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Thrashing Out Dressy Look Challenges

Angie

(website)

Fashion Stylist

On always trying's thread, many mentioned that dressing up for events, settings, and formal occasions is the worst and the hardest, and an ongoing challenge. Here is the thread and the responses:

https://youlookfab.com/welookf.....-dress-for

I've started this thread so that we can discuss the challenges and find solutions from them.

What are the challenges?

Dressing

75 replies

Latest reply was from Stagiaire Fash

JuniperGreen

Veteran

Dressy events that I WORK during are an ongoing challenge for me. I have to look pulled together and polished, but working an event means lots of hustling around, lots of walking or at least standing, bending down, picking up stuff, and carrying awkward items.

So comfortable footwear is a must, nothing too tight or too warm, and pockets are really helpful since I need my phone on me but carrying a bag isn’t usually an option.

I’d love to find more long gilets with functional pockets (blazers are often hard to move freely in)... layering them over blouses and trousers worn with dressy loafers is good, but the only one I have is starting to show signs of wear.

kellygirl

Veteran

So many challenges but mostly because they are out of my comfort zone. I'm confident in my normal attire but thrown in something that's more dressy and I start second guessing myself. I like to blend in and I don't want to be overdressed or wear something too young/too matronly nor do I want to be be cold. And then I have to figure out a hand bag. It makes me want to stay home!

LaPed

Veteran

Staying warm is the biggest challenge, along with other footwear considerations. I need sleeves or something that looks good with a topper. Toppers are hard because blazers can look too office-y, wraps are fussy and not warm enough, knits usually feel too casual.

Prefer trousers or a dress/skirt that looks good with high-denier tights, because I'm miserable if I wear sheer hose in the winter.

Pumps and loafers don't stay on my heels, so I mostly look for ankle straps or oxfords (but ankle straps that hit in the wrong spot chafe and cause blisters). Pointy toes and even many almond toes are too narrow in front, yet I often swim in a wide size if it's a style where I can't add a thick sock. Shoes need at least some rubber tread, because walkways are icy and foyers are often wet and slushy too. No smooth or leather soles unless it's a style I can have a cobbler add rubber to.

And then to top it all off, you need the right length/volume coat to... top it all off!

Summer is easier; I can get away with daintier shoes when I can go barefoot, bare-legged, and I find plenty of summer dresses and skirts that I like the look of. Breezy silks and linens. I also feel like summer looks are more appropriate with less/daintier jewelry, whereas winter outfits with thicker fabrics often look better with more bling and chunkier jewelry, which I don't have.

cherylm

Dressy events when the weather is dark cold wet and rainy. Dressy shoes tend to be delicate so the transition from the car to event is always an issue as is outerwear. Also - dressy clothes tend to be bare and of silky not warm enough fabric. So easy for men, they just wear a suit and they are done .

kkards

Veteran

fortunately we no longer have a company black tie event....that was always a balancing act of finding the right mix of festive and corporate...
now its more a challenge of understanding when someone invites you to their home for a holiday party, what level of festiveness is expected...

Staysfit

Veteran

I haven’t gone back to read the original thread yet, but the biggest challenge I have is finding appropriate toppers for my outfits. Most of my dressy items are sleeveless. I have been hunting for some good metallic options because I think they go well with most everything. I found a silver blazer, but it is too tailored for some of my looks, so I would like to find a shawl or cape like option as well.

nemosmom

Veteran

Accessorizing a dressy outfit is my biggest struggle. Does the neckline of my dress or top work with a statement necklace or should I go for a more delicate piece? How big or long of an earring? And clutches — what color or detail should I look for? Should it match my shoe? Coat? Skirt? Hair? Should it be beaded? Do I look pulled together and sparkly or like a disco ball?

I give up on clutches and usually carry my phone, but that doesn’t work for nicer events, and I have to be accessible should the sitter need to reach me.

Anonymous

My first challenge is that I NEVER feel authentic. That translates into feelings of insecurity and discomfort.

ChrisM

Veteran

++ what Sterling said.

Add to that costs for items that get worn only once every so often, fluctuating sizes between the occasional wears and I am over it.

Insecurity r us.

Angie

(website)

Fashion Stylist

Thanks, ladies. I HEAR YOUR CONCERNS. They are real, warranted, and we can find solutions for all of them.

La Ped, Cheryl & Staysfit, there are ways to feel warm in dressy attire - a MUST for me too. You have to say no to skimpy dresses, wear hosiery, layer, insulate, wear party separates and warmer dresses, and wear a topper or two. You can also swap out your shoes at the venue.

La Ped, I have a lot of empathy for the shoe situation. You can wear sturdy fun boots and make the outfit look fab I'm sure. I'm happy to help with my 2 cents when you need specific outfit help.

Juniper Green, you have a VERY unique situation, and I'd love to thrash that out with you in great detail. YES TO COMFY SHOES.

Sterling, try creating a party outfit that begins with drawing from your signature style so that there's a common and comforting thread running through the two sets of dress codes.

Kelly and kkards, I hear you. Casual holiday parties in people's homes where you have to take your shoes off are extra tricky. You have to take it one party at a time and decide how much you want to adhere to or defy the environmental norm. Happy to help when those specific occasions arise. Give me a shout.

Nemosmom, that sounds like "an outfit at a time" challenge, and I'd be happy to help you complete your look when you're unsure.

ChrisM, the size fluctuation an expense is a harder one. Have you tried shopping for party looks closer to the time of the event?

Stagiaire Fash

Veteran

Juniper, there is one look that always comes to mind when I think of working in formal clothes. Growing up, we took “social dance” lessons, where besides learning to Walz & chacha, etc, we also practiced things like introductions. Every week we’d line up for the boys to introduce the girls to the matron who ran the show and a guest mother while Babs White hovered gracefully in the background. I don’t know exactly what her duties were—maybe preparing snacks when we had them? But I know she was stately, with perfect posture, very white hair, a fancy white blouse, and a full-length black velvet skirt. There may have been some variation on the skirt color and even an occasional plaid, but they always went down to the floor, had pockets, and were simple A line cuts. To this day, when I think of elegance, she is my mental image. Would something like that work for you? These days, of course, you could sub tuxedo pants for the skirt if you wish.

gryffin

Veteran

I just finished redoing my dressy capsules. For me the awesome black suit carries me though most of life. I have a difficult time finding tops I like that work with suit jackets. I have a few but could use more because I can wear them with less dressy pieces. The LBD was a killer to find. I'd still like a very dressy shift dress. But I have sufficient dresses to cover for now. Flat very dressy shoes with pointy toe, black, comfortable, must take an orthotic (you see the issue) are my hewi or be so supportive I can go without. I bought the TS gown in advance of black tie because I can do Le Smoking fine but I just don't like dancing in a pants. If the party has dancing I will always choose a dress. It's a girl thing!!! ISO flat pointy comfortable very dressy shoes and very dressy shift (in case I'm not feeling sheath svelte)

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Stagiaire Fash

Veteran

Sterling, what about that beautiful Ted Baker scarf you showed us a while ago?
In other posts you’ve shown a beautiful velvet dress that you didn’t get, mentioned that you wear black tights in the winter, and said that instead of sneakers, you like loafers and oxfords these days.

Here’s what I think your winter festive capsule should include: that scarf, a velvet /velour T-shirt in a color that goes with the scarf (fuchsia. Go Fuchsia), dressy black wool trousers, a more casual bottom, a dress in one of the gentler colors in the scarf, a close-fitting warm undershirt, black tights, and dressy black (patented leather?) or metallic loafers.

Would you feel like yourself in that?

ETA: no fuchsia here :(. https://m.shop.nordstrom.com/c.....6_60132457|60132456_60132463&flexi=8000544_60188287|8000544_8000557|8000544_60187716&flexi=60135057_60135059&flexi=8000485_8000526

Maybe a coordinating lighter shade of pink or a fuchsia silk blouse and velvet bottom?

rachylou

Veteran

Angie’s double-hose trick is the ticket for me. Best tip ever.

Sal

Veteran

I enjoy occasion dressing but most of my occasions happen in summer which makes it a bit easier. I think there is a wide range of looks that are appropriate for most events such as Awards nights, weddings, staff functions, oarties - true black or white tie events are quite rare here.

I think elevated fabrics, dressyshoes ( flat or heeled) and a good bag are the key points. Doc Maerins could work if they are shiny and worn with the right skirt or pants.

I mostly like a dress but I would love a dressy pant suit in an ideal world as well.

anchie

Veteran

I don’t have a problem with a very dressy events like weddings or balls where the rules are clear, cocktail dress for the wedding or gown for the ball. My challenge is the events that a just a little bit dressier then everyday wear, like party at a friends hous, dinner in a nice restaurant, theatre or exhibition, date night, or drinks with girls. I never know what to wear, and always feel underdressed, especially in colder months.

Gigi

Veteran

In case it helps anyone else, a couple things that help me in the deep winter when I need to be dressy but warm in a dress/skirt are OTK socks and silk long underwear for my bottom half.

I will put on the hosiery I plan to wear with the outfit (I usually wear microfishnets), and then I will put on top of that either thick OTK socks or the silk underwear. I then take off the socks/underwear when I get to the venue.

Socks would require a larger bag to stash them in, but the silk underwear doesn't take up much space and could easily fit into a medium-sized purse. You can wear daintier footwear with the silk underwear; the OTK socks would require a larger shoe or boot because of all the fabric from the sock.

The long underwear I have is from WinterSilks, and it is just a lightweight, simple legging-type garment in solid black. So it doesn't look obviously like long underwear.

Stagiaire Fash

Veteran

Rachylou, you mean 2 pair at once, one on top of the other? I agree, that is surprisingly helpful when it’s cold out.

Runcarla

Veteran

My problems with occaision dressing disappeared when I developped a dressy capsule that covers a range of occaisions from black tie to house party. What helped me be comfortable in occaision wear was to stay true to my 'tomboy' moniker and find sporty wear in luxe fabrications.

https://youlookfab.com/welookf.....over-items

Last week I wore my favourite black trousers with sweatpants styling, a wine coloured slouchy sweater, and my silver Converse sneakers to bridge. i got two compliments on my nifty sneakers!

With a mix and match capsule, and no scruples about outfit repetition, I might splurge on a mani and pedi, or time with my stylist for a polished 'do.

Helena

Veteran

Dressy for me is tough, even though it generally only calls for smarter shoes and tops with my jeans or black skinnies ... Because our dressy nights are rare, probably one per season ... So that means different shoes, tops, accessories due to weather etc ... But I don't want to waste a ton of budget on something that will rarely be worn! So I end up with cheaper pieces that look as such, or trying to dress up my regular wear. That's my dressy challenge!

Stagiaire Fash

Veteran

TG, i hear you on that. These occasions are even less frequent for us than you mention. I tend to have several options of what to wear for them in the back of my closet. I pull them out occasionally, wonder why I don’t wear them more often, and return to not having dressy occasions. If I was to buy something “fancy” these days, I think it’d be pieces I could wear with other things, casually, and then, when I give the signal, assemble into a dressier look. Can you do that?

Cardiff girl

Veteran

Oh gosh where to start!l always feel that I look a lot older in occasion wear,matronly,is the word..,which I don’t feel when I m wearing my usual style.I struggle to fit dresses anyway so that doesn’t help.l think that it’s really tricky these days to hit the right note as one persons smart casual is another’s haven’t bothered .Then there s the stress of spending money on something that I m unlikely to get much wear out of.l could go on!

Anonymous

Thank you, Fashintern. Those are excellent ideas.

nemosmom

Veteran

Thanks, Angie!! I would unfortunately have to shop for a clutch to go with any outfit before I could get feedback. I guess that’s where I get stuck — I don’t even know where to start.

unfrumped

Veteran

Sterling, might’nt you like something like the jumpsuit?! It’s like drssy trousers. That helped me feel” authentic “.

Hmm- all the usual suspects for me. Need closed- toe footwear but not clunky, hence can be harder to look dressy and be comfortable. I know there are options/ compromises, but I want to look like the fashion magazine party pages!! With dresses I usually want a bit of heel, but those are hard.

Warmth- yes.
Dresses with enough length- yup. Sleeves! Colors that are not black.
Keeping a capsule at the ready but not getting outdated- yes. Different seasons- hard somehow for me to have things that would work in any random time of year.

I mostly am referring to very dressy events. Other sorts of “ festive” but more casual, I don’t worry as much.

rachylou

Veteran

FashIntern - yes!

Helena

Veteran

Fashintern, yes, that's my current trick ... A black shirt that can kind of go different ways, and be 'glammed up' a little with a red lip or a statement earring. It always feels a little boring though beside some other friends who really go for it with dressy stuff ... But perhaps that is the optimal solution for me and I should just stick with it!

Joy

Veteran

Dressy for cold weather used to be a problem but I have slowly added some pieces that have worked well for me. The black tux suit is one. I wear it most with a black, red and white sequined sleeveless top, and am still looking for the perfect lacy or satin off- white top to use with this. Other winners are fancy bottoms like a black wool beaded skirt or festive plaid or metallic pants with a simple sweater, usually a turtleneck, and maybe a silk or velvet jacket.
I have some long skirts in black wool, jersey and velvet. A velvet top, and a long beaded tunic made in India with a beaded paisley design that works well over a column of black ( pants or skirt) and gold jewelry. Any of these can be worn with boots or booties, but I also have pointy toe kitten heel patent pumps. Nothing seems to date as long as I have the right footwear.
For more casual times when it is cold, I like metallic jeans with a sparkly top and a jacket or a cashmere sweater, and boots or booties with sparkly socks.

Gretchen

Veteran

I have 2 problems, which are related:
1. Buying new when it’s a special event, and then having closet orphans (I have 4 cocktail dresses, and have maybe 1-2 events/year where they would be appropriate).
2. NOT buying new, and then wishing I had party shoes, or the right pair of earrings, etc. I hate having a great cocktail dress paired w my sensible Tuesday pumps.

gryffin: love your dressy capsule. Maybe I’ll steal that idea and look for some holiday bargains.

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