Wear Now, Wear Later: How to Transition Summer Dresses into Fall

With all of the end of summer sales going on right now, there are tons of great summer pieces that can be snatched up for a steal. However, I’m always annoyed when I pick something up and can only wear it for a few weeks before it has to sit  in the back of my closet until next summer. So to help you avoid that, I’m starting a new series here called “Wear Now, Wear Later,” with ideas on how to wear your summer pieces into fall and tips on purchasing sale items that will work for all seasons.

This edition is all about dresses. There are a million kinds of dresses out there, but knee-length ones are my staples this time of year. I’ve made myself a few shift dresses and refashioned a few fit-and-flare ones and have been wearing them all summer long. Let me show you how I’m wearing them now, and then how I’ll be wearing them later.

The Fit-and-Flare Dress

These dresses are so figure-flattering and create a perfect A-line shape that makes any woman feel amazing. Choose solid colors or basic patterns (like stripes or polka dots) so they can transition easily into different seasons. While drop-waisted dresses are coming back in style, they might be short lived so I’d stick with a classic cut where the waistline falls at your natural waist to ensure you can wear it for years to come without looking dated.


Wear Now: Summer Style

During the summer I love wearing them by themselves for an easy and effortless look. Throw on a pair of flat sandals for the day and a pair of heeled sandals in the evening, and then dress it up or dress it down with statement or delicate jewelry.


Wear Later: Fall Style

During the fall, make your dress work overtime and turn it into a temporary skirt by layering a fashionable sweatshirt over top. Bonus: The extra layer up top keeps you warmer during those cool days! Pair it with your ankle boots or knee-high boots for a cozy look and add a scarf if you need a bit more warmth.


The Shift Dress

Shift dresses are a staple in my closet and are the perfect dress for any occasion. I love that I can throw it on with sneakers, flats, sandals, wedges, or even stilettos and they’re all appropriate. Since the shape is so basic, you can have a little more fun with these dresses. Go for bright colors or patterns, embellishments, or chic edging. Sleeveless, short-sleeved, half-sleeved, or long-sleeved styles will all be in style forever, so choose whichever you’d like.


Wear Now: Summer Style

During the summer I usually wear these dresses by themselves, but if I’m wearing it in the evening and need some extra warmth, I throw a denim jacket around my waist for a laid back look that I can wear later.


Wear Later: Fall Style

During the fall, these dresses are perfect for layering. I threw on a chambray shirt underneath and then layered a leather jacket and statement necklace over top. Throw on some fun shoes and your fall outfit is complete!


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