Fashion Dilemmas

150 150 Frances
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Dear Kristin,

Would someone please stop me from shopping for clothes at Kohls? I mean, I love the 30% coupon as much as anyone, but I never find anything there I really like. Kohls only seems to sell three kinds of shirts, none of them flattering. Not to mention the fact that when I look around the store mostly what I see is future landfill fodder. There’s just too much stuff.

The problem is, I’m such a lazy shopper that just the idea of spending a morning or an afternoon wandering through shops at the mall exhausts me. I’m cheap and easily overwhelmed, so I end up buying horrible things from the sales rack that make me question my sanity once I try them on at home.

I think clothes shopping is an art. My friends who dress well know how to shop. They know what looks good on them. They have the patience to look at a lot of different things and try on a lot of different things. 

Of course, the elephant in this room is the fact that my weight has fluctuated (sometimes dramatically) all of my life, and that means there have been shopping trips that have left me in the depths of despair. I can’t tell you how many visits to the mall have resulted in me rejoining Weight Watchers yet again. These experiences have scarred me for life. I’ve been at a good weight for the last year or so, and I’m starting to think that maybe I’ve figured out how to maintain it, but I fear it’s too late. Shopping will never be fun for me. 

The only decent shopping experience I’ve ever had is the time my friend Danielle went with me, probably fifteen years ago. Danielle knows how to put a look together. She knows how to accessorize. We went to Kohls, because Kohls doesn’t overwhelm Danielle (I also have the vague feeling that Kohls might have been better back in the day, but maybe that’s just the misty glow of nostalgia). I stayed in the dressing room and Danielle brought me outfits. She brought necklaces. She brought shoes. I was getting ready to go on a week-long book tour, so the pieces she chose for me were both professional and stylish. When I looked at myself in the mirror, a stranger peered back at me. A chic, well-accessorized stranger in flattering slacks and flowing, flowery blouses.

Jean Seberg, My Fashion Model

Sadly, Danielle has moved (though I’m sure with the proper enticements I could lure her back for another shopping trip). The fact is, I rarely need the kind of outfits like the ones Danielle helped me put together, and as lovely as those outfits were, I didn’t feel quite like myself in them. I’ve always liked an androgynous look–no frills, no pleats, no flowers. I’m most at home in long-sleeved L.L. Bean tees in navy blue and black, skinny jeans and clogs or boots. Throw in a cardigan sweater and some hoop earrings and that’s my look. My uniform. I’m never unhappy in this outfit. Everything fits well, so I don’t feel frumpy. I still wear a touch of makeup, still get my hair cut and colored on a regular basis. I stay as far away from frump as I can, but I never lean into fashionable looks.

Sometimes, though, I feel like I should try a little harder. You recommended looking for a cardigan in burgundy or red, and I like that idea. I can pop a little color if the occasion calls for it. And I love color! I make colorful quilts, love colorful flower bouquets, and colorful clothes–on other people. So I’m going to go in search of the perfect colorful cardigan–and I’m going to do it online. No more Kohls. And maybe no more malls. A few posts ago, Marsha H. made a comment that really resonated with me. “Just last month I made a long overdue trip to the mall for a little shopping,” she wrote. “I lamented to both my adult daughters (in their 30’s)…. just where do I fit in at this mall?” I’ve never felt like I fit in at any mall, a condition that may only worsen as the years go by.

P.S. Ordered the sweater!

Dear Frances

Why is getting dressed so hard? I’ve never found fashion easy, but like you, I’ve struggled with my weight most of my life and I have fallen into a trap of buying “temporary” clothes (hello Kohls!). I find myself not wanting to invest in the nice quality clothes I deserve, because I am hoping that in a few months, I’ll be down ten pounds, the clothes will be too big, and it will all be a big waste of money. Have you been there?

And on a related note, instead of building a wardrobe, I tend to completely wear out my small wardrobe, so I’m in the pattern of replacing versus building.

All that said, I think I’ve found my groove in the last few years. Funnily enough, it was because of the pandemic. But let me back up. About five years ago I came across the concept of a capsule wardrobe. The idea is that you focus on a few key colors that all work together. This was tremendously appealing to me. Gone were days of being a slave to whatever color palette The Loft outlet put together for the season. Gone were the days of wearing colors that didn’t suit me because were “in”–colors like spring green, orange, or purple.

I figured out that a few basic colors in bottoms like black, gray, navy, and denim all went with the colors that look good on me. For tops, I stick to pinks, blues, dark green, and burgundy. Throw in a few white, or even better – cream tops and suddenly it’s not so hard to get dressed anymore! It was a joy to purge all those colors that I knew didn’t work but had bought anyways. Packing for a vacation became less about putting together outfits, and more about figuring out how many pants, tops, and sweaters would get me through the allotted number of days. They all go together!

Back to the pandemic. Somewhere around month five of lockdown, I read a tweet that basically said, “If you’re still wearing jeans, what are you trying to prove?” There were options?! I was aware that a lot of people who were new to working from home were wearing pajamas or sweats all day, but I had been working from home for the last ten years and I always made it a point to get all the way dressed for work. Hair, makeup, and reasonable clothes. All I really had that fit the pants category were jeans. And skinny jeans at that! It never occurred to me that I could be more comfortable.

I was not going to slide into pjs or sweats for work, however. This is when I discovered linen pants. I’ve always wanted to capture that J. Jill vibe of flowy linen clothes, but it had never come together for me. As I’ve played around with this look, I’ve found some more affordable options. I practically live in Old Navy linen blend pants and have a number of linen and linen blend tops as well. There are a lot of good choices at Gap and Old Navy. I’ve found that shopping online gives you many more choices and the return policies are good. Because of the blend, they don’t wrinkle as much as true linen and they get softer every time I throw them in the dryer. Over time, I’ve put together a handful of pants in black, olive green, natural linen, and white, and I’ve even added a crazy for me pair of mustard yellow pants that still go with most of my tops and are a fun change.

For everyday footwear, I’ve almost entirely switched over to Birkenstocks (I’ve now got four pairs in various styles) and when I get dressed in some linen pants, a linen top, and some Birks, I’ve never felt more like myself! I can dress up appropriately when needed, but this is my everyday look.

At a Tuscany winery wearing my funky mustard pants and my Italian linen top

We recently went on a bucket-list family vacation to Italy and I was able to pack for the trip in a carry-on. Four pairs of linen pants and a variety of tops to go with them, everything from a basic t-shirt to dressier tops for dinner. I added a few sweaters to dress things up for evening and wore a denim jacket on the plane and had everything I needed. And I even came home with a linen shirt from Italy—linen seems to be everywhere there!

As the seasons start to change, it’s been easy to add a few pieces in my go-to colors to freshen things up or replace the t-shirts that wear out. I’m no longer replacing everything when I’ve worn holes in them, but finally, feel like I’m building a wardrobe that fits my casual lifestyle.

I aspire to upgrade a number of these pieces to better quality versions from places Boden or Pact, but it’s been fun to experiment and finally, at this stage in my life, find my style.

If you want to learn more about capsule wardrobes, check out The Well Dressed Life and Classy Yet Trendy for inspiration. I also love Dressed for My Day on YouTube for age-appropriate fashion advice.

P.S. Love the sweater!

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  • Susan from Ohio

    Kohl’s doesn’t work for me any more either. Not sure if it’s them or if it’s me. I also became annoyed at the Kohl’s Cash that I earned and then felt compelled to return to spend. Rather than feeling fun and like “free money,” it started to feel like gum on my shoe that I could never quite get rid of.

    I have discovered Stitch Fix which is now my go-to. It takes a bit to fill out the guide with your sizes and preferences. It also took a time or two for the stylist to send me pieces that I wanted to keep. But it’s such a relief not to have to go to the mall, that it’s been worth it to me. Five pieces come in the mail as often or as little as I want. I have a few days to try them on and decide if I like them. Then I pay for what I like and drop what I doesn’t work into the the prepaid envilope they provide. It’s undoubtably more expensive than shopping with the 30% coupon at Kohls, but it feels a little like a present when the box drops on my porch, and I get to take inside to see what’s been sent to me this time. Side advantage, with the “unboxing craze” that my daughter was caught up in, for a brief moment, she thought I was cool and would join me in opening the box. Now it’s become a FaceTime opportunity to spend time with my darling and always fashionable offspring who helps decide what to keep and what to send back. I’m willing to pay a little more for the convenience, and I’ll pay anything to have my daughter’s undivided attention for 20 minutes.


      Boy do I relate to Kohl’s cash being gum on my shoe that I could never get rid of! My husband just brought some home today…ugh. I have always wanted to try Stitch Fix, mostly because I know that it’s more expensive, but probably not when I factor in all the clothes that I buy that aren’t quite right. I’d love to have a stylist make suggestions! And bonus points for time with your daughter!

      • Mari Parker

        I so relate to this!! I yo-yo with my weight and found that with a recent weight gain, I had nothing to wear. Instead of buying a bunch of clothes I’m not happy with a week after buying them, I decided to buy a few good pieces from J.Jill. I usually don’t love shopping but brought my friend with me and we had a blast.
        I’m still hoping to kick off 20 lbs but in the meantime, I’m looking and feeling good.

    • Frances

      I love that you unbox with your daughter! I’ve looked into Stitch Fix but it’s much too stylish for the likes of me! Still, I’d love to see what they’d send!

  • Janet

    I enjoyed this conversation. I too find it challenging to find nice looking clothing. I am particular about how the fabric of the clothing item feels when touching it and also the cut of the neckline in tops. I like to look for items that are not mostly composed of polyester. It seems like polyester dominates the clothing market though.
    I would like to find out where people shop. My little town is limited in clothing stores.

    • Frances

      I do most of my online shopping at L.L. Bean (long-sleeved tees) and the Gap and Old Navy (jeans). I agree about the polyester–it’s everywhere!

  • Robin A Leftwich

    I’m not an in person shopper. Lands End is my go to. Now that I’m retired there is no need to shop. I always hated going to stores, maybe because I’ve always been big boned, not fat, but not skinny!
    It makes me proud that you are both stylish active women who have found your look and are happy with it!
    Kristin, thanks for the Italy picture. Your whole family is so cute, and your daughter in her hat is adorable!

  • Vicki Holloway

    I had a fashion revolution during lockdown and working from home, too. I decided that I would never, ever wear uncomfortable clothes. I found pull on pixie pants from Torrid. I bought 3 pair of these black stretch pants. They are pants not leggings, just knit. I decided I only wear knit tops and there are several pretty ones online from the same store, that are perfect for work. I know my size. This season I found some pull on pants knit with pockets and more shirt from my store. So, I bought 5 pair of the same pants and the top in every color and print they have. It is my uniform, yes. I am a Birkenstock person and have been for years. I have gained a few pounds over the last 3 years. These clothes are perfect for fluctuating weight too, and they wear like iron. I decided that as a woman of a certain age I can wear what I want, I don’t care if they meet the fashion standard for some as long as I meet my work dress code. Comfortable shoes are a must and not wearing painful clothes suits me just fine. I will never wear another pair of jeans again in my life!

  • Marsha H

    I have to dress up for work although over the last 10 years I would say our office has leaned more into “office casual”. I strive for a simple, comfortable but not frumpy style. At 60 I want to look like I care about my appearance but not that I’m trying too hard. Does that make sense? I lean towards lots of black with easy tops (must stretch-does everyone else do the reach test like me when trying on a top?) and cardigans. Cardigans camouflage lot of bumps etc. and protect me from drafty Midwest winters. Buy the cardigan, Frances! I think I have 8-10 cardigans! They’re easy to dress up or down for work and weekends. I’ve decided I’m sticking with pants from Loft and cardigans . . . many, many cardigans!
    Great blog, ladies! I so enjoy both of your podcasts and these blogposts are right up my alley. Love the notes back and forth concept-so clever!

    • Frances

      I know what you mean about trying too hard. That’s how I feel when I look at some of the “Women of a Certain Age” style blogs. It’s just a bit too much for my tastes. P.S. I bought the cardigan and am really looking forward to getting it. It will go well with all of my black tee shirts! xofrances

  • Audrey

    Such a fun blog, glad the two of you are writing about real life and real life “things”. I’ve never been a fan of all of the “coupons”, but have always found them hard to resist (you know, a woman and a coupon), anyway ever since we’ve moved to a small town and the closest Kohl’s type store is 45 minutes away, I find it much easier. (Smile)

    • Frances

      I know, right? If you have the coupon, you feel compelled to use it! Especially the 30-percenter! Maybe I should move 45 minutes away from Kohls too!

  • Patty

    My retirement “uniform” ….. I’m all about the yoga pant (Old Navy), tee shirts, and some kind of lightweight jacket from Target or even a hoodie! (Comfort rules!) When I feel the need to be less casual, I go with jeans, boots and pair one of my 2 nice shirts with a sweater.

    • Frances

      I keep three nice shirts in my closet for when Clifton and I are going out for a rare night on the town or I’m meeting someone I don’t know well. They don’t see much action, but I’m glad that they’re there!

  • Frances in Wales

    Oh, I am so stuck in the ‘temporary clothes due to intentions of impending weight loss (that hasn’t happened… yet!)’ trap.
    We don’t have Kohls, but my clothes shopping tends to revolve around discount days at the supermarket… Not exactly stylish or long term.

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