What to Wear: Summer Dresses in the Fall

I’ve got something of an addiction to black opaque tights. Every morning, I want to wear black tights with a dress or skirt. It’s a great way to transition between the seasons. Here is Anne’s request:

How do I wear this dress?? It is by Plenty Tracy Reese – it’s made out of a very soft cotton and silk material that has a little bit of sheen but is not too shiny. I’m not very good at accessorizing or adjusting things for different seasons – this dress seems a little spring and summery to me, so how could I wear it in fall and winter? I figure there has to be something more interesting than the plain cream cardigan or pashmina that I have.

I’m having the same issue with a dress I just bought at Forever21 – it’s a burgundy red tank dress with bubble hem and empire waist – the weather is not so appropriate for it now by itself, but is it possible to wear these kinds of dresses over a long sleeve top or with tights? I see these looks in magazines all the time and it looks very cute, but on me it looks a little silly so I’m wondering if I am choosing the wrong things. Or maybe I don’t know how to dress for my body type (five feet tall, small chest but with a wide ribcage and shoulders – I inherited my dad’s short stocky soccer body.)

This dress has a great color palate for summer and fall. As a first step, I would consider having the bubble hem switched to a more timeless, flexible straight hem by your local tailor. As for wearing a shirt underneath, that’s tricky and would probably require some sort of bodysuit top and that just brings up all sorts of bad junior high memories. A little clever layering on top and you can wear the dress for a couple more months.

Dress – Anne’s own.
Sweater – A navy cardigan really plays well off the brown and cream dress.
Belt – A wide belt will help to keep everything together and feeling tailored.
Shoes – A brown heel with a little flair and lot of substance.
Tights – Nude fishnets are my secret weapon. They don’t have the va-voom of regular fishnets or the stodginess of regular hosiery. A little extra warmth!
Earrings – From Forever21.
Clutch – Grey fabric wristlett from Etsy.

If it got really cold, you could even do this with boots and a cropped jacket over a sweater.