My Boomer Gal Pals Keep Me Feelin’ and Lookin’ Good

Whimsical Old Lady - Etsy Canada
My loyal circle of girlfriends is always on call when I need fashion prompts.

As we age, we can be tempted to lose interest in our appearance. Who cares whether our nails are done, our roots are showing, or the hair on our legs is long enough to style? No one sees our bare legs after Labour Day anyway. The extra hair keeps us warm in Canadian winters.  My husband has seen me at my worst, so who am I trying to impress? Sometimes, I make quick trips to the store, with no attempt whatsoever to put my best foot forward in public. In baggy track pants and my dog-walking jacket, wearing no makeup, it all seems perfectly acceptable compared to how some of my fellow shoppers are turned out—in sports bras, leggings with full camel toe on display, and fuzzy slippers.

Thanks to a tight circle of wonderful girlfriends, however, I have a built-in monitoring system to keep my wayward ways under control. My friend Margaret compliments me whenever I turn up at a lunch or dinner properly made up—like in my working days—with the full complement of eye makeup, foundation, blusher, and lipstick. She generously acknowledges my efforts and appears impressed that I took the trouble to look good—as if it’s an anomaly! Gail is delicately passive-aggressive when she asks, “When are you getting your hair done?” to remind me I’m due for a trim and new highlights. All my friends are so thoughtful that way.

COVID brought out the best and the worst in us. While we tried to be good citizens and support our communities, our mass retreat from the world was not necessarily a good thing. We couldn’t get to our regular mani/pedi appointments and hairdressers, or do mall runs. Our personal appearance became less of a priority, and many of us remained stuck in a state of apathy when the world returned to normal. Even though my efforts are pretty much back on track, I must admit I am often lazy about how I look in public, and certainly around the house.

When I retired, it was a relief to no longer be bothered each morning with layers of irritating mascara, liner, and various combinations of contouring eyeshadow. I now boldly expose myself to the world with a naked face and less-than-perfect hair. I stopped subscribing to Vogue, ELLE Canada, and Toronto Life Fashion magazines. I checked out. As a result, many fashion magazines went bankrupt. My apologies to all.

Clear Out Your Closet Clutter | Rug Doctor by BISSELL
Keeping our closet current and organized is an important part of avoiding fashion ruts.

I have not completely given up, however. My print magazine addiction has been replaced by Instagram, Pinterest, and YouTube. Even though I may not always look my best, I still have a strong interest in fashion. I’ve weeded out most of the duds in my closet, and I’m experimenting with new brands that suit my retired old-lady lifestyle, while still trying to look somewhat hip and on-trend.

I bought a pair of barrel-leg track pants a couple of weeks ago that make me look at least forty pounds heavier than I really am—not exactly a confidence-builder. The upside is that they are incredibly comfy for watching television and sitting at my desk. It’s like walking around in an insulated pup tent. I’ve even ventured out to the grocery store in them a couple of times, careful to avoid anyone I know.

One of the major problems with current fashion is that it’s not designed for 5’2″ retired boomer gals with a 27″ inseam and no defined waistline. I’d love to own a pair of khaki or camo cargo pants, but they’re only flattering on tall, willowy millennials. I’ve tried disguising my middle with longer sweaters or shirts, but the fashionistas tell me I should wear shorter tops to address the two-thirds-one-third rule of proportion. Sheesh! It’s so hard to get things right.

I’ve been trying new brands like Uniqlo with some success. Unfortunately, most of their pants require chopping six inches off the legs to fit me, and then the proportions are all off. Uniqlo has an excellent selection of quality underwear and basics that have filled the gap left by Hudson’s Bay going bankrupt—again, probably my fault. About once every four or five years I manage to score a pair of jeans at Gap that actually fit me, which miraculously happened last spring. But it requires endless reconnaissance trips to the mall, trying on more styles than I have the patience for. My go-to brand, Not Your Daughters Jeans (NYDJ), has always been hard to find in Canada, but it’s impossible now that Hudson’s Bay is gone. And, as we all know, jeans cannot be ordered online. They have to be tried on in person because fit and sizing are so unreliable.

For extra-special occasions, I may even wear a bra, which is a really big deal because bras are Satan’s work and I hate them. Skinny jeans have given way to whatever-the-hell shape you want, which is a good thing, but balancing proportions with the right top can be complicated. Skinny jeans had those of us with no waistline looking like tottering red-wine goblets. Comfortable shoes are de rigueur for boomer gals. Fortunately, there are lots of cool styles and colours out there these days, and I have more than I can comfortably justify owning. I particularly like Vionic with their industrial-strength arch supports.

Makeup Organization Ideas: Eyeliner - Makeup and Beauty Blog
You can never have too many eyeliners – right?

I ordered a new Clinique eyeliner online last week (still in search of the elusive perfect one) to add to the dozens already in my eye makeup boneyard that I never wear. You can’t accuse me of not trying. Just don’t make me go to Sephora and suffer the crush of teenage makeup groupies and 20-something, perfect-skinned sales staff, only to find out they don’t carry what old boomers need. Now that the last department store that carried beauty products has disappeared (Hudson’s Bay), no one carries the full line of each cosmetics brand, not even Sephora. I miss the full-time department store cosmetics brand sales representatives who really knew their product lines.

The next time I see my friend Gail, she will be thrilled that I finally got a haircut and new highlights.  I try to get a mani/pedi once a month, mostly because it’s getting too hard to get down there and do it myself. Ugh! The other day, when my friend MaryAnne complimented me on the blusher I was wearing, my mind immediately snapped to, “Am I wearing too much?” When my friends speak, I listen. Margaret lives two hours away, so she is generally spared from seeing me without eye makeup. When we do get together, I make the effort, so she’ll still be my friend.

Girlfriends are the staff of life. They have been there over the decades to discreetly remind us when our slip was showing, if there was a run in our nylons (remember those days?), or when we have lipstick on our teeth. If we have family problems or are feeling fragile, they lift us up and keep us strong. They help us get over ourselves, repair ourselves, reinvent ourselves, and celebrate ourselves. Are your friends as supportive as mine? Will they tell you when you need to swap out that unflattering lipstick? We stay beautiful with a little help from our friends. Feel free to comment below.


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2 Comments

  1. MaryAnne 17 October 2026 at 12:40 pm

    i’m with Margaret. When you walked into the restaurant the other night you were just beaming. Wearing makeup makes us feel good. That little smile when we put on our lipstick just before we go out the door says it all. Wear your makeup.. And no, you were not wearing too much blush. You were perfect. But, I’m still wondering why you didn’t tell me to get my haircut shorter🤷‍♀️

  2. Anonymous 17 October 2026 at 10:29 am

    I agree, girlfriends are priceless as we keep each other in check. Trying to keep ourselves dressing age appropriate but not dowdy is not easy without these fashionistas.

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