Most women I know have a love/hate relationship with their closet. Same goes for clothes shopping. We dream of a perfectly curated wardrobe full of stylish, comfortable clothes that we can select with ease when we need to dress for an event. We long for well-made, well-cut clothes that accentuate the good and downplay the not so good. We want to look effortlessly chic. Is that too much to ask?

It doesn’t help that as we age, most women deal with things like weight redistribution, loose skin and other mid-life body changes. Things that can’t be exercised or dieted away. These are the challenges of shopping for new clothes in middle age and the topic of today’s column.

Let’s start with a closet clean-up:

For many of us, the change of season signals a semi-annual closet flip/purge and refresh. A time to get rid of those closet strays, ill-informed impulse buys, pants that, let’s face it, will never fit right – along with tops that looked cute but don’t seem to go with anything.

I always start out with good intentions and lots of energy for my personal closet clean-out. I make piles. Piles to donate. Piles to bring to resale. Piles to decide… keep or pitch? I sort these neglected garments into shopping bags – destined for the trunk of my car.

Once my closet is sufficiently purged, I pledge to purchase only items that are flattering, fit well, work with other items in my wardrobe and are not overly trendy.

Ready, aim, shop:

On a recent afternoon spent at an outdoor shopping center, I hoped to find some of those aforementioned wardrobe gems. Instead, I encountered what can only be described as “shopping angst.”

Upon entering one popular women’s store, I flipped through a rack of tops wondering “is any of this me?” I selected what appeared to be a classic white blouse and immediately noticed that the bottom half seemed to be missing. I’d clearly wandered into the land of cropped tops.

I quickly put the half-blouse back and wandered over to a table stacked with Spring sweaters. They appeared to professionally folded, so I carefully removed my size out of the the middle of the pile. After unfolding the sweater, much to my dismay, I discovered that it was also missing its bottom half.

At the sales girls urging, I tried on a shift dress that hit about 10 inches above my not-so-toned knee area. The clerk exclaimed, “that dress looks GREAT on you!” I didn’t think a dress seemingly designed for a twenty something Instagram influencer was “GREAT looking” on this grandma. I was also suspicious that she was doing her darndest to move the merchandise. I stood my ground and passed on the mini-dress.

Sensing that this particular retailer caters to customers who, unlike me, are interested in showing off their midriff, I slunk out empty handed and moved on. The next store seemed tailored to “women of a certain age.” Alas, I didn’t find anything there either. I’m not young or svelte enough for cropped tops, yet I’m not quite ready for the drapey styles reminiscent of what Bea Arthur wore in “The Golden Girls.”

I’m in that “no-woman’s” land when it comes to fashion. It doesn’t help that I’m way taller than the average woman and especially “older” women. At 5’10” many styles are too short on me – and with the trend of cropped everything, I look especially ridiculous. My shorter friends lament having to roll sleeves or have pants hemmed. We are at opposite ends of the sizing spectrum.

Not being one to give up, I ventured into another store – and like Goldilocks, the third choice proved to be a winner. While this particular chain caters to the over 40 crowd, they have a stylish selection that works on a wide variety of body types. I purchased two pairs of linen pants and a couple of tops to coordinate. Success – at least for this excursion.

A topic worthy of discussion:

Get a group of women together and the talk will often turn to clothing. This is often instigated by a comment along the lines of “cute top/dress/outfit, where’d you find it?” The conversation often diverges into the challenges faced finding those compliment worthy outfits.

There’s a wide variety of views and preferences when it comes to shopping. Some women love perusing stores for hours. Others approach it as a chore – necessary but unpleasant. Many have given up on brick-and-mortar stores and do the bulk of their shopping online, taking advantage of free shipping and returns along the way.

Do we have too many clothes already?

Clothes shopping angst is certainly a first-world problem exacerbated by social media feeds that tempt us with fast fashion that is quick to buy, but once delivered to our doorstep, these styles rarely look as good or fit as well in person. They are often returned, or if kept, end up languishing in a closet with the tags still attached.

There’s also growing concern about the number of garments we discard.  Apparently, there’s a huge pile of abandoned clothing that can be seen from space! That alone makes me rethink adding to my own closet chaos.

Surely, there are ways to approach our wardrobe shopping habits that are better for both our psyches and the environment?

It would be great if more apparel manufacturers made garments that are well-tailored, timeless and durable. Clothes that we’d be likely to keep, and wear, for years instead of months.

I often find the stress of shopping, choosing outfits and fretting over what to wear, exhausting. I admire people who curate capsule wardrobes or have their own iconic style. Diane Keaton with her drapey earth tones. Or those billionaire-tech-bro’s who live in hoodies, jeans and allbirds.

Finding the latest trends, perfect fitting jeans or a stunning special occasion dress can feel like hitting the jackpot, but classic, timeless and well-made garments are the ultimate closet winners.