How I Transition 3 Summer Dresses and Make Them Fall Ready

Like many of you, I wait as long as possible to pack away my summer pieces, just because it’s a lot of work and I dread it. Though I like fall fashion, I don’t like the rotation that has to take place. So to put off the summer exodus I’ve thought of ways that I can wear a few pieces that I loved in summer, in the fall. The 3 items I’m focusing on today are all dresses, but this can obviously be done with skirts and rompers.

First up is my long sleeve t-shirt dress with the baseball tee hemp. It’s a medium weight, so it didn’t feel heavy in summer though I wouldn’t wear it on day when the temperatures were soaring. So I can work in a few over pieces to add warmth and it will do well in the cooler fall temps.

The first outfit is good for a day when it’s a little cooler and the air feels a bit crisp. No frost on the ground yet but feels like it might be soon. I’ve thrown my green spring jacket over the dress and added some combat boots that are a little scuffed up. This has a casual comfy vibe to it, perfect for a day when you don’t want to do too much with your outfit. If more warmth is needed then a scarf can be layered over the dress.

Black Long Sleeve Dress | Casual Look with oversized coat, combat boots and scarf

Next up is my ‘ready to take on the world’ outfit. Otherwise known as an all black outfit, which I love. I’m using a heavier black jacket that is well suited for fall, I’ve paired this with my black knee high boots for an overall bad ass vibe. I would probably add tights with this along with a scarf because I know I’d be cold otherwise. This outfit is great to wear on day where the winds might be a bit stronger.

Black Long Sleeve Dress with Faux Leather Jacket and Black Knee High Boots

This last outfit is good for those fall days that are on the warmer side. I’ve just paired the dress with an oversized scarf and some booties. Again tights may be added if more warmth is desired or needed. I’ve thrown in a wide brim hat just because I love hats and think that it goes great with this outfit.

Black Long Sleeve Dress with knee high socks, black booties, a scarf and hunter green floppy hat

Black Long Sleeve Dress with black booties and messenger style hand bag

The next dress is more on the dressy side. It’s a hunter green midi dress. The fabric isn’t that thick so adding layers is definitely needed when wearing this for fall.

First up, I’ve paired the dress with a chunky grey grampa style cardigan, to tone it down and make it a bit more casual. I’m also going to wear some cute black flats with it. Because this is a midi dress I don’t want to wear any shoes that are past my ankles, just because I feel that it will make me look shorter.

Green midi dress with grey grampa style sweater and black flats

The next outfit I put together is with a beige trench coat. This is a great choice on days that are cooler. The coat also adds some polish and elevates the overall look. A pair of black booties and a structured purse would complete the look. Even though I’m not going to any business meetings, if I were this would be a great choice.

Green midi dress with flared tan trench coat, black booties and black hand bag

Green midi dress with flared tan trench coat, black booties

I couldn’t resist adding an outfit in here that highlights the cut of this dress. I’ve paired this hunter green dress with a vibrant fuchsia scarf, along with a deep purple kimonostyle cardi and the ever elegant black strappy heel. This is of course best suited for a warmer fall day.

Green midi dress with purple kimono style cardigan, fuchsia scarf and black strappy heels

The last dress in the line up is a gorgeous navy blue. The dress does have a lining so is a bit on the thicker side. It does hit me above my knees so tights or knee boots would be a good choice to add when wearing.

The first outfit would be great for a dinner out or a work function. Using the dress as a base I’ve added a long black cardigan to provide some additional warmth along with this I would wear my black suede boots that reach just below my knees. With the boots and the cardigan the look as overall elegant feel to it.

Navy dress with oversized blazer and black knee high boots

Navy dress with oversized blazer and black knee high boots with a scarf

Next up on the docket, I’ve combined my red cashmere sweater, because I love the contrast of red and navy. I would layer the sweater over the dress, creating a sweater and skirt look. Tights and heeled booties would be thrown in to complete the look. If the day is on the cooler side I could wear either my black leather like jacket or the lighter weight green spring jacket.

Navy dress paired with a red cashmere cardigan, knee high socks and black booties

Navy dress, red cashmere sweater and faux leather jacket

The last outfit is another colour pairing that I like which is tan and navy. I would wear this on a rainy fall day. I’ve paired the dress with my over the knee tan leather boots and have pulled out the trench coat once again. For some added colour I would throw in my hunter green scarf along with my green wide brim hat.