What To Wear Between Summer and Fall

Most women find the gap between the warm summer months and the cooler fall season the hardest time of year to figure out what to wear—myself included! When it comes to bridging it, there are two things to keep in mind: practicality and aesthetics.

Choosing clothes and accessories that can adapt to fluctuating temperatures (chilly in the morning and sweltering at noon) is the most important thing. But I also like to make sure what I’m wearing hints at the change in seasons ahead.

Since the in-between of summer and fall presents such a challenge, today I’m sharing tips to build comfortable transitional outfits with ease, plus 10 shoppable outfits to wear between summer and fall that should help you get started.

What To Wear Between Summer and Fall

The good news is that you don’t have to completely stow away your favorite summer pieces yet or revamp your entire wardrobe to do transitional style well. Below are creative and practical tips to make it easier to transition your summer looks to fall.

How to Transition Summer to Fall Outfits

Add Layers

Layering is the most essential element of transitional dressing, and you can get creative with it! Cardigans, lightweight sweaters, and jackets (cropped trench coat, blazer, denim jacket tweed jacket) are great options for keeping warm on a brisk evening when it’s not yet chilly enough for a proper cold weather outfit. Try starting with a lightweight summer pieces. Like a tank top, tee, or sleeveless summer dress, then add an extra layer over top for evening.

Swap Your Shoes

There’s no need to pack away your flat sandals until it’s absolutely necessary. But adding closed toe shoes to your rotation like loafers, sneakers, ballet flats, and ankle boots will give your outfit a fall feel and keep your feet warm on chilly days.

Opt for Deeper Hues

One of my favorite ways to capture the essence of the transitioning season is with a color palette that hints at early fall. Beige, tan, muted greens, burgundies, rusts, browns, and more capture it perfectly. These days, retailers typically release a pre-fall collection that includes pieces in fall colors that can be worn now. Like short-sleeve sweaters, lightweight skirts, and dark floral blouses. Incorporating a few of these tones, even if it’s just by way of your accessories, will help your outfit feel a little more autumnal.

Mix and Match Seasonal Pieces

This is my favorite tip because it requires some experimenting. And there’s really no right or wrong way to do it. Combining summer and fall pieces into a single outfit can be as simple as pairing your favorite long sleeve dress with ankle boots. Or, think in terms of top and bottom, like styling fall denim with a tank top or your favorite summer shorts with a lightweight knit.

Experiment with Textures

Cozy textures like velvet, faux fur, suede, corduroy, and leather scream fall, and you can hint at the season with these while also adding depth and interest to your transitional looks. Since we live in a warm climate, I do this mostly by way of accessories and shoes (suede bags and leather flats), but tossing a textural knit over your shoulders can take and outfit from purely summer to summer to fall in an instant.

Summer to Fall Transition Outfits

Since this can be such a tricky time to get dressed, below are 10 summer to fall outfits for different occasions. To shop, click the widgets beneath the image. You can also click the image to shop both exact items and similar pieces to recreate the look in LTK.

Errands

Errands summer to fall outfit

Trench coat outfits are to fall what white jean jacket outfits are to spring. Traditional knee-length trenches are always a staple, but I love this chic take on a cropped swing trench with sneakers and a cap for comfort.

Shower or Brunch

Shower or Brunch outfit

Fall is one of the times of year when I get a lot of requests for bridal and baby shower outfit ideas, and I think this one strikes a nice balance between dressy and casual that make it re-wearable for brunch or even a date. Every great outfit starts with the right bottom, and the print in this Veronica Beard skirt incorporates so many beautiful fall tones, from marigold to olive, berry, and cream.

Game Day

Game Day outfit

Is it really about the football or about wearing something cute to the game? A mini dress like this works well to keep cool during the sunny tailgating hours but should have enough heft to keep you warm as it cools into the evening. I love the touch of fall provided by the western booties and the convenient cell phone crossbody!

Office

What To Wear Between Summer and Fall

When I worked in an office, my favorite outfits would allow me to get ready quickly without sacrificing an elegant, professional finish. This slip skirt adds the perfect autumnal touch in early autumn, and the pops of black lean even more into the darker palette of early fall.

Dinner with Friends

Dinner with Friends fall outfit

I’m naturally drawn to cozy knits in rich autumn hues as it cools off, and the mini length and sleeves on this striped dress make it the perfect transitional piece for a dinner out. Break out the knee high boots for the first time and throw the cardigan over your shoulders to “sandwich” the chocolate browns against the stripes. So chic!

Date Night

Date Night summer to fall outfit

The perfect date night combination for when it’s still warm out but you want a fall feel, a mini skirt in an autumnal print and a moody black sleeveless top is an easy way to keep cool on a warm September evening. These pumps are an Amazon find, and the bag is a Bottega Veneta dupe from Anthropologie.

Special Event

Special event outfit idea

September special events, like weddings, can be tricky, because the weather hasn’t quite shifted to autumn in most areas but the heart is craving sweater weather. I love the idea of satisfying it with a fall-toned dress in a length that’s comfortable to beat the heat. Layer a shawl for evening in case it cools off.

Coffee Date

What To Wear Between Summer and Fall

One of my favorite summer to fall transition outfits for a day that’s looking warm at noon at chilly as the sun goes down is a reliable pair of jeans, a tank top, fall shoes, and a sweater. This is such a practical look to beat the heat during the day, then simply throw the sweater on (properly or over your shoulders) as the temps cool.

Lunch

What To Wear Between Summer and Fall

Similar in concept to the above but a little more casual, this lunch look leans into the sneaker and relaxed denim trends but keeps things from looking frumpy with a tailored top and chic tote. The coatigan shown is one of my favorites of all time by MANGO—it teeters perfectly between cozy and chic and works for both casual outfits and lounging at home. Be sure to size down!

Farmer’s Market

Farmer's Market fall outfit

For the Farmer’s Market or a weekend coffee run, mixing in fall colors in pieces that work for warm weather is the perfect way to start the day. Varley makes comfortable, practical sets and layers, and the belt bag allows for a hands-free morning to pick up coffee, flowers, or groceries from wherever the day takes you.

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