Is “Investment Dressing” Your Jam? We Break It Down

I’ve read lots of articles about “investment dressing”, using cost-per-wear to determine if a clothing purchase is a good value. The basic idea: even if an item is expensive at purchase time, repeated wearings bring the actual per-wear price down to something reasonable. The Budget Fashionista has a nice simple explanation here.

{For us math-challenged shoppers, here’s a fun calculator to speed up the decision making — The Glamour Cost Per Wear Calculator.}

Yippee, I love to analyze!  So here’s my take on cost-per-wear (CPW), or investment dressing – the concept is valid for certain categories of clothing:

A serious handbag is worth a few dollars IMHO. Handbags are such a personal choice, though, and you can rotate through lots of fun, inexpensive bags in a year for the price of one “good” one.  It’s hilarious to apply CPW to a super-high-end handbag. Here’s a fetching one for a cool $6,500. If I wear it 7 days a week for 5 years, that’s only Three And A Half Bucks a Day for my handbag! But . . . I know I’ll never want to wear the same bag every day for five years, will you?

I could carry this rich leather tote for a long time, though.

So Question #1 for you, Do you prefer variety, or one/two higher-end handbags?

Shoes are a no-brainer for me — my 60+ year-old hoofs can’t tolerate cheap shoes anymore. And a great-fitting pair results in an attractive cost-per-wear for me, because I will wear them to the nub, and keep them for years. I’m not talking about Louboutins (but I love these!) for my modest life, but a new pair of Soffts, Dansko or Indigo by Clarks and my feet/wallet are happy. The math works.

Crazy about these booties from Dansko.

Question #2 – What’s the oldest pair of shoes you own and still wear regularly? Mine are probably my funky Cydwoq booties.

A couple of cashmere sweaters and a high quality coat are other items I’d permit myself to spend a bundle on. Cashmere lasts for a long time and keeps its good looks, if washed carefully. A killer coat or jacket will do me for a decade in Florida, and makes any winter outfit look more special.

If you like a non-traditional coat, here is a beauty.

Everyday pieces — cardigans, shirts, knit tops, skirts, jeans, et al — I just can’t spend too much on these and justify it with a cost-per-wear. Consignment and thrift shopping have spoiled me for full, high-retail on these pieces. For example, I’d have to wear this beautiful skirt about 120 times to get it down to a comfortable CPW of $2.50. My lovely floral thrifted skirt gets the job done in five wears.

After handbags, shoes/boots and coats, the “investment” paradigm starts to lose its power for me. For example, in my corporate years, I used to think suits should be purchased with the investment philosophy. But I never really did get my money’s worth out of the wicked expensive ones. The styles changed just enough that I looked dated, or I got tired of the cut/color long before the CPW was reasonably low.

What’s your take on cost-per-wear and Investment Dressing?

Enjoy every day, and stay fabulous, xo,


Here’s some fab pieces to browse:

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  1. I paid $100 for a bag from Winners several years ago and at the time it was the most I’d ever spend on a bag, I carried it every day for years, and it’s still going so it was definitely worth it. I have spent a lot of money on shoes, and sometimes it pays off, and sadly, sometimes it doesn’t. For the most part, I don’t think about CPW.

  2. For me Patti I agree about cheap shoes!
    I try and find cheap expensive shoes.
    Scouring online sales, eBay and charity shops to find what I want at a price I like… ditto cashmere!
    I’d love a big budget (dream on!!) and if I had one I’d spend it on a few pieces of cashmere, a good wool coat, leather skirt and skinny leather trousers, quality shoes and boots, a beautiful chunky piece of jewellery and a fabulous bag.
    In the meantime, I’ll enjoy my thrifted pieces and dreaming!
    Merry Christmas to you and your family Patti!

    • Merry Christmas to you as well, Samantha! You enjoy the hunt for great stuff at a good price – I do that too! xox

  3. I never pay full retail for anything ” investment” and that thinking has paid off with a 750.00 Longchamps bag that I scouted on line during a Black Friday sale. It’s from their unusual Cody collection and I got it for 250.00. It’s investment sure but practical and I won’t see it EVERYWHERE! Also a pair of Aquatalia tall suede boots ( retail 725.00 for 245.00) both will give me years of wear and enjoyment. What I’ll pass on are the over priced, over hyped Eileen Fisher pants. Ah I work, I need more than one pair of pants and can get better quality at better prices from other sources. Also cashmere. It doesn’t last all that long so if it’s not on sale, pass. Case in point two great cashmere sweaters from the The Shopping Channnel ( of all places) for 75.00 each! Compared to a pricey 175.00 sweater ( on sale:( that has pilled and stretched and gets worn with jeans. The two cheaper sweaters are older and still look fantastic!
    I also watch trends and shop Amazon, manufacturer web sites ( much better prices then retailers) and ( sorry Patti) totally avoid Shop Style links unless I am being lead to a super sale. You can have an awesome wardrobe with a few killer investment items if you put the effort into it. As one becomes savvier and choosier it takes less time!

    • The tall suede boots sound dreamy! Thanks for coming by, and happy holidays to you, xox.

  4. I have never thought of the cost per wear before this reading this post. The most I have ever paid for a pair of shoes was $85.00, this past August, when I bought a pair of Under Armour tennis shoes. I went to Road Runner Sports with my husband who buys 2 pair of shoes there, every 6 months or so, and then walks them over a hundred miles a month to keep in shape. I have never calculated the price per walk but the almost $275.00 he spends for two pair of shoes is most likely down to pennies by the time he tosses them into the recycle bin. My Under Armour shoes were a great investment as they feel wonderful on my feet and I love walking in them. I have begun to walk more myself since the purchase. I usually buy Walmart tee shirts and jeans.The Tee Shirts last about as long as I like them and the jeans are actually good quality and last a nearly two years. I am rough on clothes so I don’t want anything too expensive. But just last week I ordered from Romans and my purchases came today. The quality is much better than Walmart and the price was not that much higher considering the sale they were having. I will most likely be ordering from them again. When it comes to purses I have never paid more than $35.00. I usually use one purse till it falls apart. One of the best purse purchases I made was at a wonderful Thrift shop in Oceanside, CA. It was $10.00 and I used it till it started to tear and the fringe on it was falling off. I still have it in my sewing room. I am thinking of using it for a pattern. Until now I don’t think I would have ever thought to calculate price per ware. I just buy what I like at the price my budget will bare.

    • Thanks for commenting, Sue. The fact that your comfortable tennis shoes make you want to walk more is high praise! xox

  5. My problem is that sometimes good quality shoes (including brand names mentioned) aren’t as comfortable as I would like! It’s hit or miss for me, unfortunately.

    • Hi Rebecca! It’s true, sometimes we can score inexpensive, comfortable shoes (like Keds : >). xox

  6. Up until 10 or so years ago, I was constantly bringing back bags of crap from malls and ordering blithely online. Most if not all of that stuff is gone. What remains is the stuff I bought at boutiques and small stores, not super expensive, but better in quality, more interesting pieces that I chose thoughtfully because they weren’t dirt cheap. Now I have discovered how to find the good stuff in consignment, thrift, eBay and Poshmark. Smaller, better, more sustainable closet and I like all my clothes!

  7. Another great post!

    I work from home and live in a new city, so I know and see very few people but do enjoy looking spiffy when I go out. Designer/big name brands have never appealed to me and I do 95% of my shopping online. Citron of Santa Monica is one of my favorite clothing lines and Ebay carriers a lot of these items. A few years ago, I bid on and won a marvelous, midi length black Citron wool coat that is covered in gorgeous, bold embroidery. I wear the hell out of that coat in the fall, winter (lots of layers under the coat when it’s freezing) and spring even though I have a down midi and a shorter down jacket as well as leather and pleather coats/jackets. This coat was under $200 but it is a piece that I am stopped on the street over every time I wear it and just looking at it and donning it gives me enormous joy. I think I got my money’s worth the first year I bought it. I’ll pay a lot for an item of clothing that is unusual, one of a kind or soul stirring, be it a designer brand or a one off. At 66, life is too short to wear ordinary stuff, even if I am the only one who sees it.

    • So well said: “life is too short to wear ordinary stuff”! Your coat by Citron sounds beautiful, xox.

  8. I have a gorgeous coat that’s just classic enough and just unusual enough (kind of a Cossack style) to never be trendy nor out of fashion. I’ve had it for 20+ years. I wear it maybe a dozen times each winter, partly because it’s quite dressy, partly because it’s warmer than I usually need. But when I bought it I wore it daily in winter for several years straight. Definitely got my money’s worth.
    As you say, the suits show their age in style, not quality. But you can spot a cheap suit across a room, and if you want to compete with the big guys you have to dress the part. But it all depends on the industry and company you’re in.
    I had a Furla bag that lasted a good decade (and that didn’t break when a purse snatcher grabbed it and I didn’t let go in and got literally dragged down the street in Barcelona), maybe more, before it fell apart. Like suits, a cheap bag shows, but even an expensive one ends up scuffed and scratched no matter how careful you are, and eventually the handle looks pretty ragged. Nothing lasts forever. I aim for some happy medium of paying somewhat more for decent quality but not squandering a fortune.

    • Agreed, the happy medium is usually a good place to hang out! I’d love to see your Cossack style coat, xox.

  9. I think it depends on how you use CPW, since it’s a tool. If you’re using it to justify a big $ purchase (“I’ll use this bag every day!”), then it’s not a helpful thing. I use it more to amuse myself on how little some of my thrifted things end up costing – more for fun than anything else.

    I have used the same bag for at least 5 years! I paid $199 on sale for it, and it’s down to pennies, Patti! Ha!

    I spend on: eyeglasses, bras, sometimes shoes (Fluevogs!), and sometimes jewelry.

    • You win the handbag division! And you have awesome shoes. Heh, I don’t wear a bra, so imagine the savings! xox.

  10. It’s much harder for me with my fluctuating weight throughout the years—but, keeping that in mind, I tend to spend more on an item that ‘works’ for me, even if I know it may not be forever. Def shoes and eye-glasses!! Also, other functional items, like rash guards for summer or winter boots.

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