Synne, my style is feminine? Oh, horror! LOL
I like soft shapes and drape but don’t do it with an intention to look feminine.
I grew out my hair during Covid but recently cut it above the shoulders in a straight cut. I found that long hair is not for me anymore, it looked too wispy, weak and too girly on me. When it comes to a haircut, I search for what would work for my type of hair and my face shape. I do not like my hair but find it is an easiest thing to change.

We are sometimes our worst enemies. We tend to over analyze fashion, at least I do. True style, feminine or not is much simpler - wear what makes you feel happy when you look in a mirror. Repeat.

I like what MaryBeth said, too.

And I was also thinking, maybe, in some items, the opposite of softer. Maybe sharper tailoring again.

You look fantastic in a sharply tailored jacket and it makes you look more feminine rather than the reverse.

The trouble with that is (and I know it well) -- it's hard to do your groceries in a small city in a sharply tailored jacket. It's one thing to go out for drinks or something wearing one, but another entirely to move from work to grocery to hardware store. That's when you want to revert to sweaters. So then you lose the "sharp" element. This is a problem I have yet to solve. Pointy footwear can help but it feels a bit dated at the moment (at least to me) and doesn't work as well with current pants. So then what? Maybe structured bags (I don't even own one) or maybe -- who knows? Hmmmm.

You always look beautiful and feminine to me.

However I know the feeling you write about. My current obsession is with this pastel and brights designer Olivia Rubin who is from London I believe. It's kind of like she's taking the Lilly Pulitzer market and updating it. The pieces are all over-the-top feminine and I get so many compliments when I wear anything from her. If these colors aren't your thing, maybe there are some other colors you could explore.

I agree with Suz above… in my mind, I was thinking sharp tailoring with little feminine accents. Nothing too relaxed if you will. In my mind, Lisa, you’re a structured person. You stand up straight. Your hair, makeup and nails are coiffed. You’re sporty but not in a baggy sweatsuit kinda way. Ok

I love what Mary Beth said, and think she hit the nail on the head with her advice to not retreat into invisibility. Lisa, you certainly read feminine to me, but I think you are wrestling more with a feeling. Mary Beth’s comments reminded me of a conversation I had with my mother over 20 years ago. A friend of hers had just turned 70 and was having a tough time with it. Mama, who was well into her 70s then, turned to me and said, “Aging is so freeing. The older you get, the more you become what you already are.” I’ve never forgotten that. She was right, as she most often was. The truth of her words have really come home to me over the past few years. I’m 66, and my always pale skin is practically translucent now that my blonde hair is fast silvering. Yet I feel that sense of freedom that Mama talked about. I feel freer in ways that include dress but extend much further. Things look different; I look different. My interests have expanded, I am kinder and more tolerant of people’s foibles—and boy Covid has really tested that! Aging is a new landscape and I like it. I always did like a challenge.

I don't have much to add, except that I love the conversation this has provoked and agree with the idea that you may be able to tweak ("lean in") to your current style rather than overhaul to get what you are reaching for.

I am grappling with a related problem in an opposite way - I want my style to be a little more cis-masculine, or at least gender neutral. My curves and love of bright colors fight against that a bit. That said, I keep a large wardrobe so I have room to indulge different areas of the masculine-feminine scale, as my mood dictates.

Such interesting replies from all of you! Funny, but you've deep-dived (yes I know that's not a word) where I wasn't . I am interested in adding more feminine pieces to my wardrobe, more feminine colours, silhouttes, etc where right now there is little. My casual wardrobe is where this is really evident. Everything is neutral and basic, and feels like it could be interchangeable with my husband's if we were the same size. I have little latitude in my work wardrobe so there is not much I can do there. What is sticking out in my mind, after a few recent comments on the forum about the chunky boot trend , is my footwear. It's either all very gender-neutral (sneakers) or very standard with even my booties reading as basic .

The psychological part of it is easy to understand for most of us, by what I read here. And no, it's not a loss I'm feeling, rather an absence of something I've never invested in.

I wish replying to individual remarks was easier - and that losing text didn't happen when one scrolls back a page. But so much needs to be acknowledged here!

Sally - your comments are bang on. Sweatshirts aren't great with jeans and sneakers if one wants to feel dressed and somewhat pretty. But what the heck else do you wear at home ? I agree that t-shirts and shorts , or even t-shirts and jeans aren't a great pairing - and I've moved away from that for summer dressing. Winter - not so easily. Introducing blues is a great idea though - I own almost nothing in blue other than blue denim. Black is so tiresome because I have to wear it everyday, and pairing it with olive and grey is about the same. Thank you ! You've been very helpful here!

Irina - I see you as uber feminine because of your hair and eyes (what little we see of them , anyways, haha) and the ease with which you wear your clothes . I agree with less styled hair - it's my goal to get there as I hate sprayed and styled looking hair too. And yes to less chunky shoes! They are all of a sudden everywhere and in every price range - so that the special-ness has gone. At the mall the other day, every 20 year old I saw wore the SAME look: barrel jeans and chunky boots. It was a total turn off . I'm kind of glad I didn't invest in the super-chunky Chelsea boot look - I was pretty close to buying some earlier this fall.

Rachy - yes to more feminine shoes. A challenge for aging feet though. Points are tough. A soft bag and lush scarf are now on my radar too. Soft but not sloppy, if you know what I mean (like a puffy clutch over a slouchy shoulder bag).

thankfull2 - I LOVE Linda Wright too but don't quite think of feminine as a way to describe her style. She does have longer hair though, which allows her to wear mannish brogues and wide leg jeans without looking like , well, a man. I mention the Olsen twins only in relation to their brand, The Row. If I were extremely wealthy, thin and in my 30's , I'd likely swan around like they do in dragging pants and long sweaters - lol.

sun tiger - yes to keeping the drama. It's harder to do this for weekend/casual at-home clothes though.....which is where I want the change. Also yes to nicer , richer fabrics.

unfrumped - I don't think I'm being hard on myself - I'm simply looking for a bit of a change. I agree that shoes are a big part of a more feminine look. The challenge is now on. You also nailed it with more refined jewellery. I tend to go bolder to balance the short hair. Pulling out my smaller, better pieces today to start wearing them.

missvee - again, bang on with the footwear issue. My booties are all variations of the same - black, western-ish points or combat boots. I can't do a heel anymore, but there must be a rounded or squared toe suede boot that is chic and feminine. Not sure what to think of bags - not something I want to invest much in as I don't use them a lot anymore. But having one in a prettier colour is something Im interested in looking for.

judy - yes, it's a feel, but also a look. And great suggestions for a dressier blouse with jeans, layering etc.

shevia - having to wear a mask every where but at home has indeed taken away some of my identity - no lipstick and no earrings much of the time. Waist definition - I'll have to work up to that. Now that I think about it, my mannish sweatshirts and joggers or jeans show zero waist . Ugh.

gryffin - I'm not sure how to reply - because I think you've gone deeper than I ever did . I don't think I'm chasing pretty - but even if I am , it's because I want to? I can feel pretty when I'm dressed up , say , for an evening or special event . But around the house, in my weekend clothes, things I wear out shopping and errand running? That's where I'm looking to polish up the look to be less masculine and dark. Maybe that's not a priority to many people, but it is for me because my life is either at work in my uniform, or at home or running errands in my sweatshirts and jeans.

Suz - in the course of my workday , I'm surrounded by older, grey haired and grey-face (I know I keep saying that) women who ,while maybe dressed for a workout and not focused on their clothes and their look , all look the same - no discernible style, and almost sexless. No current haircuts, no style, no nothing. It's so depressing. But yeah, maybe it's the next phase of life, and I'm just figuring out how to negotiate it now.

Chiara - YES! So can you please box up and send me all of these wonderful pieces? You've described my goals to a t. Tell me more about your sueded silk joggers please - brands etc?

Janet - yes, I most definitely feel off in balance . Absolutely .

MaryBeth - really terrific insight, as usual. Yes to less sharpness and more to softer elegance. Also yes to needing an injection of the right colours. Earth tones can be very blah when worn together.

lyn67 - I agree with your comments about Linda Wright. And it sounds like you and I have the same hair. Yes, I'm attempting to let it grow for awhile although I don't have an end goal in mind . I'm also trying to get used to styling it less.

madeline - I'm very familiar with these women and love them all !

Wow CocoLion I love the vibe of that designer! It prompted me to go look at your recent WIWs and I am loving the edgy femininity of it all. Would love to see more, when you are up for it!

The targets:

jeans - something less mannish than a basic straight leg - maybe wear more flares or bootcuts ?

colour - thinking a warm bright pink - in a hat, scarf, mitts, bag, sweatshirt (sorry, but what the heck else do you wear on weekends that isn't a sweater??)

footwear - a refined, suede or leather boot - what I once would have classified as too traditional, haha. No points, no aggressive styling .

I'd love to add in a more feminine coloured puffer or casual coat, but this is the wrong time of year to be spending on myself. Can't buy everything

Lisa: I spent most of the pandemic holed up in our cabin wearing the same half dozen pairs of jeans on repeat, and growing in my grey hair. What saved me was having fun shoes and fun tops. I dragged out some old interesting embroidered loafers and all my old low heel booties, and brought up every washable top I could find in my home closet that had interest. I didn’t feel ugly except when I tried a boring pair of jeans with a mannish sweater, or with a plaid shirt. Those looks were too normcore for me. It sounds like you may have gone too normcore as well. If so, I would look for a few pieces (tops and sweaters) that are fun for you in a way that suits your modern interest: shape, color, material, fabrication, or pattern.

If it’s any consolation i don’t know if this is the right year to add a feminine puffer anyway. Many companies seem to be doing the sleeping bag style rather than fitted/flattering.

These replies have been so wonderful---so much food for thought. My ideas have already been proposed, so I'll just agree with the notion that you look fantastic---and still like "you" in tailored, close fitting tops. That alone adds to not only polish, but femininity in your overall loo. I also think you might benefit from a pop or even a PUNCH of color near your face--- or on your face! a bright lipstick, a very sumptuous bright large scarf, but tied in a loose "this old thing" way. Further, possibly having a less "done" hair style might create more of a statement for you. Last thing---what about a statement accessory, like a big silver cuff? I had never looked at THE ROW before. HOW ABSOLUTELY GORGEOUS are those clothes, especially the suits. They are neither my size nor my budget, but so lovely to look at.

I haven’t read the replies yet. I’ll go back and do that, but before I do, I just wanted to tell you I think these are totally understandable feelings. Part of why I keep my hair long even though it’s a pain in the *** is that I feel like my facial features are rather harsh and masculine. And though I have a curvy frame, if I don’t dress to accentuate it, it’s easy for it to turn into an amorphous blob.

Different issues, I know, but I guess what I’m trying to say is that even though I don’t think either of us is going to be misgendered by strangers on a regular basis, I understand the feeling. The Olsen twins really benefit from their iconically feminine facial features when they sport those minimalist Row pieces.

Has anyone mentioned makeup? I know you regularly play with and update your makeup, but maybe you could schedule a consultation specifically for tips that play up femininity and minimize sharp angles.

ETA: I remember my mom mentioning that as her skin aged, her go-to makeup brands started sitting differently and she had to switch things up.

I have only barely skimmed the replies as well, so apologies if this is repeated.

For me, I would go with more makeup, especially bright lipstick (which can be a problem if you need to mask for long periods of time). I'd also add more delicate jewelry (or even not-so-delicate). I find dangly earrings and layered chains necklaces particularly appealing.

I think you have warm undertones? If so, try tomato red lipstick with forest green eye makeup, rust lipstick with teal eyes, or copper lipstick with bronze eyes. Try to match up the makeup intensity to the colors you're wearing.

If you're cool, try mauve eyes with berry lips, navy eyes with scarlet lips (blue-leaning), or plum eyes with fuchsia lips.

Try subbing brown (if you're warm) or navy (if you're cool) for black.

(These combinations come from David Kibbe in his Facebook Four Season Freedom group. If you want to know more I'm happy to share. He matches three looks for each season with specific colors in the palette that go with the "intensity" of the face).

Lisa, something like this?
I’m not encouraging you but I think returns are free If I didn’t have already a black pair of flat boots, they would be mine.
also, the Bay might have a selection.

Also, would you like to add some casual dresses, like merino or sweatshirt dresses? Check Uniqlo, if you are interested.

This post has 1 photo. Photos uploaded by this member are only visible to other logged in members.

If you aren't a member, but would like to participate, please consider signing up. It only takes a minute and we'd love to have you.

FWIW, you always look polished and feminine, Lisa! Great make-up, nails, jewellery, and HAIR

Nodding along with very sensible Suz, Janet and Mary Beth!

As an aging person with very short hair, an un-curvy body, lots of fashion sneakers, absolutely no heels, and nothing form fitting - I understand what you are feeling! It has taken me time to navigate this new territory too.

I think you can add "the pretty" by softening the hard edge. Softer fabrics, lighter neutrals, more colour (needn't be bright), wider pants, patterns, earth tones, dresses, SKIRTS!!!!, tailoring, and refined footwear.

The patterned blouse from Anthro with the wide crops that you wore this Summer, was the prettiest outfit I have seen you wear!

I am very late to this thread, but I have loved reading the thoughtful replies to your interesting, introspective opening post. I appreciate how you are always examining things in such an open, direct way, Lisa!

It sounds like you have a path or direction in place now that sounds great! From my perspective, this time has been very destabilizing in general--paired with your retirement from your fashion-related job, your uniform at work, and re-thinking your hair, it's a lot to grapple with! As many have said very eloquently, it's always a balancing act (between practicality and style, minimalism and ornamentation, "too much going on" and boring, etc. etc.) and the balance shifts all the time as we evolve.

I have really enjoyed this thread.As you say Lisa it’s gone deep so l shall remain shallow!Prior to the pandemic ,when l used to wear acfual clothes ,l was starting to feel the need for a softer,prettierlook but my body type demands androgynous shapes and l am not good in traditionally feminine things like frills ,ruffles and the like so l partly understand your struggles.l felt that softer fabrics like tencel or silk in for example my best shirt shape alluded to my femininity as did Jewellery.Avoiding overly rate items,anything baggy and shapeless and making some attempts to switch up my hair helped.l don’t have great hair and really envy those who do.
I hear you on the older ladies who all end up looking the same but don’t you think that this won’t be you as you have an awareness and interest in maintaining a look?We are all different and some older ladies have different interests other than appearance whereas we on this channel are all very interested in maintaining a fashionable exterior!
l am sure that you will work it out as you have the interest and the ability to be stylish.

The part of what you say that really resonates for me is this business of having to dress for a very casual life, but at the same time wanting to look good. I guess the conflict between practical and aspirational style. And aging just adds to the difficulty because the young tend to look fresh in just about anything.

People who work outside the home in offices or sales jobs or even teaching (as I am doing now) have opportunities to wear structured and/or interesting clothing (even if they have to mask up to do it and thereby lose some of their facial features, these days). Comparing this year to last year, I can't emphasize enough the difference it makes to get out in the world and wear an actual outfit a few days a week! Even if it is quite casual (I often wear jeans to work) it is still an outfit, planned for the activity, and representative of my style and personality in some way.

Wearing a uniform, of course, is very very different! The advantage is that you don't have to think too hard about what to wear. The disadvantage is you can't dress as you'd like and feel constrained or even erased by the requirements.

Working from home all the time, I really did tend to wear my workout clothes a lot of the day. I was doing PT for my injury, doing chores in the house, going for a walk in the neighbourhood (where I see no one except a few people walking their dogs.) So I barely dressed and tended to feel invisible or generic, as you say.

It's just really hard to come up with WFH items that feel both uber-comfortable, practical, and truly stylish. You aren't imagining it!

Again , lots of thoughtful comments and replies . I’m so appreciative of all of it - even if I’m not about to start wearing bright lipstick - lol. ( major lip line wrinkles , plus all day masking makes it a moot point anyways ) .

Cocolion - how lucky you are to find a line like this ! Not in my colour or price range - but I see how it works so well for you .

Angie - yes to softer and more colour . I don’t see myself in skirts or dresses for my day to day life though , and wide pants I struggle with . There is little flattery factor there . But maybe I have to make these changes to get the feeling and look I’m after ?

Suz - yes , it’s all about living in a small city and living a now-casual lifestyle . Even a silk blouse makes no sense to me for wearing around the house or out shopping . The shoes are very much a part of this - and I know exactly what you mean about pointy looking slightly dated yet being what adds traditional femininity to a look.

Irina - these boots are interesting ! Maybe a little too elongated and edgy for my taste but worth trying . The Bay here has a useless mango dept : out of season stuff and no collections . No footwear at all . But the price is right ….off to take a closer look .

Skimming the comments and I don't have a ton I can add, but just commiserating on the smaller town/Uber casual fashion dilemma .. it really is HARD to feel stylish and pretty while dressing in a way practical to this lifestyle. And yes the 35 year olds look adorable on their workout clothes whereas I just look like I forgot to get dressed.

Echoing the colours suggestions, and I think it's a good time because there are lots of light and soft colours that are not pastels that are stylish right now ... I saw a women-of-a-certain-age the other day wearing a polished sweatshirt in a beautiful sage green and dammit I'd she didn't look quite gorgeous is it. Those colours -warm pink, soft green, light earth tones, would be perfect for your colouring and pretty-but-not-saccharine enough to suit your style.

Lisa, do you watch Succession?? Siobhan's palette!! Will find some pics ...

This post has 5 photos. Photos uploaded by this member are only visible to other logged in members.

If you aren't a member, but would like to participate, please consider signing up. It only takes a minute and we'd love to have you.

I've been meaning to respond to this all day but just haven't had a stretch where I could really compose my thoughts.

I still don't really have quite enough time to focus as I would like, but I do want to echo what Angie said about the Anthro blouse because I really was thinking the same thing.

The colours in that blouse were stunning on you, the shape was gorgeous, and your makeup was soft and perfectly balanced -- soft and fresh with just enough colour to make you glow.

Like others, I think you already present as very feminine, but I hope you find the tweaks that bring the added feeling of femininity you are seeking. I also truly hope you have fun with the process!

Lisa I am enjoying this thread immensely. Practical tips mixed with differing points of view makes a fabulous read. Nothing to add right now but thank you for starting this.

I am very late to this thread, but wanted to chime in with these items which are designed to add a little something extra to a simple jeans and sweater outfit without added the rigidity or formality of a shirt. I thought the decorative buttons may add the touch of femininity you are seeking.

I am in the hunt for more affordable options at present.

This post has 2 photos. Photos uploaded by this member are only visible to other logged in members.

If you aren't a member, but would like to participate, please consider signing up. It only takes a minute and we'd love to have you.

Wow, such a great discussion! I love it when things about style end up going way beyond style. Thank, Lisa! I can relate to the feeling that I'm losing the "pretty". Weight gain, no access to hair appointments (for reasons I posted about a few months ago in off topic), aging and stress...too many changes. Where did I go? Why don't I look like me? Etc.

That said, I've never really understood the concept of "feminine". At all. I'm serious, I don't get it. I'm female, therefore I am feminine. There are as many ways to be female as there are women alive. It drives me bonkers when feminine is taken to mean bows and ruffles (generally used as a put down), as if to be female is to be silly. Not that bows and ruffles are silly, but in those types of discussions the tone is derogatory.

I also can't stand books where the female character is admired because she's "not like other girls", with the tone universally implying she's better than them. A character we are supposed to like because her existence is a putdown of the whole female gender except for her? Who are these "other girls"? There is no universal standard of girls. I really hope this concept of only certain things are feminine will someday just go away.

I've failed (biologically speaking) at a basic female function because I couldn't have babies. I've had various feelings about that but at no time did I ever feel that made me unfeminine. I'm female, therefore I am feminine. Looking the way I want or used to is a whole different concept to me.

I never can explain my thoughts very well so I hope I haven't come across as lecturing or offensive. It's just a thing I've never understood and a word I've never liked. And it's probably miles away from what you intended for your post, but I've really enjoyed reading this discussion!

Peri - I always appreciate your thoughts. I understand all of what you've written here and nodded along while reading. But you're right, it wasn't the intent of my conversation - I'm not digging that deep. I'm simply looking to tweak my wardrobe a bit and am sincerely interested in adding something - anything really - that feels prettier and softer.

Roseandjoan - those are very interesting pieces - thank you! I'm not a layerer with shirts and tops in that way (bulk, wrinkling, fussing etc) but these are quite the perfect solution . I'll have to see what the North American options are! ah - back to agree with looking for a more budget-friendly option. It's not that they are unaffordable pieces, but I'm always so scared to order pricey items from an unknown label. (I know of them, just never seen in person). Such a great company though.

Helena - no, I don't watch Succession (tried, but couldn't find a single character to like) but her clothes are indeed pretty. Good suggestion ! All of this is giving me a major case of wanting to shop now- and it's the absolutely wrong time of the year for that!