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.

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.

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.

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.

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