Thinking outside the box for special occasion outfits
One of the recurring requests I receive from readers is for “special occasion” outfits and ideas. I’ll admit I’ve procrastinated on addressing this one.
Why? First, because the concept of special occasion wear has become so fluid and fragmented that everyone seems to have a different idea of what it means. And second, when I browse through the selections of what’s considered evening or “occasion” wear, frankly I’m a little turned off. So much of it reads to me as stuffy or stodgy, or looks downright uncomfortable. Or too exposed. Or overly frilly and twee.
And if you don’t often attend events that call for dressing up, you may not want to splash out on something that may only be worn again a handful of times, if at all.
So I’ve been thinking of some alternatives to special occasion dresses. I wanted to incorporate pieces that can be mixed and matched with other items in your wardrobe for different levels of formality. (Not Black Tie, but outfits that can be dialed up or down a little bit with accessories.) And that would be comfortable enough for sitting, eating, dancing.
“Outside the box” special occasion outfit ideas
I keep thinking back to Sharon Stone wearing a Gap tee to the Oscars in 1996. It’s a great reminder that glamour doesn’t have to be fussy. Yes, she paired it with Valentino and Armani. But to me that glam + basic mix is still a modern approach, and can be achieved even if you don’t have a designer budget.
I’ve put together a couple of outside-the-box special occasion outfit ideas to get you started. The first is in a warm palette (Autumn), the second in cool (Winter). You can always put your own spin on something similar with different colors, details, and accessories.
1. Midi skirt
Above, I’ve styled a slip skirt with a silk wrap blouse, gold jewelry and a sparkly clutch. You could wear both the blouse and skirt separately in more casual outfits. You can also dial up this look with metallic shoes, or add a bit more sparkle with jewelry.
The skirt is available in sizes regular and petite up to size 14. Here’s a Plus size silk top that could also work well with the skirt.
If skirts or dresses aren’t in your wheelhouse, here’s another idea with fluid wide leg pants and a silk top.
2. Pants
For this second special occasion outfit, I’ve kept everything simple, and not overly formal. I’ve used the concept of “tabletop dressing” and kept most of the interest/focus above the waist. The sheer silk scarf adds some pattern and a nice focal point. It can be tied in a loose bow, or just draped casually around the neck. (Use code SUSAN10 for 10% off Odyssey scarves.)
Here’s a similar pant, available in Petite and Plus sizes. And a similar top, available to size 3X.
As with the first look, each of the pieces could be combined in more casual outfits. Again, you can select different accessories to make the outfit more or less formal as needed.
(Yes, some of the items shown are spendy, but you should be able to easily find more budget-friendly alternatives, especially as we get closer to the holidays.)
🧳 Both of these looks should also be able to pack and travel well, another plus. ✈️
Making it work
✨ Look for simple pieces in luxe fabrics (silk, velvet, satin). Textures and accessories can do a lot of the heavy lifting to make an outfit more festive.
✨ Special occasion jewelry doesn’t have to be expensive. Have fun with the costume stuff if that’s your style.
✨ Opt for shoes that are comfortable to stand, walk, dance in. If your feet have become accustomed to flats, those 3″ heels won’t cut it after a few minutes. There are so many great choices for pretty flat and low-heeled shoes these days, there’s no need to sacrifice comfort.
More ideas for your special occasion outfit
Do you have a favorite special occasion look?
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Thanks for the ideas. I have a wedding and cruise coming up and have been struggling with the idea of dressing up for the occasions. My last cocktail type dress is just sitting in the closet and seems such an outdated idea and so unsuited to current styles and lifestyle. This was a very helpful article and will be a great guide when shopping.
I completely agree with your ideas for a pretty blouse and pants or a skirt. I remember Sharon Stone’s outfit. That was an inspiration to me also. I have a nice pair of fluid wide leg black pants that I’ve had for years. I still use a couple of pretty blouses from the past or I buy a new one if I feel like it. And jewelry. Even when I was still working, this kind of outfit worked for special occasions. Thanks Susan.
I really like the idea of using separates to create a special occasion outfit that can be used in casual outfits as well. I want to try the wide leg black pants by Eileen Fisher that you included in your post – it feels like a relief to have an option other than the straight leg or legging style pants that have been in style for so long. Thanks for including the winter palette as well as the autumn in the outfits you featured – they were both lovely but I tend more toward pants than skirts.
I love both outfits that provide a helpful base for giving me inspiring ideas along with the additional recommendations posted–thank you!
I absolutely love the second outfit..the colors just “pop”, and I think would work for me…a dark Summer. ( winter colors are too washed out…soft summers work, but this green is lovely).
I took a cruise in May on Silversea, and they had two formal nights; the rest of the dinners were “dressy”. I used this formula for the dressy nights…dressy pants with special tops ( some silky, some sparkly ) and always felt well dressed. I did wear a gown for one of the formal nights ( the men were in tuxedos).
A timely post! I’ll be taking the Queen Mary to England this fall, and two of the evenings aren’t just gala but “themed” (ugh—not the reason I signed up for this!). I recommend vintage and resale for this sort of once-in-a-blue-moon situation. I’ve been having pretty good luck with TheRealReal, where the prices are reasonable and I can filter for exactly what I want. A friend whose daughter recently got married found their couture gowns at an upscale vintage store in L.A. The bride wore bright yellow and looked smashing!
We will be returning to the UK on the Cunard Queen Mary in October, I wonder if it is the same the sailing?
It’s the October 7–14 crossing. Maybe we’ll meet!
I cannot remember the last occasion I had to dress up for. Those years are behind me. We used to have a gala every year when I worked and was mid thirty. Going all the way. Long gowns and such. I loved it but it was expensive.
Nowadays I think: “I bet I can find something suitable in my vast wardrobe” haha.
Greetje
Such a great post. I feel inspired. (And, I purchased the Sarto flats in the gorgeous green — absolutely beautiful, thank you!)
As for this: “Special occasion jewelry doesn’t have to be expensive. Have fun with the costume stuff if that’s your style.”
That made me smile. Every week, I get compliments on my “diamond studs.” They’re $15 CZs from Nordstrom Rack. 😉
Great post, even though I have no formal occasions on my calendar. What I do have is some nice black wide leg Vince trousers and an array of silk blouses. Two of those blouses have teal in them, so I’m also ordering the Sarto flats in green. Plenty of jewelry to complement such an outfit, now all I’ll need is someplace to go!! Life has gotten so casual these past couple years.
I hope you;re enjoying some restful time this month!
Silky top and pants are my “dressy night” go-to when I’m traveling. One pair of pants is plenty for the whole trip. My issue with wide leg, flowy pants is that you need to have a more fitted top or you end up looking like a clown in oversized clothing. Most of my silk tops are tunics so I go with straight leg or skinny bottoms. Would you tuck in the teal silk top here?
Yes, you could tuck it in, and wear the scarf as a belt/cumberbund.