Flashback Friday: Favorite Summer Dresses of 2016, into Fall & Winter (pt. 2)

Today will be the last day of the Indian Summer we have been having this Fall. The high was 68 degrees and not only did a I wear a dress with bare legs in real life but I also shot some pictures with another Summery-feeling outfit (to be seen on the blog next week). Starting Saturday, temperatures will be close to freezing, with high winds and even snow flurries. Bring on the blanket scarves!

Hard to believe November is coming to an end and next week we will be eating turkey with mashed potatoes and stuffing our faces with dessert. Since November is also the last meteorological month of Fall and also what style magazines and style blogs consider as the end of Fall, I wanted to recap some of my favorite Summer Dresses of 2016 in this part two (you can read part one here) and show you ways, ideas and tips how to still wear some of your Summer Dresses into late Fall and even Winter. One word: layers. Scarves, jackets, cardigans, leggings and tights are the 5 crucial clothing items you need to transform them into warm, weather-appropriate outfits. This post will serve me as a guide too, since I plan on wearing mostly dresses in December in order to support the Dressember Foundation.

Dress: Xhilaration (Target).

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This Summer I wore a lot of Little White Dresses. I kicked off Summer by wearing this Gorgeous Dress in late May and having my mini me matching me in her own off-shoulder little white dress. This dress has some crochet around the hem and it paired so well with those light beige/nude espadrille wedge sandals. Add nude, camel or cognac booties and a long cardigan in brown, camel, gray, black, navy or honey and this dress would be perfect to transition. For colder weather, I would add a light-to-medium weight chambray button-down underneath it and some tights and instead of booties I would pair it with tall boots. Plus the long cardigan on top. For Vivian's LWD I would pair it with a white turtleneck underneath, a red cardigan on top, red tights and black Mary Jane fallet Flats. I can picture this outfit of hers and it would make a great holiday look!


Dress: The Limited.
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This Maxi Dress has no slits and isn't very thin. Plus since it is in navy and orange, the colors would be so easy for the cold weather. I would wear fleece-lined leggings underneath, tall riding boots (in black), with a navy or black light cotton turtleneck underneath and my shearling-collared blue denim jacket on top. For some maximum layering I would also add a long pendant necklace.


Dress: Old Navy.
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I love how this mustard-striped dress paired with all the cognac. I would not change the color combination at all. I would wear this with thick nude tights (or brown tights), my nude/tan suede laceup pumps (from this post), the same belt, a bow-tie blouse layered under the dress with my warm, long olive cardigan (from this post). The combination of mustard, camel, olive and tan is great for the colder months.

Dress: Sami+Dani.

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If you buy a LWD, make your first one an eyelet one. An eyelet white dress is pretty much the definition of Summer, fashion-wise. Now this one has a mosaic-patterned eyelet design on the bottom hem, the sleeves and on the hem of the top part (since it is an overlay style). Because of the longer sleeves, the dress will be easy to wear September thru November. I did just that recently. I paired it with a cherry-print pussy bow blouse and my pumpkin-colored suede moto jacket. I would also try it with a denim jacket, a BF cardigan, a black moto jacket or a camel leather jacket. Also for shoes try it with knee-high boots, dessert booties or wedge suede booties. I am determined to make this dress work for Winter too. Of course I would wear fleece-lined tights with it.


Dress: Merona via Target.
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Black and white is timeless. And elephant prints are fun - this dress has both. I think this dress would be great to style for the Holiday season. I love red with black+white. I would add a red beanie on top, red or burgundy tights and my black leather moto jacket. I would also add a mostly-red plaid blanket scarf rolled cozy into an infinity scarf.



Dress: Merona (Target).
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This hi-lo maxi in a vibrant shade of coral-red is one of the ones I wore on my July Vacation this year. My sweet girl Vivian wore one of her favorite dresses: this pink floral+striped dress with her flower thong sandals. I later wore this dress in early September for a Summer Wedding. Now, I definitely think this is a typical Summer dress but adding a cropped jacket, a shrug or little cardigan to it, with some nude flats or even a bootie, would make it great to style it for Fall or Winter. Vivian's fancy coral dress would be great for the holidays. Picture it with a white, cream or silver cardigan on top or even her leopard cardigan for some pattern-mixing. Since leopard goes great with red why not try it with its cousin, coral!? Of course, I would add white or cream tights to Vivi's little ensemble, too.

Dress: Spenser Jeremy.
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How much I love this bright, bold floral scuba dress. The vibrant pinks, purples and turquoise pop! Pairing it with my Orange Saddle Bag was a great idea. I wore this to work this Summer. For now I would actually keep the gorgeous-hued orange bag and wear some classic burgundy or black pumps instead. I would add a tailored black blazer to it. If it was too cool, I would add some semi-sheer black tights, or opaque black tights, too. Scuba is also a thick material which is good year around.


Dress: 3 Hearts via Target.com.

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Pastels for Winter?! Sure why not!? I would totally make this dress Bohemian for Winter. Paired with my long baby blue hooded grandpa cardigan for a tone on tone look, a pair of fleece-lined black or navy tights, my navy/royal blue floppy hat, a silky scarf tied around the neck and my slouchy navy boots with block heels. Note to self: wear this outfit (I described) soon!


Dress: Loft.
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I think out of all the dresses today this would be the easiest to transition. The deep Bourdeax/Oxblood background, the dark florals and long sleeves make it easier to transition. I wore this for a collaboration post for a Spring Wedding. For Winter, I would pair it with my burgundy fleece-lined leggings (to create a monochromatic look), my nude fur coat, a black cashmere wrap scarf and a black+white marled beanie. It would look so cozy and slightly Boho.

I hope you enjoyed this fun flashback post today. Which of these dresses are your 2 favorites and do you have any other ideas for me, how to style them into the colder months ahead?! Thank you and have a great weekend!