Under $1 Per Wear: Timeless Pieces I’ll Always Love

The wardrobe staples that have stood the test of time — worth every penny.

Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you.

Some might say that I am a frugal person. Given how much time I love to spend watching Target hauls and cleaning montages on TikTok, drooling over activewear, mops and sweatshirts, I’m not sure that’s always true down to the core, but there is one thing I know for sure - I LOVE to get a ton of use out of the things I DO end up spending money on.

I have a “cost per wear” spreadsheet (are you surprised after my Thanksgiving post?) for a lot of my bigger purchases that I was on the fence about so that I can reflect back later and determine whether it was really “worth it” or not. The best recent example I have for this is my Peloton bike (my cost per use is now down to about $2 per ride - I’ve taken about 600 rides on it, though you also have to factor in the yearly membership fee, but that also covers other things, and it gets a bit complicated, but you get the gist).

I don’t have every item of clothing from my closet entered into a spreadsheet (though honestly, that sounds kind of awesome, doesn’t it? No? Just me?) I do have a few items that I know have stood the test of time simply because of how long I’ve owned them and worn them consistently throughout that time. I thought I’d share them in case you are looking for “those” staples in your closet. The ones you can justify spending just a little bit more money on because you KNOW you will wear them a LOT and for FOREVER. All of these items are down to less than ONE dollar per wear.

To kick things off, let’s go with a seasonal must have during the chilly months of January and February. A coat! I bought a North Face jacket to go skiing back when we lived in Chicago. While I can’t recall the exact date of purchase, my estimate is somewhere around 2012. Here’s a photo from my Facebook memories of me wearing it in 2014.

I still wear this very coat to go on my wintery morning walks with Waylon. Just wore it yesterday, in fact. (Sometimes I even still wear that exact scarf, oddly enough!)

I’m so glad I didn’t get rid of this coat when moving to the “warmer climate” of North Carolina. Of course, the winters here are a lot more mild, but we do still have the occasional cold snap AND now that I’ve been here for a decade … I’m much wussier about the cold we DO face. The other nice thing about this coat is that it is water resistant AND it has a hood, so I can wear it for rainy walks for extra protection - my rain jacket is very thin and really designed for spring weather. It also has two layers - you can zip out of the shell for a windbreaker layer OR wear the inner shell for more of a “fleece” type jacket. It’s extremely versatile.

While North Face does not make this exact coat model anymore, it’s safe to say that I think the North Face brand holds up over time and through consistent wear (and washing!). Here’s the most similar option I can find available from the brand now:

BUY: Women’s Insulated Jacket, $320

My Cost Per Wear to Date: 50 cents

On to a slightly less intense jacket layer.

You might be able to spy it in the first picture posted … my Patagonia Better Sweater (Buy it on REI for $110! You won’t regret it). After hemming and hawing relentlessly over this purchase (I was in my 20’s and $100 seemed like a LOT for this item of clothing), I bit the bullet and bought one. When I tell you it has been one of the most worn items of clothing in my closet, I do not exaggerate in the least. So many times when a memory pops up in my Facebook history, I AM WEARING THIS JACKET.

At a Blackhawks game.

Petting exotic animals.

Hugging Dan near the ocean.

Anyway, you get the point. It’s a great layer! It works in many different climates and with various items above or below it. It’s a great packing staple because you can either wear it for comfort WHILE you travel, or pack it in your suitcase - it will still look great whenever you arrive at your destination! I got grey, so the color goes with anything and everything. I am also honestly amazed at how well the quality has stood up over time. I do NOT put it in the dryer, but I have washed it plenty of times in the 17 years I have owned it. I still wear it constantly to this day.

BUY: Patagonia Better Sweater, $110

My Cost Per Wear to Date: 5 cents

Another staple I’ve been wearing pretty consistently over more than a decade are one specific brand of jeans: 7 for All Mankind. Due to a healthy obsession with Rue La La and the environment where I worked from 2008-2010, I acquired several pairs of jeans from this brand that I still. Wear. today. In case anyone doesn’t feel like doing the math … that’s 15-17 years. Now, given that I’ve grown and birthed two humans, there have been periods over that timeframe where I have been unable to fit into said jeans. But here we are today, back at it.

From this company, I have skinny jeans, flared jeans and bootcut jeans. BTW, very exciting news - I heard from a fashion TikToker that 2025 will be the year skinny jeans OFFICIALLY make a comeback! This is great for me, since I never stopped wearing mine even when they weren’t en vogue. I paid a lot of money for mine and I’m gonna wear ‘em! It’s safe to say that I’m not really in the market for too many pairs of jeans (I still have four pairs of this brand in my closet that I wear almost on a weekly basis), but if I was, I know this brand would be a safe bet for the long haul. I DO put these bad boys in the dryer, and even after almost 20 years of washing and drying them, they still look amazing. You can actually check them out in the lemur photo above - I’m wearing a pair there! I’m wearing the skinny jeans in the photo below as well (AND my Better Sweater, again!).

BUY: 7 For All Mankind Skinny Jeans, $198 OR Bootcut Jeans, $228

My Cost Per Wear to Date: 30 cents

Back to cold weather layers. On a bit of a whim, I bought a red puffy vest from a Gap outlet store in the year 2000. That’s right, folks. I have owned this vest for 25 years. That’s 10 years longer than I’ve been married. That’s OVER HALF OF MY LIFE. And I still wear it all the dang time. I just wore it as my “red” for the black and red colors of the Charlotte Checkers when we went to the hockey game last Sunday.

Gap still sells a vest similar to this, but I think honestly, the lesson here is that vests rule and you can get a LOT of use out of this layer. Honestly, if I were to replace this puffer vest today, I would probably get one from North Face.

BUY: Gap Vest, $44 OR North Face Vest, $150

My Cost Per Wear to Date: 25 cents

My last recommendation is something that is currently trending (again) for probably the third time in my adult life. UGGS! I’ve always been a fan of these, because I tend to prioritize comfort over almost anything else (see: my addiction to sweatshirts and my new sweatpants). But, every time I’ve owned a pair, I wear the everloving crap out of them and they HOLD UP over time. So I will never be sorry to have a comfy pair of Ugg Boots to slide my chilly tootsies into for carpool pickup in the afternoon. My most recent pair are gray minis that I got as a Christmas gift ten years ago, and I still wear them almost every day during the fall/winter seaons. You can see them in the above skinny jeans photo and also on my feet almost every day right now.

BUY: Ugg Classic Ultra Mini Boots, $150

My Cost Per Wear to Date: 75 cents (though since they were a gift, technically it’s nothing, but IF I had paid for them … )

There you have it! My top clothing staples that I recommend simply because I’ve gotten SO MUCH use out of them that I have gotten the cost per wear down to under a dollar.

Not listed above because no one else would ever be interested in buying them, the oldest/most worn items of clothing in my closet are actually:

-my senior year tee shirt from high school in 2002

-two Chicago Bears hoodies I got as Christmas gifts in 2009

-a Forever21 skirt I bought for under $10 in 2005

-Black Adidas flared sweatpants I bought from an outlet mall in 1999 (still wear these ONCE PER WEEK on my walks with Waylon)

-a gray Target-branded cardigan I found in the bathroom of a bar circa approximately 2008 (still wear this all the time, actually)

-a pair of these SmartWool hiking socks

-a Black Sabbath graphic tee I bought from Delia’s in college

Tell me - what’s the oldest, most loved, most worn thing in YOUR closet?