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 XX-Small to 3X, and in several solid colors as well. 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