy Hattersley says

      Hi Karen

      It took me awhile to find the right ones. I agree I did not personally want a real chunky pair. I hope you find some you like, they sure are comfy!!

  33. CHristine says

    After wearing so many shoes and boots that weren’t comfortable or easy to walk in for long distances, combat boots are wonderful! I love the look and if you’re hesitant about wearing them, try them under long pants—they don’t look much different then oxfords or booties.

    • Cindy Hattersley says

      Hi Christine

      I totally agree. I was so glad they have become fashionable. Comfort is key at my age!

  34. GayleMiller says

    Cindy, I don’t own a pair, because I wear sandals most of the time, but I’m not opposed to them. I can’t wear heels anymore because of my knee problems, so sturdy boots might be on the horizon. Not every piece of clothing suits everybody, but these surely suit you! And that skirt….

    • Cindy Hattersley says

      Hi Gayle

      I go from sandals to boots in our climate with time for some slides in between! We have to do what we love, right?

  35. dianne says

    oh yes!!!! I have 2 pairs of Dr Martins and wear them all the time! I love an edginess to my style – always!
    Really, Docs are very cute with skirts/ jumpsuits, jeans and legging.
    Glad you posted this to inspire …

    • RobBie B. says

      Absolutely! I wore doc sandals this past summer and got tons of compliments. My feet are 7 1/2 so I think it’s easier for me to pull them off. I have boots for fall and winter. Very comfortable.

  36. Gray says

    That’s a hard no for me. They seem contrived when anyone wears them, unless they’re in the service. IMHO. 🤷🏼‍♀️ That’s just not my look. But it’s still a free country – go for it!

  37. 1010ParkPlace says

    I think the boots look wonderful on you! Like leather, I don’t think we’re too old for them. A mini skirt, yes, but combat boots, no. Loved doing this blog with you Cindy! xoxox, Brenda

  38. Merilynn says

    They look real cute on others but after having to wear them for 20 years in the Air Force it’s a definite NO for me. I always couldn’t wait to get those heavy things off my fee. Too clunky, and heavy. I cannot believe the fashion industry is trying for these to be mainstream, just looking for a way to change things up I guess.

  39. jill Valeri says

    I love my combat boots! I actually have two pairs. One is black patent leather with a lug sole and the other is more refined with a higher heel and croc embossed. I find that they are a stylish way to wear a supportive shoe.

  40. Janelle says

    You asked for our opinion so here goes..they are not for me. I just can’t. You totally rocked the look though. I guess I’m not as fashion forward as you girls are. I don’t mind seeing them on younger gals in their 20s and 30s, but for me at my age it’s a no.

  41. AJ says

    Love this post! I just bought my second pair of combat boots and love them (I am 72 yo). That blue ruffle skirt is a show stopper; you look fabulous in it. I don’t think I could pull it off, but I will be checking out the Nicole Paloma website.

    • Peg says

      I’ve been wearing black lug sole boots from timberland for 15 years!!! Same pair!! And a couple of other pairs too
      I’m 64
      That Blue skirt!!! First dibs when you’re done with it…

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