Keep or Delete: A 16 Year-Old Houndstooth Skirt

Happy New Year!

A new year has arrived. It’s a perfect time to take stock of the past and put together a plan for the future. Since this is a fashion blog, I’m using this occasion to take stock of my closet. I got the idea from a fellow over-40 blogger, Julia from When the Girls Rule. She asked readers to help her decide if she should “keep or ditch” a holiday top she had never worn. My thanks go to Julia for the inspiration!

My “keep or delete” item is a houndstooth skirt I’ve had for 16 years. If it was a person, it would be getting its drivers license this year. In all that time, I can count on one hand the number of times I’ve worn it.

Why keep it?

This skirt was part of a group of things I bought from the now defunct Zenobia of Canada. (I still mourn the loss.) The materials and the craftsmanship are the highest quality of any clothing I’ve owned before or since. Other items from this collection that I wear regularly still have the look and feel of something almost brand new. In addition, the colors, patterns, and cuts are timeless. They never go out of style.

This skirt is no exception. It’s hard to know whether it was created 16 years ago or just this past year.

It simply feels irreplaceable. I am no longer willing to pay the money I spent 16 years ago and I’m afraid I would regret giving it up.

Why don’t you wear it, then?

You would think I would wear it all the time. You already know I love plaid. Over the last several months, I’ve written about little else.

1. Plaid orange skirt | 2. Houndstooth plaid pants | 3. Grunge plaid | 4. Christmas plaid

In addition, you’d think I’d be able to pair it up with almost anything in my closet. It’s essentially a neutral. And, as I mentioned above, houndstooth is timeless. It never completely goes out of style. It’s been around since at least the early 1800s.

When I said houndstooth was timeless, I wasn’t thinking about the suit pictured above worn by this Civil War-era gentleman. All I can say is, WOW!

My skirt has all these great things going for it, but I rarely think about it. For so many years my wardrobe skewed black and denim. As a result, most of my accessories and coordinating items go with black and denim–not brown. In addition, at some point soon after purchasing the skirt, I got it in my head that it was too dressy for everyday wear.

Over this last year of blogging, I have learned from 1930s starlets and modern-day fashionista friends that “dressy” is a relative term. Dressy pieces can be combined with casual styles to create personally expressive looks that transcend specific occasions.

Fashion for Science

In an attempt at convincing myself to keep the skirt, I put together a science experiment of sorts. Below are three different outfits pairing this skirt with more casual counterparts. If I like them enough to wear them often, I may just keep it. Take a look for yourself and let me know your opinion–keep it or delete it.

Outfit 1: Warm Winter Day

For this first outfit, Little Miss Houndstooth got casual with short brown booties, nude hose, and a peach-colored J.Crew sweatshirt I thrifted on Thredup.

Wow–quite a serious expression for such a casual outfit! Ignore my expression. Not sure what was going on there.

Out of everything in this outfit, the peach sweatshirt gets the most use. It is my “hanging around the house, running downstairs to get the mail, hopping across the street for coffee” shirt. (In fact, as I write this, I am wearing this very top!) It’s lighter weight than most sweatshirts I’ve owned and the peachy color makes it feel a little less casual than a regular gray sweatshirt.

Though I was unable to find this exact style anywhere, J.Crew carries several sweatshirts that are pretty adorable and not exactly “sweatshirt-y.” Click the photos below to follow the links, or click here to look for thrifted versions on eBay.

The jacket is from the same Zenobia family as the skirt. It doesn’t get worn much either because it’s made out of real shearling and I fear Seattle rain ruining it. I need to get over that fear and just wear the darn thing. It’s super cozy and I love it.

Similar styles like this jacket can be found on Etsy and eBay. Below are two favorites from Etsy. Click the photos to link to the jackets.

I added a vintage beaded collar from Etsy as a way of sparkling things up a bit. Like the skirt and the jacket, it doesn’t see the light of day much. It’s fairly new to me but I rarely gravitate toward it when I choose accessories. With the new year, I’m making a pledge to wear this more often!

If you like this kind of collar, you are in luck! Etsy is jam-packed with similar styles from the 1950s. A lot are still in great shape. Here are two of my favorites:

The booties are from another brand I rely on for winter footwear–Aquatalia by Marvin K. They can be pricey, so I thrifted these on eBay. To search for your own Aquatalia booties on eBay, click here. For new Aquatalia styles, visit Nordstrom here.

Outfit 2: More errands, but with a scarf

This outfit isn’t much different from the first one. I switched the nude hose for brown tights and the J.Crew sweatshirt to an Eileen Fisher tee.

I also put away the beaded collar to add a beautiful handmade scarf. The scarf was designed by “Amy Amy,” a friend of mine here in Seattle. She sends her designs to family and friends in Ethiopia and they hand-weave them from cotton. She has quite a few designs but doesn’t have a website yet. If you’re interested in purchasing one of her scarves, contact me with your email address and I’ll connect you with Amy.

Outfit 3: Casual, cozy, warm

The sweater for this outfit is Eileen Fisher. It’s about half the age of the skirt. I live in this cardigan during the winter and never thought before about pairing it up with the skirt.

Eileen Fisher doesn’t have a beige cashmere cardigan available anymore, but there are plenty of other retailers that do. Hover over the images for more info and click the image if something strikes your fancy.

I added a pair of Jambu boots to this look as a way of warming it up even more. If I thought I might be outside for long, I would add a warm scarf around my neck. Warm feet and a warm neck go a long way in keeping the winter chill out.

This exact style is available at Amazon for about $50. Click here to check it out.

As for the Skirt

Now that I’ve taken the time to find things in my wardrobe that go with this skirt, I’m leaning towards keeping it. There are other combinations I want to try with it as well. Who knows, maybe I’ll start wearing it all the time now. But I’d still love to hear your thoughts.

For those in the market for a houndstooth skirt, take a look at what my good friend and fellow fashion blogger, Suzanne Carillo, has to offer in her Etsy shop.

Macy’s has quite a few versions as well. Click the photos to shop these skirts.

Do you have a houndstooth skirt in your closet? How do you wear yours?

Affiliate link disclaimer: Please note, some of the items linked may be affiliated with companies I am associated with. By clicking the affiliated links and purchasing from those stores, I might receive a small commission. By purchasing from these stores, you support the work I do here and I greatly appreciate your support!

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  • My goodness but you have a nicely crafted blog! The picture of rhe gentleman in the houndstooth plaid suit is remarkably unusual! Who knew that men of the 1800’s had such flair?!! I love your comment, “WOW!”
    I say keep the skirt. The quality alone is difficult to replicate! You have invested some time and energy into styling it and the small scale plaid suits your petite frame. It’s a classic, as you said. I think it has more lives and I’m sure you’ll get interesting styling suggestions. How about some pattern mixing? A newsboy cap? Over-the-knee boots?

    • Thank you, Jude! I love your ideas and am going to give them a try before I give this skirt up for good. I hope you’ll weigh in with your thoughts once I post about this again!

      – Sherry

  • I agree with Marilee. It is too good to toss. Just the fact that you’ve hung onto it for this long means something. It is a very classic look and that may be what is throwing you off since most of your looks lately are a bit more quirky.

    I think look #2 is my favourite but that may have to do with the fact that you look happier wearing it.

    Unless you’re caught in a massive downpour I would think that shearling should be okay in light rain.

    I’m loving those last boots you showed! They look like I might be able to wear them during our winter and still be a little bit fashionable.

    I really like your vintage collar as well. You’re finding all kinds of treasures lately!

    Thanks for the shout-out lady : )


    • You’re right that hanging onto it for so long means something. Everything else in my wardrobe that isn’t related to this clothing line was given away or sold a long time ago. My rule is, if I don’t wear something for a year (two, tops), it goes. So this skirt is the real exception. With all the comments I’ve read so far–the ones that say I should keep it–I’m getting ideas for how to pair it up with other things in my closet. So, I’m going to give it another season and see how well I do.

      The boots would be perfect for Toronto winters! And did I mention they’re vegan? 🙂

      I will always include your shop in my posts when I can find equivalents to the theme I’m writing about. Since I own several pieces from you, I know the quality you look for and that’s nothing to sneeze at! Plus, I want to see you succeed and anything I can do to make that happen makes me happy.

      Can’t wait for February!!

      – Sherry

  • I mean, how many of us can say they can still fit into a skirt from 16 years ago….just for that fact, I think you should keep it!
    But seriously, it is totally a classic piece, Sherry! I think part of us wearing things, is a habit and finding out what we love about it!
    And I think you’ve gotten a great start of trying it out with different items!!!
    I love that sparkly collar with that sweatshirt—at first, I thought it was part of the item, but how perfect that you could pair it with other shirts!!??
    And really, this skirt would pretty much go with all the other tops you paired with your other plaid bottoms in the collage! Especially my fave one (the face graphic)!!
    My 2 cents? But a pair of OTK boots to pair with it—the skirt is just short enough that you can show off the boots!!

    • Thank you, Jodie! I am leaning toward keeping it for just one more season to see how often I wear it. Writing this post put a spotlight on just how long I had been holding onto it and, like Suzanne said, it must mean something. I never keep anything I haven’t worn for that long, especially now that I live in a much smaller place and have less storage. So, I’m going to try some of these ideas you ladies are posting and see if I can breathe new life into it!

      Oh! I have another top to try with this skirt that I think you might like. It’s from the same designer as the face graphic top. I’m planning on doing a follow-up to this post with some of the ideas you all have shared. I’ll include that when I do!

      As for OTK boots, I think that’s an excellent idea! The only problem I’m having is finding ones I’m willing to invest in. I love the look, especially with skirts like this, but I haven’t found any that just stand out and say “Must Have.” I’m going to try this skirt with some knee-high boots I got recently but will keep looking for OTK ones because I agree with you–I think the right pair would be great with this skirt!


  • I really like the skirt, and I think you look great wearing it! I think it truly goes with “anything,” and the three ways you styled it are very nice. And I’m sure there are more. I would definitely keep it! You could even come up with a little challenge and see how many different ways you can style it (and actually wear it “in real life”)…

    Happy New Year!

  • I say delete! {If Suzanne is reading this, she’s eye-rolling me right now, LOL.}

    But, here’s the thing…well…here’s my thing. If you’ve only worn this skirt a handful of times over sixteen years, I just don’t think you’re feeling it. You are clearly a master at the mix….vintage with modern; dressy with casual…I mean, you’re demonstrating your mad skillz right here, right now. You really do look fantastic in each of these looks! But. Huge but. I just get this spidey sense that you don’t feel quite your sparkly self wearing this skirt. And…what’s the fun in that?

    I’m clearly in the minority here….so don’t make a rash decision based on my opinion. I get things wrong. A lot.

    • Sue, your comments are the perfect balance to those who say keep the skirt. You hit right at the heart of reasons why I haven’t worn it much in 16 years: I don’t “feel quite my sparkly self” in it. That’s really true! When I bought this skirt, I was a little heavier in the waist area. I lost weight several years ago and now it doesn’t drape the same around the waist. It’s not that it needs tons of altering–it just hangs lower on my hips now, which feels weird. I don’t think anyone else can see it, but I can feel it and it bothers me when I go out wearing it.

      Having said that, I’m going to give it one more season, but only if I actually find pieces to wear with it that make me feel sparkly.

      You are my witness: If by summer I haven’t come up with 5 new ways to wear this skirt, it goes. And I promise to be honest about how many times I wear it off-camera as well!

      So, thank you for being honest and sharing your thoughts. You nailed a feeling about all this that I hadn’t been able to tap into until now.

      – Sherry

  • OK, I’m going to weigh in here because it’s my idea (just kidding. I love these kind of posts!) I look at it and go “bleh”. It looks corporate. It seems like a really generic plaid. It is gray and the pattern is uninspiring and you have so many other great skirts. You have a much more quirky style and this skirt blahs everything out. Feel free to disagree with me since I’m in the minority of your comments but like the top I asked my readers about, I got rid of it. If I haven’t worn it in two years (let alone 16) there is a reason. Delete it! Though everything else looks great as usual!

    • Hey Julia!!
      I totally get your reason to let the skirt go! But I’ve had times when the reason I haven’t worn something is because I get out of the habit or just don’t know what to style with it. Now don’t get me wrong…I’m all about purging items! But I have to admit, there are times I’m glad I hung onto something that gets rediscovered!! Like the gold bolero I’m wearing in my latest post. I almost got rid of it because I just couldn’t imagine how to wear it especially in the winter. Luckily, I played around with it enough, that I grew to love it again!!!
      It’s so fun to hear what others think and how they come to their decisions!! I’m so glad you were the inspiration for this idea!!

    • I love this idea of asking readers to help weigh-in on this, Julia! Thank you for the idea! You have such a fun blog. Even though I’m not the best commenter, please know I am reading your posts, loving your looks, and appreciating all the Detroit-area backgrounds. (My husband is from the Detroit area.)

      Your word “corporate” is so true! There’s actually a matching jacket that goes with this skirt, but I feel wearing them together is WAY TOO MUCH houndstooth. Ha ha! I see exactly what you mean, though. It is pretty straight-laced compared to most other things in my closet.

      Some of the other commenters have given me ideas for styling it and it’s inspiring me to give this just one more season. I want to see if I can push this to the next level–take the skirt from “corporate” and turn it into “quirky/fun.” But I would love for you to be a part of the group that holds me accountable. If you don’t see this skirt pop up in posts at least 5 times between now and summer, it goes! As I mentioned to Sue in a comment above, I will be honest about how often I’m wearing it off-camera as well.

      Thank you for everything, Julia — for your idea, for your honesty, for taking the time to comment. Maybe we can meet up the next time I’m in Michigan!

      – Sherry

    • Thank you, Zuma! I have decided to give it one more season and have taken the interest, excitement, and ideas from ladies like you who commented as motivation to make it work. My goal with it now is to post 5 more times between now and summer using this skirt as the base. I hope you’ll check back and weigh in on the results!

      – Sherry

  • Hi Sherry,
    I’m wondering if you have posted anything since this one?
    I just read your poem about the tree. I loved it.
    Hoping to get to know you a bit more before the meet-up in February.
    I’m not on Facebook or Instagram .
    Guess I’ll just satisfy myself with earlier posts on your fashion blog.

    • Hi Marilee! I haven’t posted anything since the skirt post, but I am working on several other things at the moment with hopes of posting more regularly this year. Thank you for your interest and kind support!!