There's no wrong time for a dress as far as we're concerned, especially with so many long-sleeved options [1] that look cute with sneakers [2] and a jacket on top, too. But what better opportunity to slip into something flowy than a special occasion?
Whether you're still working out holiday plans [3], or already prepped to reunite with family [4] to make up for lost time, we're keyed into festive season and hand-picked dresses to add to your November shopping list. There are polished pieces for work (and work parties), and tiered minis and flared midis that are perfect to twirl the night away. Ahead, check out the 20 that too cool to pass up this winter. Take a look.
Old Navy Long-Sleeve Tiered Floral Midi Swing Dress
Pair this forest Old Navy Long-Sleeve Tiered Floral Midi Swing Dress [6] ($55) with low, chunky heels for cosy fireside happy hours and holiday dinners out.
Old Navy Long-Sleeve Rib-Knit Mini Cardigan Dress
Wear an Old Navy Long-Sleeve Rib-Knit Mini Cardigan Dress [7] ($60) with boots or sneakers this fall and layer tights underneath when it gets even colder. The deep green hue would be especially nice for the holidays.
Old Navy Sleeveless Tiered Mini Cami Swing Dress
Not only would this new Old Navy Sleeveless Tiered Mini Cami Swing Dress [8] ($35) be so cute in the summer, adding a turtleneck breathes winter life into it, too.
Old Navy Long-Sleeve Plaid Mini Swing Dress
Sure, you're likely familiar with this pattern on matching PJs [9] but an Old Navy Long-Sleeve Plaid Mini Swing Dress [10] ($40) is festive in and outside the house in both red and white check.
Old Navy Puff-Sleeve Velvet Mini Shift Dress
We found an easy holiday outfit in this Old Navy Puff-Sleeve Velvet Mini Shift Dress [11] ($50) as it looks both comfy and chic for hours of entertaining.
Old Navy Long-Sleeve Mock-Neck Waist-Defined Midi Sweater Dress
It's only fitting that this Old Navy Long-Sleeve Mock-Neck Waist-Defined Midi Sweater Dress [12] ($45) comes in both red and green for Christmas, but the black one's a classic, too.
OId Navy Long-Sleeve Button-Down Tiered Midi Swing Dress
We're picturing the OId Navy Long-Sleeve Button-Down Tiered Midi Swing Dress [13] ($55) with a creamy cardigan for a winter day working from home or at the office.
Old Navy Puff-Sleeve Smocked Floral-Print Mini Swing Dress
This dark green Old Navy Puff-Sleeve Smocked Floral-Print Mini Swing Dress [14] ($40) makes a fresh fall pick but there's also a navy option if blue's more your hue.
Old Navy Sleeveless Fit and Flare Smocked Floral-Print Midi Cami Dress
It's not always about the long sleeves this season as an Old Navy Sleeveless Fit and Flare Smocked Floral-Print Midi Cami Dress [15] ($45) can still be layered under a leather or suede jacket when temperatures drop. This one comes in three different floral patterns, too, if wine isn't your taste.
Old Navy Rib-Knit Maxi Shift Dress
This stretchy lightweight Old Navy Rib-Knit Maxi Shift Dress [16] ($40) is a good pick for between seasons whether you like this cream or an olive or charcoal colour instead.
Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress
Swap out jeans for a super-soft, chambray Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress [17] ($55) — it even has pockets!
Old Navy Long-Sleeve Button-Down Mini Swing Dress
This Old Navy Long-Sleeve Button-Down Mini Swing Dress [18] ($40) looks casually cool with high-tops of any colour but a bright pair would really pop.
Old Navy Waist-Defined Floral Tie-Belt Midi Wrap Dress
If you don't like fit-and-flare or shift dresses, choose this Old Navy Waist-Defined Floral Tie-Belt Midi Wrap Dress [19] ($45) with an adjustable belt and tiered skirt.
Old Navy Puff-Sleeve Floral Maxi Shift Dress
The back of the Old Navy Puff-Sleeve Floral Maxi Shift Dress [20] ($45) is one you won't want to cover so pick this on a warmer fall day or a night spent indoors.
Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress
You can definitely get more than just one season's worth with this Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress [21] ($45), thanks to those long sleeves. Just slip a cardigan or denim jacket on top when it's chilly.
Old Navy Long-Sleeve Printed Mini Swing Dress
Tie the waist of this Old Navy Long-Sleeve Printed Mini Swing Dress [22] ($50) for a more fitted look, layer a roomy sweater on top for an instant skirt, or leave it loose as a tunic instead.
Old Navy Long-Sleeve Striped Mini T-Shirt Shift Dress
Coming in khaki or navy stripes, this Old Navy Long-Sleeve Striped Mini T-Shirt Shift Dress [23] ($35) gives off major preppy vibes with loafers and a blazer.
Old Navy Long-Sleeve Button-Down Tiered Midi Swing Dress
Grab colourful accessories, this Old Navy Long-Sleeve Button-Down Tiered Midi Swing Dress [24] ($55), and white sneakers [25], and head to a weekend brunch with friends this fall.
Old Navy Smocked-Waist Fit and Flare Cami Midi Dress
Either a teal or black Old Navy Smocked-Waist Fit and Flare Cami Midi Dress [26] ($45) can be the versatile party pick your holidays need as it can be dressed up for a fancy event or worn with slip-on sneaks or slides, too.
Old Navy Long-Sleeve Fit and Flare Tiered Midi Dress
The delicate details of this floral Old Navy Long-Sleeve Fit and Flare Tiered Midi Dress [27] ($50) would contrast so nicely with a pair of combat or other lug-soled boots (but it'd look nice with pointy flats as well).