I’m no use here Lisa, I have no clue how a sales rep. should dress. It’s been 9 years since I have talked with a Pharmaceutical Sales rep. They came to my office all the time trying to get my attention. Most of them were good looking young men! LOL! I’m sure the marketing experts sent the good looking young female reps to the male physicians offices right! How awful! In any case, what I remember about the few female reps that did come to my office was they each had a unique way of dressing. One wore beautiful, trendy dresses. One had been a news reporter in a previous career life so she looked like it with her pant suits and blazers, always conservative, but impeccable. Another was more avante garde, and had a unique arty look. No one showed up in polyester pants and printed tops though. That description made me laugh.

My point, if there is one, because this is mostly pointless, is that I really didn’t think about what these people were wearing as much as how annoying they were vs. how nice they were. I really ignored the most annoying reps, and am still friends with the others even though I no longer have a private office and do not see any sales reps. So, it’s just the initial impression you need to make, your personality carries the rest, and you are funny, and warm, and nice here on the forum, so I assume you are in person too. If you can find something like a skirt that makes your outside feel better, than everything should line up well! Good luck!

lisa --echoing what has already been said...you have incredible style, and always, IMO, look put together....so i'm sure what ever you decide to do, you will look fab....that being said, i have a personal thing about pencil skirts, for me, they are a "i just graduationed and this is my 1st job and i need to dress like a professional" thing, because every year we hire 30+ new grads for our training program and almost everyone of the young women wear a pencil skirt on the 1 day....its like a tell.....but, i've been here long enough to know that if Angie is recommending them, they are what you need!

Lisa, re your angst at buying skirts. Tailored items that fit are the perfect way to look professional. I expect to alter my tailored work wear. I include in the cost of purchase the potential cost of alteration. In relation to pencil skirts, I find just a subtle tweak of pinning in the hem to a less wide hemline really change the look of the skirt and make something that looked dreadful to being much more streamlined and slimming.

Hope your shopping expedition is a great success, it is a shame that you don't live in the same city as Angie.

Lisa - so sorry. You've been having such a tough time. It's awful when you don't feel so good about your clothes you can forget about them. I echo everyone comments. A pencil skirt with a top over it will minimize midsection and ramp up formal. Concentrate on blazers, shoes, accessories. Lisa do they have JJill in Canada? It's a lot of knits. A lesser price EF wannabe. However if you could find ankle pants and skirts in neutral fabrics they would be Forgettable but work at a lower price point. There are some good layering tips. Get your blazers out. Begin outfit creation. Find the missing pieces. Then stop looking for THE pants and skirts. Find what can work now. Once the outfit works and you have a working elevated professional wardrobe see what needs upgrading. I would look for stretch and knots. Much easier to fit. Hugs to you.
ETA: also look at simple shift dresses. JJill, EF sale they will glide. Layering tops and sweaters. You can layer a cropped sweater or tunic over a dress and it's a skirt outfit.

Lisa- it doesn’t have to be a big jump. You moved toward casual slowly, now move in the other direction the same way. It won’t feel jarring to you or people who work with you. People on this site always talk about wanting to be themselves- so my attitude is be yourself but “dabble “ in different. It’s less expensive and gradual is good and you are more likely to be happy and more successful with results ( think of it along the same lines as dieting- lol)
I am not a skirt person either but a nice dress pant with any of your current jackets or blazers can give a real polished look.
Never underestimate the power of a colorful statement necklace or scarf and footwear. Even if you are not comfortable with scarves just having it under the jacket collar and ends hanging loose makes people think you are dressed to the “nines” to borrow the term.
Necklace with a tee and blazer will speak professional also.
Jeans with a blazer, scarf and low heel can be a great job look.
Lose the trainers and casual sandals for a mule, slide, less casual sandal , snappy boot, or even heels.
If you are afraid of skirts- follow Katerina - she does polished pant look better than anyone in my opinion.

I was liking the idea of a dark plaid pencil skirt with a pastel sweater the other day, but you know how it goes to have an ideal look of something in your head and not find it.

I do like Angie's idea of the pencil skirts for you, especially as you are very selective about your trousers.

With regard to pencil skirts, it's still cold. What leg wear would suit?

Lisa, my pencil skirts sit at my natural waist, which is quite high anyway. If I wear the same size as I do pants, they tend to follow the lines of my body without constricting me too much. I can’t tolerate much constricting, so that’s key. That said, I used to have more pencil skirts in a bunch of fun patterns until they mostly got too small. I now have 3-4, but am willing to add 1-2 more. Once I’m shopping again, I may try Ann Taylor’s curvy fit.

Re: how to choose a size for pencil skirts. My body has also changed a lot since I was younger, but when I did have a larger hip to waist ratio and tried to wear pencil skirts on my hips, they rotated around my waist so they were back to front and thus required frequent adjustment in annoying fashion. And the point is to feel professional and put together, right? A higher waist will also be girdling as Angie mentioned. I'm also short waisted and agree with all of Angie's suggestions, actually.
However I also have a slightly different idea although it is vague. It sounds like you can wear what you want, basically, and you don't see the same people every day. So instead of going in a "business" direction with skirts, trousers, etc, have you considered just amping up your already edgy style with a few really great pieces that you love? I'm thinking trendy, edgy but good quality, shoes and toppers over some kind of simple uniform (could be great jeans and a simple layering shirt). Nice leather moto, Smythe blazer, stuff like that you love and makes you feel great.
If you are not seeing the same people all the time you would only really need 1-2 great outfits per season (of course you would build more over time). I work from home and I've basically gotten it down to one great "going out" outfit for every 6-8 week "season" (although winter has been very long this year!). Since you enjoy some trends, and seem to frequently tire of things or change your mind (apologies if I have this impression wrong), this might be something that works for you too, at least until you build your wardrobe over time.

Bella, it sounds like I need those pants too! Pants are so hard for me. I passed along my last pair of wide-leg black trousers (which were probably near 15 years old) when I wore them for a funeral and realized they were getting faded. Every once in a while, it would be good to have a nice flattering pair of black trousers that I can dress up or down, but I haven't found that yet (although I have not been actively looking, just generally keeping an eye out). Everything seems cut so narrow through the thighs, or has an annoyingly high waist, which I just cannot wear -- I just end up with unintentional drop-crotch.

It's a good thing my life is so casual and I can wear jeans every day if I want!

Janet - yes, definitely check out your B&M MANGO. I had a pair of pants from MANGO in a similar fabric years ago, and wore them for a long time, too. They really make me feel good about the whole dreaded pants thing.

Lisa, you’re selling yourself short again. Your style is fab. You already have great hair, makeup, jackets, shoes, and accessories. All you need are some trousers or a couple skirts.

Why not scroll through Angie's ensembles posts for inspo? Below are a few of my favourites that I could see providing a jumping off point for you. FWIW, I think most folks will look at your face and your feet. You've already got great hair and make-up, and enough shoe love/mojo that I think you don't need any help there. Then there is the whole great scarf/outerwear issue -since you are usually coming in from being outside.

An easy peasy outfit fave for me when I'm feeling less than fab about pot belly or muffin top is a dress with gentle shiring at the waist topped with a jacket of some sort.

I haven't read all the wonderful responses yet so apologies if already covered. It sounds to me that bottoms are the concern. You have lots of denim but trying to change that up. What about having a simple ankle pant made to measure. It would be a perfect fit - perhaps black. If it works well you could get a second pair.

You've got toppers, accessories, makeup, hair, and probably footwear covered. Possibly tops as well (and anyway, they are usually easier to find/ add.) So it's just bottoms.

Pencil skirts are a great idea!

A person does not have to be model-thin or tall to wear a pencil skirt. Two forum members who rock a pencil skirt with the best of them are Beth Anne and Transcona Shannon. (There are many more, too, obviously. These two just come to my mind because it was part of their signature look, though Beth Anne has had to adjust for new job realities.)

Anyway, point is, pencil skirts work on many different body types -- they're hardest for a full-on pear shape but work for pretty much everyone else. Also, they come in different levels of formality (with those VC tube skirts being the most informal and body con, and a woven lined pencil skirt being more structured). You might find a ponte skirt would be a great compromise. More structured and "safe" feeling than a flimsy tube, but still a bit of give.

Another option -- a little more casual -- a denim pencil skirt.

Why a pencil might work for you: you like long over lean (this works with a pencil) or structured over lean (ditto). You don't like to tuck. This silhouette is basically like wearing a pair of slim cropped pants except it shows off your legs a bit (and is cooler in summer -- a bonus.)

Bella, it’s too bad the nearest B&H Mango is in NYC! I’ll be there in a month for a bike ride, but will probably be short on time. Maybe I’ll get a brief window of time to check them out.

You guys! Thank you for all of your great ideas and thoughts. It all sounds so easy.......

annabelle - I've done a thorough closet edit and am covered on the bag/scarf/accessory front. I like your idea of figuring out how to dress up my collection of bomber jackets - and yes to a mid-heel chunky loafer or oxford. Good ideas. Laughing at the "full on BR like a mom going back to work after a decade" . EXACTLY - NOT what I want to look like, and it's so true of BR.

gradfashionista - thanks for the tip on the Theory pants - I'll go check it out asap.

Jane - not familiar with Wolford other than their hosiery. I'll look them up - thanks! I do have a pair of culottes waiting for warmer weather - good suggestion for easy-fit. I find CM too trendy and not for my body anymore. Everything in their is designed for the size 0's and 2's of the world. I used to be one of their biggest customers - literally - but my last couple of trips in have left me shaking my head.Teeny tiny, cropped, fluffed, frilled and cut-out clothing.

rachylou - not weird at all. I'm not necessarily on my feet all day, so I can get away with a range of different footwear. I do have to look for something to wear right now - like a kitten heel or a flatform oxford. You're right.

tulle - thank you . And I agree with the pencil skirt idea and how smoothing it can be....but yeah, the leg wear issue is very real. Nude fishnets? Does anyone still wear those?

bella - ack - I only wish there was a B&M Mango near me. I've only seen one, and that was in Montreal. However......I'll go on their website and look around. I haven't thought about that brand in years.

Style Fan - glad you agree - and thanks

Chris987- oh, I can deal with sizing, I'm pretty much over that stumbling block now. It is what it is. I just want it to fit and look good, regardless of the size. Off to look at pencil skirts today !

Ledonna - thank you . I am nothing if not honest and open. Hiding one's feelings and experiences make no sense to me. I get my best ideas when I come right out and lay out the questions and issues

ChrisM - I've never tried JJill - I've seen it , but there aren't stores here in Canada. But I'll check them out on line asap - thanks for the recommendation !

Staysfit - you're making me laugh this morning , thank you I am better in person than here on the forum - hopefully a little warmer . Writing gives the wrong impression sometimes . But thank you for the compliment . Those characteristics are pretty necessary in sales.

kkards - see , I have always seen pencil skirts as "first job" too. Glad I'm not the only one. Either first job, or incredibly chic and successful managing partner in a tv law firm. However ......there is no doubt this isn't my first rodeo , so perhaps the style will have come full circle for me now !

Bijou - you are so smart. And I really wish I lived near Angie too. I'd hire her in a hot minute.

gryffin - ugh. I must sound very pathetic. Which, yes,I feel at times, but I need to stop it ! No JJills in Canada but yours is the second recommendation for it. I need to copy your look - it would work perfectly for me. Dresses are my saviour in summer, and I can't wait to start wearing them. It's too cold for bare legs just yet, but as soon as it's warm - I have a few that ramp up my look. But back to the separates - yes to knits and some layers. Off to check out JJill.

efbgen - thanks for your thoughts! You're right about scarves and jewellery - and I love to wear both:)

ummlila - oh I get that. Happens to me all the time. I get an idea, and cannot execute it at all. You'd look great in a dark skirt and pastel sweater (lilac, maybe ?!) And yes, the big question is hosiery. Far too cold at the moment for bare legs, and black hosiery seems too dreary. Not sure. What do you wear on your legs at this time of year??

Jules - your ideas are what I'm aiming for. Not to go all lawyer-y suits, but to use the components I do have to get a more polished look. And yes, I don't need a ton of clothes because I don't see the same people every day at all. Laughing at "frequently changing your mind " - who me? Haha - you are so right.

JAileen - yes, I do come cheaply these days Off to find pants and skirts today .

Carla - great idea to go through some ensembles . I have a bunch saved on Pinterest - thanks for suggesting it!

Glory - thanks for chiming in . Yes - pants and skirts seem to be the place to start.

Suz - hmm. All good ideas here. My hesitation , well, never mind . It's just there - skirts are so exposing . But you're right , I can still do a long top or a more fluid top at least... I am not a fan of denim skirts (regardless of what size I am) and don't see myself wearing one. They have never been my thing. I think you're right about ponte being the best bet - I got rid of my old VC tubes a few summers ago. It's funny : I had a lovely EF knit crepe pencil skirt that I bought on deep sale a few years ago. It was too big and I had to take it in significantly to get the fit I wanted. And then NEVER wore it. Don't know why. Just felt too uninteresting. Now I'd kill to wear it. Wonder if I still have it.....

For those who find pencil skirts hard to fit - Lisa p, you too - you need the stretchy tubular styles that are fitted and tapered at the hems. They fit EVERY body type - like leggings. Very forgiving and comfortable. Sooo much easier then pants. Find a substantial one WITH LENGTH. Try to get good fabric. The art comes in how you're going to STYLE them. That's where you can be very clever. I'm here to help. Use me.

I can’t really add to the above advice but I just wanted to say that you always look very nice and put together when you post on the forum,l understand feeling blah but your outward appearance doesn’t seem to reflect your inner turmoil if that’s any consolation.

Lisa, just a brief answer, traveling today, will be back tomorrow. I wear a lot of professional clothes. Agree with Angie and others, pencil skirts are easier to wear than you might think. It is the only skirts I wear - I am also self conscious about my figure and use some tricks - like looser tops not tucked in, ruffles that are placed vertically in the middle of tops and blouses, long scarves, drapings etc. - all these make a nice vertical line and work perfectly with pencil skirts. And blazers of course - right length is the key. And I don’t use polyester printed tops Hope you find some outfit joy soon!

It took a lot of tries before I found the ponte pencil skirt I’m wearing today so don’t get discouraged. Also, I have found I have a magic length; any longer and it becomes difficult to style.

My go to work looks are black cropped pants or a knee length dress. I am an easy fit in a dress and less so in the trousers.....

I see no reason why you won't rock a pencil skirt - I think the two keys are quality fabric and length (below the knee). Aside from that it is the styling and you have had lots of good ideas.

I think a great pair of black or charcoal or navy trousers/work pants would be a great investment for you. Tailored perfectly. I don't know where I would start in Canada but here I would look at Sportscraft, Karen Walker or even getting some made for me. Such a good base, always sharp, and suitable all year.

I also think a leather or faux leather skirt would be great for your style,
and a real workhorse. It may take some time to find the correct fit though. But if you could it’d be fab with your look. Imho.

Hi Lisa- I can definitively relate to the struggle that a changing body can create on one's style mojo.

Like others have recommended personally I would focus on finding 2 or 3 well fitting neutral pants and/or a skirt plus some good quality neutral layering tops to use as a base for your wonderful toppers and accessories. Ponte would be prefect for a pencil skirt. When I am at a heavier weight I have to watch that the skirt length is long enough that the skirt does not look wider than it is long. Length proportions seem to be more critical.

I would also focus on creating some more polished looks utilizing dark wash jeans with more dressy accessories, shoes and tops. Susan at https://unefemme.net does this really well. At least I think so.

Hope this helps.

Far be it from me to attempt to give your stylish self any sort of fashion advice. I just looked back to see if I had missed any of your recent postings, and I am just in AWE of the outfit you put together with the green tunic from the company you rep. As someone here already mentioned, presumably you see different people most days, so a core of 3 or 4 “client visit” outfits could get you by for a while? You probably have the makings of that already, and can build from there.
Just know you have a lot of company in the confusion around these late midlife body changes. I mean, what relationship is more intimate than the one we have with our own bodies? How dare they go changing on us, right?!? One does learn the tricks for coping, though, and I promise it gets easier to find proper fit and proportions. And you already have the skill set and accessories to make a few basics look spectacular!
My saving graces during the most confused stage of transition were a single pair of dark wash straight leg denim jeans with a fair amount of stretch and a pair of those Eileen Fisher slim leg washable crepe pants hemmed to ankle-baring length. Yours will probably be something more fashionable and fab- like a pencil skirt! - but once you find it, everything else will start to fall into place.
Can’t wait to see what you come up with!

While I take Kkards point about pencil skirts being a classic graduate/first job look, I think the variety of pencil skirts available these days will give you plenty of opportunity to find one that is interesting and suits your style: asymmetric hems, buttons, side or front zippers, front or side slits, ruching, prints (plaid, floral, abstract, you name it). I have a black windowpane pencil skirt which has a black side zip that I think you would love (I think of you as being a fan of plaid type patterns?) and I think it would suit you very well.
I respectfully disagree with the suggestions that the skirt needs to come below the knee. I think that midi length is trendier and very elegant but harder to style with a longer top worn untucked, even if the skirt is tapered (but tapering is good!).
My approach for pencil skirts is (for what it's worth): the longer the skirt, the shorter the top; the shorter the skirt, the longer the top. So that you end up with a 2/3 to 1/3 proportion in each case.
I think your wrap gingham top could work well with a longer, midi length pencil skirt because it is shorter and creates waist definition. For longer, more tunic style tops (the type you would wear with skinnies), I think a shorter skirt can look really good. And by "shorter", I mean just on or above the knee, not a mini. (Not that there's anything wrong with that.)
Just my 2 cents of course.

Agree with all the previous posts. Pencil skirts are surprisingly forgiving. I bought two from Gap (one navy and one black).
Perfect length to just below knee and machine washable, no ironing.
I also discovered BR has beautiful print blouses. I bought the Dillon style and it fits very well. Price point is affordable with their sales which seem to be every other week! Good luck and have fun with it. Try driving shoes for flats! More supportive than ballet flats!

Heh, Lisa, I just banished three beautiful but unworn, too-small, and too dressy for my life pencil skirts from my wardrobe — if you’re a size 8ish I’ll send them to you! One is black and stretchy, with leather panels on the sides.

Thank you all, for your ongoing thoughts here. I truly appreciate them all. I spent about an hour in the mall yesterday looking for a softer ponte or jersey skirt, and do you know I found only one worthy of even trying on. I could not believe the lack of skirts in stores. Hudson Bay: in any department had blazers, work tops, and pants. No skirts in any of the collections except for the odd very tailored pencil with a waistband. It went from that extreme to Anthro maximal print options . This may well end up an on-line exercise.

I have a magical knit animal print pencil skirt that I bought on whim. I had no reason to buy it other than I love animal print and it fit perfectly. It does have some structure and a zipper but if needed I could do yoga in it. Also, it accommodates weight fluctuations. I reach for it in three seasons, it's not a summer skirt, and I've worn it with many different toppers and boots/shoes. All this to say that it's by Calvin Klein so perhaps you might want to do an online search for that brand. And I'm old school so I do wear panty hose or tights with my skirts unless the temperature is warm enough for me to go bare legged.

Can you order online?