Fashion Friday: Boots and Skirts

When I asked for Fashion Friday post ideas a few weeks back, DeAnn had a lengthy comment that included at least a month’s worth of Fashion Friday topics!  This is an excerpt:

What do you think about the lace-up boot trend? I’m trying to be open-minded but I keep thinking about Laura Ingalls Wilder. Hmm…what else? I usually work the long skirt and boots look throughout the Fall and Winter. I’m getting a little tired of my frumpy long skirts. But…I also don’t want to go too short because I have lots of little kids and kneeling at church so modesty is important. So, how does one rock the skirt/boots look when you’re over 35?

Ah yes, the lace-up boots.

Photos compliments of Nordstrom.

I’m not a fan, really.  It doesn’t mean that they won’t look good on YOU!   But I’M not running out to buy a pair.  That doesn’t mean that they couldn’t be smashing on the right person in the right city with the right lifestyle.

I’m actually KIND OF liking the pair on the left up there.  The more I look at them, the more I can imagine them trotting around town under a knee-length pencil skirt, going to a sophisticated office job where there is no drool or sticky jelly fingers or needy preschoolers . . .

But for me?  And my everyday life?  I’d feel kind of silly.  BUT.  Ask me next year.  I used to think I wouldn’t tuck my jeans into my boots and now I don’t wear them any other way!  Styles have a way of growing on me.

As far as your next question:

how does one rock the skirt/boots look when you’re over 35?

I used to wear knee-high boots with knee-length skirts to church all the time when I had young kids.  (I realize I still have young kids, but I mean when they were REALLY little, as in, I was in the nursery, on the floor with them.  Of course, I was also barely 30 years old.)  But, I think as long as the skirt comes to the knee, you can be modest in it.  You just have to be aware of how you sit and bend, and do so in a way that doesn’t provide a show that you weren’t expecting to offer.

It’s really these mini-skirts that are coming back into vogue that are causing all the problems.

Like this? No no no no NO.

Remember Stacey and Clinton?  NO MINISKIRTS AFTER 35!

But these?  CUTE!  Stylish.  Sophisticated.  Age appropriate!  Just envision them with boots.

Skirt photos compliments of Nordstrom and Ann Taylor.

I particularly like the length of the one on the far right, I think it can be very flattering IF the proportions work.  By that, I mean, that almost no one can get away with a skirt that falls just below the knee and flat shoes.  You must wear heels to give enough distance between the bottom of the skirt and the ground to even out the proportion created by a longer skirt.

In the same way, sometimes flats look better with a skirt that hits above the knee.  I like my flat boots with shorter skirts.  I feel gangly in heels if my skirt is short.  It really depends on your body type, though.  If you’re under 5’2″, then you can wear heels with just about anything and pull it off.  Whereas heels often make me feel overdressed.

Boden has a TON of great skirts for the mom over 35.  And they actually help us out by picturing them with boots.  Like, take a look at these:

And remember.  Models are often taller than us average Joes, or should that be average Josephines?  Anyway . . . usually they will appear longer on YOU.

Boden also tends to carry a lot of A-line styles, for those of you who prefer that cut of skirt.  I’m a huge pencil skirt fan, myself, but I realize that an A-line cut is easier to move around in and probably provides more modesty.

Anthropologie also offers a lot of mom-friendly skirt options, if you like their styling.  They are showing a lot of these fuller knee-length skirts, which, again, should provide a mom with enough modesty to feel comfortable bending down with young kids without compromising style.

Yes, Boden and Anthropologie prices are sometimes staggering, but you can use these ideas anywhere you like to shop.

What about you? Do you wear skirts with boots?  How do you rock the skirt/boots look when you’re over 35?

For more Fashion Friday posts, check these out! (Or add your own.)

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21 Responses

  1. I don’t get the look where you can see the knee high socks just peeking out of the boots… (like your photo of the mini-skirt look).

    How is that a “look?”

  2. This was just the dilemma I was discussing with a friend this week- perfecttiming! I have 3 friends (all over 40) who rock the skirt/boots look- they all wear A-line skirts. Couldn’t find a single one at Kohl’s, thanks for these pics for more ideas!

  3. Great tips! Makes me kind of sad that I’m in the over 35 no miniskirt phase but I do know I’d look ridiculous if I wore one.

    LOVE those skirts from Boden. Just love. And I need some new good boots. I have a Fashion Friday post scheduled in another hour with some boots I’m thinking about. I’m def going to order a pair from somewhere soon.

  4. ok I am definitely over 35 – but I love a skirt and boot – for work/dressy, I pair opaque stockings with heeled boots and work skirts. For casual, I like a lower-heeled boot with tights. I own 2 pairs of black knee-high boots and 2 pairs of brown knee-high boots – a high heel and low heel option in each color – then of course a low heeled, ankle boot for pants and jeans =)

    ahhhh boots. . .btw LOVE those Boden looks – my catalog is worn out from paging through for outfit ideas.


  5. I LOVE skirts with tall boots. I’m not a lace-up girl either but that’s just me. I think if you can rock it, do it. But I love the kind that aren’t as fitted and are tall. So fun. I still rock out my cardy uggs with dresses and leggings. They are fun!


  6. I just wore a skirt and boots this past weekend. But I’m not 35. 😉 I will probably be wearing the look more often this winter, at least until I lose enough weight to get back into my winter dress pants. I want some flat boots, but alas, no cash for that when I have a pair of brown boots and a pair of black boots still in great condition, with heels. At least I’m short. 😉

  7. Thanks so much for answering that question. In my dream world, in which I am an amazing seamstress instead of just being able to thread the machine and sew straight lines, I really want to make my own skirts…or at least be able to hem them myself. They seem so easy to make. Ahh…someday…

    Love Boden and I always think I love Anthrpologie, but after much ordering and returning, I think I need to give up. I always try and always look ridiculous. Not for short folks with a few extra lbs. to lose. Oh well. Lesson learned…stick with the classics.

    After 3 years of looking for black boots and just putting it off ’til “next year” I finally ordered these (With a 30% off coupon ) …https://www.garnethill.com/b-26-23248-3brn-heeled-boot/womens-fashion/footwear/boots/12238

    Now I’m going to check out some of those skirts!!

    Thanks again!

    P.S. Boden has a sale going on right now–if you buy two items, you get the third (of = or lesser value) for $1

    1. I love how you correct your typos. I think we’re twins separated at birth. 😉

      I am the same with Anthropologie. I can’t wear their stuff. But it’s adorable. I have a love/hate relationship with Boden. I haven’t always been pleased with the stuff I’ve ordered. I love LOVE the styles but they don’t always work on me. I do better at Banana Republic.

        1. I’m shopping with you for the boden sale. I’ve always been afraid to order because I didn’t know if they would fit.

  8. What a great topic – I’m actually wearing a skirt with boots today! And I’m just under 2 months from being 36. I don’t have lace-up boots, except for my winter snow boots, that is! I love wearing knee-high boots with a knee-length skirt, or one just a bit longer. I think it’s a great look. I’m more of a pencil skirt girl than an A-line skirt girl, because the former is more flattering to my figure.

    Right now I’m wearing a long Cabi suede skirt that’s mid-calf length in the front and ankle-length in the back, with knee-high black heeled kenneth cole boots. I love the look and wear it often.

  9. Love the look of boots and a skirt. But I agree at 35 I need to wear knee length skirts. The minis are really short this year…I ordered some from Old Navy, figuring because I’m short they’d at least come to the top of my knee, but nope barely covered the goods…crazy. Anyhow the only look I’ve got right now is a denim skirt that is a bit more ample than a pencil and less than an A with casual worn in brown boots I got at target. I do brown tights for a one color look. I try the bots on with lots of stuff but haven’t found another dress, skirt that works yet. Thanks for this post.

  10. Tights tights tights! I like to wear tights under skirts when I wear boots with them. I either match the skirt or the boots…depending. Helps to keep me modest, “together” and slimmer.

  11. Ooooh you showed the Boden skirt I’ve been drooling over ever since the catalog arrived at my HOUSE!. I gotta break down and just buy it already.

  12. So happy to be here! I say you can totally rock a mini skirt with boots after 35 and yes even those of us over 40. You have to be confident in it, and wearing the right shirt and accessories will compliment you. I’m looking for a pair of thigh high boots this season and I will be rockin them with a mini. Of course I’ll be careful with sitting and bending- you don’t want to be a hoochie!

  13. I passed 35 a while ago. I love my boots, and have several pairs. Plain black, nothing fancy, roper cowboy boots, blue cowboy boots with white stiching, caramel (love these best) cowboy boots, black equestrian boots, and brown, low heel, lace-up, with a zipper & some buckles boots (may sound like biker boots, but not). I wear my boots a lot of different ways. I do not wear minis, but do pair my boots with tights (or leggings) and knee length dresses, calf-length skirts. I have even paired my blue cowboy boots with my long, sleeveless, black velvet dress.

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