When the Invitation Says “Cocktail Attire” (But You Don’t Wear Dresses)

Maybe it’s a wedding. Or a 50th anniversary. Or a fund-raiser for your best friend’s favorite charity. The invitation says “cocktail attire,” or something equivalent. If you’re like me, the feeling of anticipation is mixed with dread, as the idea of having to shop for (and wear) a dressy dress makes you break out in hives. So I’ve come up with some outfit ideas with pants that can pass “cocktail” muster, but won’t require shapewear or self-tanner.

With so many of us living more casual lives these days, navigating dress codes more formal than “smart casual” can be particularly challenging. Our mothers may have maintained wardrobes to accommodate specific dress codes and levels of formality, but I know very few women today who do.

I’ve been following Amy Smilovic (Founder and Creative Director of Tibi) on Instagram for a while, and subscribe to her newsletter. I really like her approach to personal style and wardrobe building. She talks a lot about the importance of feeling like oneself in one’s clothing. Wherever you go, whatever you do. (She calls it a “through line.”) And her approach to wardrobe building is similar to mine, which is to create a versatile, cohesive wardrobe, that can accommodate just about anything life throws at us.

When Manina and I did an Instagram Live last year to talk about Gamine Style, one of the questions we addressed was how to put together a more dressed-up look. For those of us with more casual, relaxed, or androgynous style, a standard “dressed up” look can often feel too fussy or “trussed up.” So we might have to think outside the box a bit, which is what I’ve done here.

A slightly unconventional approach to “cocktail attire”

Susan B. wears a custom silk tuxedo shirt with Tibi silky cargo joggers and strappy slides, and carries a small aqua Loewe Flamenco bag.

To create this look, I shopped my closet, and I really love how it came together. It feels dressed up, but still relaxed. Comfortable, a little quirky, and I feel very much myself in it. The top and pants are both in a silky fabric, which adds a luxe factor. But the difference in textures keeps the outfit from looking flat.

The top

The silk tuxedo blouse is a custom piece I had made a few years ago by Amanda Thompson Couture in London. I’ve always loved the somewhat louche appeal of a tuxedo shirt, worn slightly undone. Here’s a minimalist version from Me+Em, and a more relaxed linen style from Free People. Or check the men’s/boy’s departments at your local thrift store…I’ll bet you’ll find some good ones there.

The pants

The pants are those same silky cargo joggers I packed and wore in London. They’re a bit unconventional, but I find them easy to wear and style. These from Ruti have a similar look (and the price is 40% less). Here’s a style from Cinq à Sept that’s available in several colors. A fuller-leg and more relaxed style from Eileen Fisher. These from Cuyana are good too.

The accessories

Detail: Susan B wears strappy kitten heel sandals.
My sandals are from a prior season and no longer available. Here are some similar styles that could also work:

I believe that accessories can do a LOT of the heavy lifting to dress up a look. Especially when the clothing is simple. I’ve added a pop of color with the bag, which also has a shoulder strap so I can go hands-free. A pair of statement earrings would be good with this outfit; I’m on the lookout for some with a minimalist vibe that don’t weigh a ton.

While I’d happily wear this to a “cocktail” level event, I know it might not pass muster in every locale. But I think no matter your region, having items in your closet that can dress up or down is key to getting the most out of your wardrobe.

More “not a dress” ideas (cocktail outfits with pants)

Here are two looks, to give you more ideas. For each of these, I included pieces that could be worn separately, and styled for a variety of looks.

"Cocktail attire," but make it relaxed. Teal Eileen Fisher tunic & pants, gold strappy sandals, gold & pearl jewelry, raffia clutch.
(Top is sheer, here’s a matching silk tank to wear underneath.)

“Co-ords” (matching top and bottom) have been a big trend for the last couple of seasons, and they can be an easy way to create a pulled-together look. What I like about these from Eileen Fisher is that the top and bottom textures are different, which creates visual interest without interrupting the clean lines.

Here’s another option, this one in a cool palette. Sparkly jewelry, a beaded bag and metallic sandals dial up the simple top and pants. (Both of which could be easily worn in more casual outfits.) I’ve shown the pants in navy here, also available in black.

So when that invitation arrives, don’t feel you have to start panic shopping for a dress, if you don’t wear them. A cocktail outfit with pants is a workable alternative, and chances are you already have some (or all) of the components in your wardrobe.

Tell me about the last dressed-up event you attended. What did you wear and how did you feel in it?

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  1. I love these ideas and your outfit looks great! I do struggle with this type of dressing as a natural/classic Summer, any ideas for a MOB or MOG outfit especially for this upcoming November? Thank you for all of the lovely posts, I look so forward to reading each one!

    1. Hi Marysue, thanks! As the fall styles start to roll in, I’ll be keeping eyes open for more options.

  2. I find palazzo pants the perfect answer to dressy events. I have them in linen, satin, blends, and even a sequined pair (BR, bought the first year of Covid for New Year’s Eve at home). They are comfortable, and can be dressed up or down depending upon footwear, jewelry, and the style of top.

    1. Those were my first thought as well. Add a dressy top, some jewelry, and you are good to go.

  3. In a black wool crepe skirt suit and heels I am the Queen of Sheba but also myself at the Paris opera, do not begrudge the baggage space. I like your suggestions and act on some but on this issue we are far apart. Long live choice!

  4. Hi Susan–it’s like you’re reading my mind. Or maybe we’re in the same ‘zone’. I have an art show coming up in 2 weeks and I’ve been stressing over shoes, of all things. My Vince heels that I’ve had for years and hardly worn aren’t really the ticket so your Jeffrey Campbell find looks like it might be just what I’m looking for. I loved the Tibi cargo pants so I got them! I’ve been reading Amy also and liking her attitude toward dressing. I also like that she had models who have different body types, showing that her clothing line works for many figures. When Amy wrote about mixing textures of clothing so that you don’t look ‘boring’, that rang a bell: when I’m head to toe in EF linen, I feel a bit frumpy–but now I realize that I need different textures/proportions or layers. I’m certainly a ‘no dress’ girl (mostly, although I have a couple of linen dresses from Eileen Fisher), so the silky cargo pants are a yes for me. Thanks so much!!

  5. The overly casual style of the pants cancels out the silky fabric, so the overall look seems wrong. It doesn’t look pulled together to me.

  6. My last dressy event was my daughter’s wedding, which called for black tie. As a casual but classic 60-ish woman, I wasn’t prepared and let myself be talked into a dress I was not comfortable in. I cringe when I see the photos, and really regret not being more proactive in insisting on wearing something that suited me better.

    You say, “The difference in textures keeps the outfit from looking flat.” This is something I intuitively knew, but had never heard stated. Thanks!

    Finally, self-tanner. Ugh. I have very pale skin and am sick of people commenting on how white my legs are in the summer. I’ve finally learned to smile and say, yes, that’s because I’m Caucasian. That shuts them up, LOL.

    1. Thank you. These fabrics are lovely and the designs are simple, and I hope, becoming for a Petite.

  7. Love this! The silky tuxedo top worn loosely with the slouchy yet elevated Tibi joggers is chef’s kiss – contrast and complement at the same time. Just your style, always fun, always interesting. It’s the reason I look forward to reading your posts with my morning coffee, and have for so many years.

      1. I like the outfit, but not sure I could pull off the blouse with so many buttons undone at the bottom. I think, on me, it would look as though I purchased a size too small. Perhaps it’s because I’ve never seen a blouse worn that way, wondering what your inspiration was, Susan? On another note, the final season of Seaside Hotel is now available on PBS Passport. Thanks so much for the wonderful recommendation, a while ago!

        1. Hi Marilyn, The shape of the blouse with the bottom buttons undone was intentional, to keep it from looking oversized and boxy. And yes, I’ve been watching Season 10!

  8. I love this look. I totally understand that it won’t be everyone’s “jam” and won’t work for all dressy occasions. But, for me? it rocks! And thanks SOO much for the closeup of shoes. It shows where the pant is hitting. I struggle with the length of joggers so big help.

  9. I still love a dress and love to wear a dress. But I won’t buy one for just one occasion. I have a few versatile pieces in my wardrobe. Skirts too with silky tops. So I would be good.
    LOVE your outfit. You’d fit right in.

  10. I love this outfit–I’ll have to shop my closet for a top. I think statement earrings would be fabulous and I think I might try a pair of chandelier earrings I have that made it (slightly damaged!) through the Tubb’s fire in 2017. I’m always looking for edgy earrings–let me know if you know of some good sites for looking!

  11. Well I love the CPShades tuxedo shirt in linen and the silk utility pants! Great for many occasions. But I’m a far cry from Gamine so your suggestions would not work for me in a cocktail or dressy occasion. It would be fun for you to explore other style types and color palettes that suit the rest of us. Good topic!

    1. Hi Leslie, I’ll be working on more of the Style Profiles in coming months, and will do my best to include some dressier outfit suggestions.

  12. I’m OK with the outfit and it’s probably great for certain ‘cocktail attire’ gatherings and maybe not for others…..have to know the setting. But I’m confused about joggers….I thought they should be snugger to the ankle so I must be off base. Love the color choice for the bag but think a smaller bag with a real cocktail/evening vibe would be best. Are the shoes comfortable? I have shoes that are 4 hours max and then it’s time to leave 🙂

    1. thanks, Dee. I haven’t worn these shoes for longer events, but they’ve been comfortable so far.

  13. Love those choices! Can you suggest comfort shoes that can appear more dressy? I can’t wear heels and need flat shoes with arch support?

    1. Hi Michelle, I’ll be doing a few more footwear round-ups for summer and will be sure to include some comfortable + dressy styles.

  14. Excellent post! I actually had a cocktail event a few months ago and opted for a black one piece jumper with gold jewelry and apparently accidentally found a winning combination based on the compliments I received from other attendees which made me incredibly happy because it’s been awhile since I had to attend an event with 450+ folks in attendance!

  15. LOVE. THIS. Thank you, Susan! I experience the Dress Dread, too. For me, it’s something about the combination of being 1) very short, and 2) in my 70s. I just can’t make dresses look sharp anymore. And the selection of petite proportioned dresses is pitiful. Your outfit here is perfection.

  16. I guess I’m the odd girl out here. I love to buy a new dress for occasions, boho leaning, maybe, but still a dress!

  17. Susan, you look great in that tuxedo blouse! My favorite cocktail attire is an oversized white tuxedo blouse and black cigarette pants! Great post!

  18. I really don’t like dresses either Susan. I force myself to wear them! I do love a long skirt and or pants. Love the idea of the silk cargos!

  19. Fantastic outfit, Susan, and great advice in general about selecting an outfit where one feels like herself. I might switch out the bag for something a bit more glitzy for an evening event; otherwise, I think it’s just perfect and, most importantly, so YOU.

  20. What a great outfit, Susan! This would work great on almost any ocean cruise to elevate ones dinner outfit from the ubiquitous black pants + shirt one so often sees.

  21. I think your outfit looks great; so creative. Actually don’t even own a dress, Have even worn dark black jeans with a slightly wider leg with a fancy black blouse tucked out, so you can’t tell they’re jeans. I have a lot more fun if I’m comfortable. I find that a classy evening bag ( have an ancient Chanel evening bag} and interesting jewelry can make that outfit look very chic.

  22. Lovely outfits but I must say I’m Team Dress. The last time I wore one was earlier today to a garden party. I’ll use any excuse to wear one. I find them comfortable, effortless and chic. That’s me though and doesn’t need to be anyone else.

  23. I hardly ever wear dresses. I have many dressy tops, some are Asian-inspired from Citron Clothing in LA, others are hand-painted silk stand-neck blouses from an artist in LA who I met years ago at the American Craft Council show in San Francisco. I wear black Eileen Fisher trousers or something similar and lots of interesting jewelry.

  24. I agree – trousers are a perfectly acceptable alternative to the traditional cocktail frock and, to me, gorgeous shoes and knock-out jewellery show you have put in the effort. Nothing is worse than being uncomfortable in a situation where you should be able to radiate a merry and sociable presence (because that’s the point of a cocktail occasion, surely?). And a good shirt works wonders.

  25. Thanks for this post Susan…while I love dresses on others they are not for me…the outfits you presented are gorgeous for more formal events. Elegance combined with comfort…

  26. I am afraid, whilst I like the silk cargo trousers, it would be a struggle for me to think of the outfit as cocktail wear. Went to a very grand 70th birthday dinner earlier this year, think dinner jackets, evening dresses. As I have little need for the latter these days, I hired the evening dress for the dinner.

    1. To me, evening dresses sounds more “formal” than “cocktail.” But in that case, renting is SMART. (I rented my wedding dress and never regretted it for a minute.)

      1. @Susan. Wore a bevy of ‘cocktail’ dresses a lifetime ago when in the RAAF. Trousers were banned (in the Officers Mess for females). They were usually knee length silk dresses paired with ankle breaking high heels and of course, stockings. As I love dresses, I would wear something similar these days, but would ditch the very high heels and probably the stockings. Not a dress wearer, then soft flowing trousers paired with a similar fabric top and some blingy flat shoes would fit the bill as well

  27. I recently went on a cruise by myself (recent widow too) and wanted to look “dressy” without wearing a dress. I wore a JCrew crew neck sweater with sequins in Navy. It packed well and is even washable, though I haven’t washed it. I wore it with pointe navy travel pants. I brought a sheer shawl in navy in case it was cold and carried my Lo&Sons Waverley bag.

    Palazzo pants are a bad memory from my teenaged years, but I think I should try some on to get a fresh look at them.

  28. For the most part I wear pants. My go to is a black silk shirt and black pants. There are times I do wear dresses. Summer is one. A linen shirt dress and or a linen wrap dress-which can actually look dressy are my go to for nice but casual outings. For nicer occasions I have two silk wrap dresses one black and one a bright navy. No self tanner for me. It turns out to be a disaster. We’ll just have to overlook my paleness. It doesn’t bother me.

  29. I am also Team Dress. I love wearing a dress or skirt especially in summer. To me, a dress is effortless, comfortable, and chic.

  30. Love every detail of that tuxedo shirt outfit!
    You have so many creative ideas about to put an outfit together!
    Love your blog!

  31. Hi Susan: who the is sandal designer for the sandals you’re wearing? I like the square toes— Vince seems to have the closest dupe