How to Wear Shorts in the Fall

How to Wear Shorts in the Fall

Ah, the age-old problem—when do you put your summer clothes away? And what if you love those summer clothes and want to linger just a bit longer with some of your favorites? Especially if you live in the Midwest (where Lands’ End is based), the weather can turn quickly. You will want to stay warm but also take advantage of those last glorious days of sunshine and summer weather regardless of what the calendar says.

Don’t worry; we have all the solutions you need. Don’t give up those women’s shorts just yet because it’s past Labor Day. You have options. And they are fun and fashionable ones!

Warm Them Up

If there is a chance of a chill in the air, don’t be caught off guard. Whether you need petite sweatshirts, tall, or plus size, we’ve got you covered. Grab a sweatshirt or hoodie to change your summer shorts into an instant casual fall outfit. Traveling? You’ll be ready for a weekend getaway, whether your plans include walking on those cool mornings, sipping coffee outside, or going sleeveless and basking in the afternoon sun.

For even more options, consider adding a pair of tights to your shorts. They will keep you warm and stylish, too. Just make sure to try them out in advance. Some tights are too thick to work with some styles of shorts and still fit comfortably. Neutral colors like black or cream are good, but a carefully curated color can work, too, especially if they match another color in your outfit.

And don’t forget the women’s fleece jackets! We aren’t famous for our fleece jackets by accident. They make a cozy and versatile addition to almost any fall outfit, and you can always toss one into your car or tote bag just in case. Never head out the door to a fall sporting event without one.

A jean jacket can be a great way to warm up those summer shorts, too. You’ll probably want to stick with a classic denim color instead of a white or cream for fall, but remember, most of life does not have a strict dress code—wear what you want and what makes you feel confident and comfortable in your own skin. You’d be surprised what you can repurpose from a cool summer evening into a crisp autumn day while staying stylish.

Dress Them Up

Shorts are one of the most versatile wardrobe pieces you have. For a new fall look, add a crisp blazer to those shorts with a neat blouse or white T-shirt. You’ll usually want to start with a mid to long length in the shorts for this and stick with chinos or other non-denim fabrics that have a little “bulk.” Neutrals are a classic look, but a bright fall blazer can make a statement, and if it is red or green, it can take you right into the holidays. Finish all of this off with your favorite pair of penny loafers or docksiders for a classic look.

The right sweater can also dress up those shorts. Perhaps a lovely soft and slouchy number in a pretty color or a gorgeous white. Women’s cardigans are also natural. The right cardigan can take almost any outfit from casual to crisp. And don’t forget cashmere as an option! A long cashmere cardigan is an instant upgrade in both style and comfort.

Change Them Up

Shorts can also be a springboard to a whole new look. Put those summer sandals and flip-flops away, and add a pair of booties or even knee-high boots for a bold statement. Shorts with tights and booties are both naturals for fall. Experiment with sweaters, too. A long sweater over shorts can be striking, and matching a sweater to your tights can make an instant ensemble.

One of the best parts about changing up your summer shorts is that every single piece you put with them can be mixed and matched with other outfits. If you crave the simplicity of a capsule wardrobe or feel a little boxed in by picking “outfits” for each day, take some time to play with your wardrobe. Pull out your summer and fall clothes, lay them all out on your bed, and see what the possibilities are. Some pieces you will want to keep, others perhaps give away, and this will give you a clear idea of what new pieces you will want to add for this season. And the best part is that all those pants, shorts, tops, sweaters, cardigans, and jackets can be combined in lots of different ways. You can wear all your favorites while still enjoying the variety. Unleash your inner fashionista. Clothes are supposed to be fun!


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