How to Wear Summer Dresses in the Fall and Winter


Hi everyone, it’s Emily! 

Boyyy is it hot outside!! High summer in SoCal has me wanting to wear a bathing suit everywhere, but with the way 2022 is flying by, I know cooler weather will be here before I’m ready for it. 

It kinda feels like I bought summer clothes and there was about a week long timespan when it wasn’t too hot to wear real clothes (like actual clothes other than tank tops and shorts). Being able to style your summer clothes for winter is more eco-friendly, less work for you (since you don’t need to pack up the items), and forces you to be a little more creative with styling your outfits. :)

So how can we maximize those summer clothes, whether they are new or old, and get the most use out of them? I’ve put together 3 tips for how to wear your summer clothes in the cooler fall and winter seasons.

#1: Layer, layer, and oh yeah… layer!

This one seems fairly obvious, so I’ll get specific here. 

Remember those floral-ly, brightly printed maxi dresses you wore almost everyday in June? (They are so trendy this season!). Pair a jersey turtleneck under those spaghetti straps for a quirky, yet fashionable look. 

handkerchief dress with turtleneck - style blogger

Using my pattern mixing skills from my blog on prints!

Turtlenecks also look great with a slip dress:

slip dress with turtleneck - slow fashion blog

In fact, you can pretty much layer a turtleneck under anything. Check out this cute tee/turtleneck combo:

tee shirt under turtleneck - handmade clothing blog

One rule: the tee shirt can’t have too tight of a neck or you’ll start looking like an actual turtle, and it will be quite uncomfortable.

Layer an oversized blazer over your mini dress or skirt. There’s something about a blazer that just says: "Fall". Maybe it’s the back-to-school vibe?

oversized blazer - slow fashion blogger

You can also cover up that mini dress/skirt with a long or oversized cardigan!:

cardigan over romper - style blog
Can you tell I didn't have time for an iron? :'D

Leggings under your mini skirt or shorts you ask? I say go for it! I def did this circa 2007:

marc jacobs skirt - style blogger

Scarves are one of the easiest layering pieces to apply to your summer clothes, but definitely add a cardigan or jacket to go with it!

fall fashion - slow fashion blogger

#2: Pair with accessories/shoes made from Fall-ish textiles and/or prints

Suede shoes can make any summer maxi dress turn into a fall, boho look:

boots - fall style blog

Anything leather!:

leather style - fall style blog

Check, houndstooth, Glen plaid (a few of my favorite things) scream fall/winter, so pair your summer-y tops, shorts, and dresses with layers and accessories in these pattern families:

plaid style - fashion blogger
plaid jacket - fashion trend blog
houndstooth fall style - fashion blog

#3: Add tall boots

A surefire way to get your look to pass for fall/winter is to pair it with tall boots. So swap out those platform slides for this classic fall favorite!

tall boot for fall - fashion blogger
fall style blog
cool weather style blog

Comment below how you plan to wear summer styles in cooler weather!

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