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Advice on problem dresses

UmmLila (Lisa)

Veteran

It seems like every fall I swear that I will wear more dresses. I was really good about doing it this summer, but I only have bought one fall dress (a Betsy Johnson from NAS) because I have a few problem dresses causing me guilt.

The main issue I have with dresses generally is that I live in a cold climate and by the time the beginning of October rolls around, I'm not eager to have many exposed body parts.

Do you have solutions, or should they just go?

First dress: blue knit sheath with zipper trim. Problem: sleeveless. Solution: wear bomber jacket. New problem: navy blues never match. And what would be good hosiery?

Second dress: black knit sheath with woven autumnal insets. Problem: sleeveless. Solution: black Trouve jacket. New problem: dress inset is covered by jacket and it looks weird, secondary problem of hosiery.

Third dress: Not yet worn knit leopard and black. I thought it was going to be perfect when I bought it because of the sleeves and length. But because I have a wide waist I had to go up 2 sizes. So the bodice is wide and makes me look blocky. Also, the slit neckline just flaps open (I could sew it or install a snap.) Solution: alter the top. New problem: is it worth it? I have a not very good seamstress who blatantly failed at altering a Nanette Lepore that could have been flattering. I don't have other choices presently for alterations. (Country life problems.)

Fourth dress: old All Saints wool mix dress that has been a multi year problem. Problem: the asymmetrical hem is really short in back. Past my comfort level for length and not warm. Solution: leggings. new problem: looks like yoga wear?

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Dressing

17 replies

Latest reply was from shiny

Suz

(website)

Veteran

Oh, Ummlila, I am (selfishly) so glad you posted this. You must be inside my mind.

Once upon a time there was a woman named Suz who in her heart of hearts veered much closer to Team Dressy than Team Casual. She loved dresses. And wore them a lot. Or so she told herself.

Until she realized that she wasn't really wearing them.

Or, rather -- she was wearing them (and skirts) quite a lot. In summer.

She wasn't wearing them very often (if at all) in winter.

Light bulb moment.

1. Like you, I struggle with dresses when it is cold -- I'm not crazy about hose and tights and especially not the opaques I need to make them work in winter. It's not that I dislike that look on others -- but on someone as fair as I am, it tends to read "heavy" and "dark" and it means dressing in a lot of darks for cohesion, which ultimately brings my mood down. Like, really down.

2. I struggle to wear them to work at home. Except the super stretchy ones. I like to curl up with my kitty at home. Kitty has claws. Even if the dress could stand up to it, the tights can't. And even though in my heart I'm on Team Dressy, in my actual day to day existence on my work at home days, I'm firmly on Team Casual.

My solution? Such as it is... I vastly reduced the number of winter type dresses. I still have (and need) a few, but I do not have a huge selection.

For fall winter now, I own:

One Kamalikulture turtleneck sleeved body con jersey dress. Casual. I wear this for "at home" date nights with Mr. Suz or for more casual out of the house stuff. Works with a denim jacket, booties, etc. Packs easily.

One Kamalikulture sleeveless jersey sheath. This gets put away in true winter but works with a topper until late October for dressier events. This also packs well.

One sleeved David Meister sheath. A bit conservative. Works for more sober settings and/ or dressier events, and can also be casualized. Lined.

One Ralph Lauren knit sweater shift dress, sleeveless, that can be layered over tops like a jumper. And layered under stuff as well. Great travel dress.

I also have a special occasion Nicole Miller ruched sheath.

Your dresses are all beautiful. But I see the problem. The last one actually works well with leggings, I think, so you could wear it that way for work-at-home (or elsewhere). But the others...well...yeah. I love the first one, particularly.

Does the Trouvé jacket work with it, maybe? I wear navy and black all the time. And sheer black hose? Or casualize with a denim jacket if you are into that?

Sounds as if the leopard dress should go -- if it needs alterations that won't be successful, that's not a great idea.

I sympathize with your woes. Basically, for myself, I learned that what I might wear if I still worked in an outside-the-home job regularly (I used to teach) is pretty different from what I wear when I work at home. And winter complicates that even further.

viva

Veteran

I would try black hose (not opaque) with the first dress.
I would try the bomber with the second dress.
I would let the third dress go.
I would wear the fourth dress with the tights for very casual.

But then again, I am like Suz, not very successful at dresses. I have a few that I can work fairly well but only in specific ways. However, I still try, even though I know better. I just bought a $20 dress at F21 -- and on the way home from the mall, I pretty much realized I should have just thrown the $20 bill out the window of the car and saved myself the closet space.

Anonymous

There is no reason navy blues have to match perfectly - if there is enough of a difference, it can still work, no? But the navy dress with a black bomber would be really cute.

I must be off on my own dress island in winter, because that's when I actually wear them! I love opaque hose and a dress - my favourite is a printed navy silk dress with navy opaque hose and navy booties. I also love ponte shorter black dresses (60's silhouettes, not body con at all) with black hose and high boots. Is opaque hosiery out now and I don't know it? lol

Niki Lea

Veteran

I really like the combo of the bomber and dress in #2 and I agree with Lisa that the navy blues probably don't have to match. It's my favourite combo of the bunch. I'm wearing navy and black together today.

All of the dresses could be worn with tall boots and tights for extended winter wear, but I'm not sure what your specific climate is like. You could also try a scarf that pulls from the colours in pic #3, maybe also tall boots and a relaxed boyfriend cardi?

Laura (rhubarbgirl)

(website)

Veteran

I don't wear sleeveless dresses in cold weather either, even if I theoretically have toppers for them. They're just not comfortable for me. The winter dresses I do wear, for regular days as opposed to special occasions, are sweater knit. But like Suz I don't have I be work presentable every day.

What about trying some things over leggings and boots? I find leggings less constraining than tights for some reason.

ironkurtin

Veteran

Do the Donna Karan and get opaque black tights! Many many people (like Jcrew) make tissue-y LS tees that look great under dresses. Then throw a cardigan over, add a scarf, and go!

LadyLilac

What a wonderful post! I love thinking of ways to recombine classic pieces across changing seasons.

My tastes may differ from yours when it comes to winter dresses, but FWIW, here are my two cents below.

I practically lived in my navy sheath dress and black sheath dress last winter, as I had a lot of fun experimenting with different combinations. I really liked layering turtleneck sweaters (more of a tailored fit) under the dresses, mainly red, cream, and gray, which I think would work with most of your dresses. Many times I added a necklace or scarf, or a belt around the waist for added color and/or interest.

As a slightly less bulky option, I also layered long sleeve tees under the dresses, such as these BR Angie picks from last December. http://youlookfab.com/2013/12/.....an-outfit/

Tailored button-down shirts also work well under sheath dresses, but I had to take care not to look too much like an airline hostess ( i.e. navy sheath dress over light blue button-down shirt)

Finally, I enjoyed layering bulky sweaters over the tops of the dresses, which essentially makes them function as pencil skirts, but I liked the seamless quality and not having to worry about two separate pieces/tucking, etc.

I wore flats and tall boots with all of the above combinations, but I think I liked tall boots the best.

Concerning hosiery, I either wore fleece-lined hose for warmth or used Angie's idea of layering two pairs of hose. I was surprised how warm both of these options were, and I am like Angie in how easily I can be cold. Black is not my favorite neutral, so I tended to wear varying shades of grey, navy, or chocolate brown, so if you're worried about too much depressing black/darkness as Suz mentioned, these could be other options. I really liked the Hue and Via Spiga brands. Patterned tights could work with your black dresses for more interest.

I hope this is helpful!

K. Period.

Veteran

Hmmm. So, I think hosiery and footwear solutions will turn out to be the solution to each of these problems. First, how dressy do you need these to be? Second, how comfortable are you with color?

With the first one, the non-matching topper doesn't bother me. I would use the opportunity to create a strong color-blocking tonal feel by adding a very deep purple tight.

I would do the same for the second one, but with a fall-toned (chocolate? dark dark mustard?) and consider wearing tall boots. I also often wear a pair of heavily textured open weave tights over a pair of colored tights to knock back the color.

The third? I would also let it go.

The fourth? I think it looks great and not yoga gear at all with the leggings, but I would add a pair of sexy booties to go with it.

Hopefully one/some of these will be helpful!

Suz

(website)

Veteran

Lisa, dark (esp. black) opaque tights are not "out" by any means. But as Angie warns, they have to be worn intentionally to look good. And an awful lot of people in our country just throw them on for warmth without thinking about the outfit.

I actually think they look stunning on a dark haired person -- great bookending.

I find them harder to wear myself. I feel unbalanced if I don't have a fair amount of dark elsewhere in the outfit. And too much dark depresses me. I seem unable to find the multitude of colours that others mention -- where I live it is basically black, grey (if lucky), navy (if lucky). And then my cat puts runs in them anyway. So...

Anonymous

I wear basically two kinds of dresses...sleeveless for 3 seasons depending on toppers, and sweater dresses for cold weather, usually with woven leggings and boots. Try black jackets with the navy. Maybe skinnies (woven, not knit) under the last dress would help you feel that it looks like yoga gear.
The second dress with inset looks ok to me with that jacket worn open. In inset will show especially as you move. I'd pass the third dress on unless you really want to wear it. Then it may be worth taking it to a tailor and ask what it would cost to get it to fit you.

UmmLila (Lisa)

Veteran

Thank you all for your insights. I already knew I needed some dressy knee boots. I appreciate the creative hose ideas. I think I'll try to work with the blue dress on that.

Basically, though, I'm probably never going to be a huge dress wearer in the winter. As Suz says, it's a disappointment when you really prefer the dressy look.

The other part of the dressy look that is tricky for winter is that if you prefer to wear a blazer, it doesn't always fit under a coat as easily as a sweater will. I do have my print blouse, cardigan, jeans formula, but I'd like to not do it every day. Perhaps I can work harder on finding dressy wool trousers to change things up. Speaking of that, I have some problem child dark red wool tweed trousers that I already need help with and will probably post on soon

unfrumped

Veteran

Great advice already. I think you either have to find your "formula", or let it go.
I have to wear tights for warmth, and I mean opaque or fleece, so none of the bare leg or nude hose looks will work for me in cool fall or winter. So I have to find the footwear-tights combinations that work for me and then ask what is the skirt or dress that works with that! I really like having a choice of that silhouette so I made an effort to create some outfits especially for not-freezing days.Footwear is always a challenge for me because a perfectly fitted bootie or shootie, that is comfortable and stable for being on my feet a lot but still looks refined with skirts or dresses, has been a HEWI

Suz makes an interesting point that dark tights look doesn't match her coloring and mood as she would like. I do pretty well with that because I have dark hair and sort of "winter" coloring. I think you could get away with black tights even though you're blonde, but might also like gray, or the tall boots idea.

Suz

(website)

Veteran

I do have my print blouse, cardigan, jeans formula, but I'd like to not do it every day. Perhaps I can work harder on finding dressy wool trousers to change things up.

We understand each other. For me, last year, it was an endless cycle of jeans (different cuts, colours, and patterns, but, let's face it -- still jeans), fluid fit pullovers, and (sometimes) scarves. I love the look, I love the ease...but boy oh boy was I ever SICK of it by the end of 3 months!!!!! (Especially the skinnies tucked-into-tall-boots version that I pretty much need to wear from January to March.)

My mission this autumn/ winter is to find a few ways to switch things up. Dresses and skirts, as you've discovered, can be problematic. They'd be no trouble at all if I worked in an office. I do have knee high boots (finally, after a difficult 3 year search). And I do have some toppers that work with them. And my coat actually fits easily over the toppers. But...the fact is, I rarely wear them at home, for the other reasons mentioned, above. I do wear them when I go out in the world (occasional meetings and occasions). But not on work-at-home days.

So...this year I got my first pair of leggings and a couple of tunic length sweaters. This will be one new silhouette for me for at home days.

I also got a few cardigans so I start to wear my shirts (as you are already doing....thanks for the inspiration!!)

And I own a few pairs of non-jean trousers that I also use.

Apart from that, I honestly don't know what to do.

This is one reason I have started to love summer. I can wear so many different styles and silhouettes, so much more easily.

Angie

(website)

Fashion Stylist

Dresses are a Summer thing for me - and these days always sleeved. I wear sleeved dresses in Summer that I see bloggers wear in arctic temperatures. There is no way I could do that. I run far too cold.

Furthermore. I don't like to layer over dresses. More often than not, it ruins the look to my eye (although denim and moto jacket are the exception). I don't really like to add hose either. I like to wear a dress as is - add shoes and bag - and be done. So there you go. Dresses (and most skirts) = Warm to Hot Weather dressing.

I think #5 would look great over skinnies with a long coat. I quite like the way the collar flaps open.

Try tall cognac boots with #8 to break up the all knit "yoga wear" look.

Janet

(website)

Veteran

You've already gotten great advice, but I've been reading your issues and everyone's responses with interest. I have a problem with unworn cooler-weather skirts and dresses because my life is really casual and it's just easier to reach for jeans every day. Plus the footwear/topper dilemmas... I have come to realize, like Angie, that dresses are mostly a warm-weather thing for me. And even then, I didn't default to my dresses this summer the way I have in the past because I discovered some other silhouettes that helped me change things up. Consequently, I was much happier with my summer style this year than ever before.

It will be interesting to see what happens this fall/winter with my existing dresses. I culled some from my closet last year, and I have a feeling more might be going when I do my seasonal closet switch in October. My F/W dresses are all sleeved, but still require more effort to style, it seems, than summer dresses, which I can just throw on, add footwear and accessories, and go!

I love Angie's idea of tall cognac boots with that last dress. I've been thinking of adding cognac boots to my collection. Such a nice rich color!

Jules

Veteran

For the last dress I think you need more texture contrast. The booties look like suede, how about tall leather boots instead? And then maybe a woolly and/or coloured tight. I think the yoga (ninja?) gear problem is coming from everything having the same black colour and soft texture. It's supposed to be fashionable to mix black, brown, grey and ink this year (Angie did a post) so if you have other coloured footwear options give those a try. Do you have a leather moto?

shiny

Veteran

I wear dresses all four seasons. Right now, with it just beginning to feel like Fall, I'm wearing them sans hose but with booties that can accommodate socks. If my feet are warm, I am warm. For topper, I am donning a jean jacket (white or denim) or cropped moto. A colorful pashmina also adds warmth too.

When it gets a little colder I'll layer a slip underneath, and pop on a cardigan (either a long one or a shorter one, worn open). I'll wear tall boots with thicker socks. I can get away with bare knees for a little while. When I can no longer do so, then I usually go with micro-fishnets in nude (with wine or brown boots) or black (with any of my boots). A little colder ? Then sometimes I'll layer two pairs of hose -- I like the look of a colored hose (blue, purple) under black micro fishnets. It's a subtle look. I also do patterned hose sometimes, as the pattern adds interest.

When it's really cold, then I switch over to sweater dresses worn with opaque tights, sometimes fleece lined. Most of my favorite sweater dresses are not solid black because of the head-to-toe black. I do have black sweater dresses and when I wear those, I go with patterned tights, or layer colored tights + micro fishnets, just to liven it up a bit. Or tights that match my wine boots. A topper and/or scarf and/or handbag and/or coat is where I then add color to break up the all-black palette.

I'll also say that it's difficult in the transitional season to adjust my eye to opaque tights. It gets much easier as we move into winter, because that basically is the "uniform" around here, for practical reasons.

I really love dress #4!!! I'd wear that in a heartbeat. I'd pair it with tall boots and if I did opaque black tights + black tall boots then I'd add a colorful scarf to break it up. Then again, that would cover up the asymmetrical neckline. For right now, I'd go sans hose and pair with my leopard booties with socks. You'd be surprised how the addition of socks can make the rest of you feel warmer.

Then again, I run hot, not cold!