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Fall Dress Outfits

Eventually, the temperatures will begin to drop, and a dress might be the last thing you reach for when putting together your autumn ensembles, especially if you don’t consider yourself a dress person. However, with the right accessories to pair with your fall dresses, you might start to think otherwise. Styling a dress for fall is easier said than done. After all, the idea of a great dress is that you can just throw it on and go. With layers to consider, styling can become overwhelming. So, as a head start, in anticipation of the cool weather, here are a few ideas on how to style dresses for the colder season.

Cool weather means layers. Try pairing a printed dress underneath a classic trench coat. Depending on the silhouette and print of the dress, and the cut and color of the trench, you can use this formula to achieve a variety of styles. A floral midi with a full-length classic coat can look just the right amount of romantic. While a shorter polka-dot frock and black trench give off 1960’s mod vibes. Or, go all business with a pinstripe shirt dress and belted cropped jacket.

If you’re looking for new ways to wear your standard shirtdress, try adding a sleek leather jacket and boots. You can get really edgy with a motorcycle jacket and chunky-soled knee-high boots. Or just bring a bit of edge with a faux-leather blazer and block-heeled ankle boots. Another styling trick that is office-appropriate for a shirtdress is donning a long cardigan, flipping the collar out, and belting the sweater over the dress. If you really want to lean into fall style, consider layering a turtleneck underneath your shirt dress with the belt and cardi combo.

Speaking of sweaters, it’s almost the perfect time to wear a chunky sweater dress. I like to wait until we have a few morning frosts before pulling out voluminous, thick knits. Balance out the shape of a roomy sweater dress with leggings or cropped jeans and sport it up with a leather jacket and sneakers. On the flip side, consider wrapping up in a sleek knit dress. A more fitted silhouette can be dressed up by throwing on a pair of heeled knee-high boots. Or pair with menswear-inspired loafers for a professional feel.

For a unique take on a traditionally feminine style, try experimenting with footwear. A puff-sleeved dress in a floral print or gingham can look cool-weather chic with a pair of black boots. When I want a tough boot, I go to the original combat-style boot. But a Chelsea boot or riding boot also works. Another way to really contrast a romantic dress is by styling it with hiking boots. Or try a long-sleeve printed dress with crisp white sneakers. Shoes are a fun way to change up the feel of a dress, and functional footwear during the colder season is essential, so don’t feel you can’t wear a practical pair of shoes with a flirty and fancy dress.

On the flip side, you can dress up more casual dresses, like plaid and chambray shifts, with jewelry, belts, and scarves. Or look for more rugged patterns in unexpected silhouettes, like a buffalo plaid fit n’ flair dress with cinching belt and delicate earrings. Pair with a blazer and patent flats for an outdoorsy vibe with a polished look. For denim and corduroy jumpers, layer with boho-inspired blouses for a contrast in fabric and print.

And while most of us don dresses to go outside, as the weather turns chilly and you find yourself indoors, consider a classic slip dress for lounging at home, paired with cropped knit, woolen knee socks, and a pair of moccasins. There’s never a bad time to wear a dress this fall; well, probably not on a hike, or camping, or hunting, but for your every day, consider switching things up and reaching for a dress. Oh, I typed too soon; there are dresses for hiking. Thank you, Internet!

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