Would You Wear It – Combat Boots and Skirt

Happy Saturday, ladies. If you’re new here, welcome! Grab another cup of coffee or tea and let’s have some fun with fashion.

On Saturday, my friend Pam and I share a mannequin we’ve come across and ask if you would wear what it’s modeling. I love us to also swap styling ideas in the comment section so we can inspire each other. It’s easy to get into a styling rut, and the other gals here have fabulous ideas, so please share yours.

I spotted this mannequin at a store in Vancouver, BC last month so I have no links for you.

What do you think? These lace-up ‘combat’ boots are very popular this winter, as is the chunky knit of the sweater.

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What are your thoughts? Could you wear this look? What would you change or how would you style it to work for your shape and lifestyle.

In my cart this week-

You may remember that I wash my cashmere on the gentle cycle in cold and hang it to dry. Last week, a helpful soul put them all into a hot dryer so they’re now all felted sweaters that would fit a cat. Most were quite old, so rather than make myself crazy trying to rewet and possibly stretch them, I hunted down some sales-

I bought this cashmere turtleneck in Blue Azurine in medium to add some slouchiness. They’re marked way down and winter is just beginning. The blue has a brightness that appeals to me and will look great with denim.

I also ordered this cashmere v-neck in this Blue Resort Heather, also in a medium. This cheery blue will perk up anything I wear it with and as the days get grayer, the more I will crave color.

This compassion fund scarf caught my eye when I was in J. Jill this week and came home with me. I love the embroidery and that 100% of the net proceeds from this exclusive style will support and empower women in your local communities through the J.Jill Compassion Fund.

Weekend Sale Updates


NORDSTROM – Black Friday Deals up to 40% off plus earn 3X the points

ANN TAYLOR –  4 days of deals. 50% off dresses and shoes, 75% off outerwear, 40% off sweaters, and 30% off pants and denim.

J. CREW FACTORY – up to 60% off the entire site

ATHLETA – 20% off Black Friday access through 11/14

J. JILL – 25% off full-priced sweaters

LOFT – 50% off 3 styles, 40% off 2 styles, and 30% off 1 style

MACY’S –  Black Friday Early Access with specials throughout the store

Now let’s go see what Pam’s mannequin is wearing at Over 50 Feeling 40

Thanks for reading ladies and remember to wear what makes you feel confident.





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  1. I would love to try on the sweater, I really like it. Although, I would not wear it with the skirt. The whole outfit is too voluminous for my body shape. I would wear the sweater with skinny jeans.

  2. Carol Blum says:

    No combat boots! Iffy on the skirt…yes to the sweater….

  3. No, I would not wear the combat boots as shown. Just not my style. I do like the sweater and also the skirt. Not sure together ? I had to laugh about your sweater experience. That has happened in our home several years ago !
    I luv the cashmere sweaters you ordered. Did you order your normal size ? The colors are so pretty to wear this time of year. Have a great weekend.

  4. GriselleCC says:

    Not really, not even if I was younger. Boots are not my style and the sweater and the skirt are too bulky. Too much fabric and overall not flattering.

  5. My heart dropped into my stomach when I read what happened to your sweaters. I would have sat down and cried ( or screamed). I guess I am “lucky” that no one helps with the laundry here.
    As for the WYWI today, The colours are off, but I got a great idea for one of my lighter weight micro pleated skirts and a bulky cowl neck. I would not wear the boots, but instead wear a pair of tall, grey, flat boots that the skirt flows around. I am in love with the scarf also, and alas not shipped to Canada, but a great idea to keep a look out for something similar. This is why WYWI is helpful even if the items are not in my colours or exact style.

  6. I’ve worn skirts w/ sweaters & any boots all my life. Some outfits are (far) better than others, but it is my “uniform.”
    One thing I won’t wear are the shoes with large soles that are wider than the upper. Not only would I trip clumsily along, but they would make my feet look huge. I do love lace-up boots of all kinds, but the trend of a larger-than-upper sole is one I’ll pass.

  7. Vicky Butera says:

    Love the skirt and sweater, but not the combat boots for me. They just don’t look comfortable. At my age feminine and comfortable, the latter being most important, is what I am all about. ❤️
    BTW love the blue v-neck sweater.

  8. I love the skirt….can you share which store in Vancouver BC you saw it? Have been searching for a skirt like this to wear with my slouchy cotton sweaters. The combat boots are a little too much for me but a pair of more refined lace up boots would be great.

    1. This outfit is from Massimo Dutti. I love that store:)

  9. I would wear the sweater and skirt, but not the combat boots. I think wearing some low heeled booties or riding boots would be my preference. Add a scarf and jewelry and you have a stunning outfit! Love the cashmere sweaters! They are definitely a plus in my wardrobe..

  10. I’m going way out of my box with both my first response here (long time follower though) and by saying that it appeals to me. I would absolutely try it on. I’d have to be sure I could wear the outfit and not, the outfit “wear” me. I envision it on a tall slender body but even at 5’4″ and 115 lbs, I’d give it a try. I find myself liking some combat boots and yes, they are everywhere. So sorry to hear of your cashmere sweater mishap. Can anyone tell me if someone allergic to wool, can wear cashmere? I’d love to own one but have always been afraid to invest in one only to find myself itchy and scratching while wearing it.

    1. I struggle with wool but can wear most cashmere. I find it trial and error because some cashmere is scratchy so you almost have to try them on.

  11. I can really see someone young in this outfit. As for me it would never work. These types of skirts are just to much for my small frame. I like the sweater and I think combat boots are great but again for the younger set. Really love the blue sweaters. Would wear those with jeans.

  12. He-who-shall-not-be-named in my household also did the hot dryer/cashmere catastrophe! My sweaters actually fit my dog; best dressed dog in town, ha! Thank you for the info on the scarf. I just ordered it using my Jill birthday coupon. The cashmere sweaters also come in crew neck style which I find easier to wear. Regarding the mannequin, no to combat boots. I do like the skirt, but would prefer one of your cashmere sweaters with it. I would wear tights and Tieks with the outfit.

    1. LOL!! So happy to here I am not alone with the laundry “help”:)

  13. The sweater, skirt, and sweater have too much material for my petite figure. I would wear the sweater if it was not over sized, and a “no” for the skirt. No for boots, I would wear black pants and black ankle boots.

    I my opinion, if you look good in it wear it.

  14. I had a similar skirt in high school (40 plus years ago) that I adored. No, to the combat boots, I wore them way too much while I was in the Air Force. After a 12 hour day I couldn’t wait to take them off!

  15. That is possibly the ugliest skirt, but I really love the sweater and I would for sure wear combat boots with a long casual skirt and sweater or shirt and blue jean jacket or down vest situation. Some of these mannequins are just so bad. Stores should try a little harder.

  16. I really like the look…I think the proportions work well together. I like combat boots, especially slightly sleeker ones like these. I wear them with jeans. I don’t wear skirts, especially long ones just because…well, they just don’t feel comfortable on me. But I think this is a great look on somebody else. And the blue sweaters are gorgeous!

    1. I’m hunting for a sleeker version myself. For comfort, and for style.

  17. I will be 61 & love the combat boots! Finally found a pair to fit my large narrow feet(10) ! Outfit, concept yes, I like. Color, fabric & style not as much. Sweater would be too hot, I’m not a fan of high necks. Don’t care for gray with muslin colors. Excited to start wearing my boots with everything!

    1. Christine says:

      I agree! Combat boots are heavenly for those of us with narrow feet, and so comfortable. Love the look.

      1. I did not know they were good for narrow feet! Thank you for sharing

  18. Aargh……”these things do happen”…. I would wear the mannequin look, but different color combo or add a scarf since the gray just doesn’t work for me. I have these boots with brass studs and blinking lights in the soles🤣🤣🤣

  19. Ugh. No way. Not a fan of combat boots. Reminds me of the “goth” look of what, about 20 years ago? Not really for my age category I’m afraid. The sweater is the only part of this outfit I may consider. I do love the look of the J. Jill scarf! Happy Saturday!

  20. Although in my 70’s, I’m not opposed to an edgy look. At my 5’ 4” height, the skirt would be a maxi on me. The sweater is way too oversized. I have been thinking about how comfortable and practical combat boots would be? If you could show us, more ways to wear them, in a more fitted look? The blue sweaters are nice.

  21. “Helpfull soul” oh NO!
    Today’s outfit is not for me. The sweater is too slouchy, the skirt too full and I just don’t like the combat boot look. The boots look so heavy and clunky.
    I like the cashmere v-neck. Great color!! Happy Saturday!

    1. When I read “helpful soul”, I immediately thought, did her hubby try to help with laundry?!? 😆 Mine knows better after a similar situation years ago!
      I’m not a fan of combat boots, or the entire outfit in general. I’m late 50s and only 5’1”, so it just wouldn’t look great on my hip-heavy frame.

  22. the combat boots are kinda cute on much younger women. but as a much older woman, plus wearing a size 9…..I would turn heads in the wrong way if I tried these….

  23. Love it but would change the skirt color to black, making my legs appear longer.

  24. I’d wear the boots and sweater and swap the skirt for any width jeans. In fact, I wear that type of outfit to my job these days – high school teacher in Vermont. I don’t know why, but when cold weather hits, I bypass all of my dresses and skirts in the closet.

    1. I’ll modify my response by saying my combat boots aren’t quite as chunky as what my students wear (massive Doc Martens). Mine are sleeker – one is the Frye Sabrina and the other is a Vince slip-on. My students like them, I like them, and they’re not too young-trendy.

    2. I’m guessing they just feeling warmer, I know they would for me

  25. I like the look of the sweater but the skirt is not a good style on me. I would pair the sweater with a pencil skirt or straight leg slacks. I don’t plan to even try on combat boots, just not attractive to me. I am looking to replace boots for winter. Not looking forward to Michigan snow and ice. The cashmere sweaters are a staple for my closet, really like the turtleneck. Love the 50’s on Instagram. Susan’s packing tips, your try on diary and would you wear it are great for new ideas.

  26. I like all three pieces, just not together. With the skirt I would wear a leaner top, with the sweater, a leaner bottom. I like clothes that at least suggest a body underneath, even if it’s just a fitted sleeve. My feeling is that if the mannequin looks heavy, I will look heavier!
    Also, I like neutrals, but there is something about the cool sweater color and the warm skirt color together that I wouldn’t wear.
    I’m not sure where I would wear the boots, but I do like them.

    1. Great observation about the cool sweater and warm skirt

    2. Hi there! I am new to the blog. Been following on Facebook for quite some time. I just turned 60 and need new oomph in my style which is classic but colourful. No to combat boots. Love the sweater and the skirt, but not together

  27. What a fun look for someone young! While I like both the sweater and skirt, worn together, it’s too much volume for my 64 year old body. Combat boots don’t match my classic style. I would feel as if I was in costume. I don’t respond often, but I do enjoy your informative posts!

    1. Thanks for being here with us, Deborah

  28. SuzanneGabrielle says:

    I was recently in the North Carolina mountains for a wedding weekend. I wore a chunky sweater and midi skirt to brunch, but with my regular high boots. I don’t own or plan to own combat boots.

    1. So was I! Wouldn’t it be coincidental if we were at the same one.

  29. I’m inspired by this look. Chunky sweater and skirt – yes. Combat boots – no. (Even though they are so on trend, I haven’t found a look that wouldn’t be too heavy and masculine on me). Other favourite boot styles – yes – chocolate flat, tan suede, chocolate suede ankle, etc. If possible, I’d go for a slouchy sweater in a plain colour as close as possible to the skirt colour. I’d add robust gold earrings. And then have the dilemma of which coat to wear (although it would be in warm tones – whether brown, tan, rust, etc)

    1. Maribeth Conklin says:

      Great look for high school or college girls. Together not my style at all. Might wear the sweater or skirt seperately.

      1. Jennifer, the two blue sweaters you show are beautiful! I would wear them with ivory cords and booties. The outfit on the mannequin, however, doesn’t appeal to me: the sweater is too bulky and so is the skirt, and combat boots are best left to combatants.

    2. Brown would be gorgeous

  30. Paulette Levy says:

    Love the blue cashmere sweaters! They will perk up any rainy or grey day! Gorgeous!
    Onto the mannequin. I see combat boots everywhere! But this long skirt and sweater won’t be in my closet. Other than liking the neutral tones, I don’t see myself wearing this, and if I were to wear it, I might pair with taller leather more traditional riding boot. I’m just not a fan of combat boots for me.

    1. This would look more elegant with the tall boots:)

    2. Lorrie Orr says:

      No to the combat boots with the long skirt. Tall boots would be more elegant, in my opinion. I do love the fullness of the skirt.
      Your cashmere sweater story had me smiling!