How to Wear Shorts Into Fall

This post may contain affiliate links. Read our entire disclaimer here.

How to Wear Shorts Into Fall

Shop The Look: 7 For All Mankind Shorts (size down) | Theory Tank (M) | BP Cardigan (size down two sizes) | Franco Sarto Bootie (size down a full size) | Prada Crossbody | Blake Kuwahara Sunglasses | Missoma Necklaces Here & Here

I have a new love affair with shorts. Especially now with wardrobes being more relaxed and menopause has kicked in. Voila! Shorts to the rescue. I also like their extreme versatility. Depending on the style, I can dress them up or grunge them down. Yet, as we venture into the fall season, shorts are fun to mix and match with sweaters, cardigans, and jackets paired with booties for slightly crisper, cooler days. I always love extending my wardrobe across seasons, and I am looking forward to wearing shorts long into fall.

I have never really worn shorts that much my entire life. Even as a teenager and twenties, they were not my jam. I have always had insecurities about my legs. My legs are very short (all of my height is in my torso), and I like my thighs even less. The length of most shorts seems to hit at the widest part of my thigh, highlighting the area where I was the most self-conscious. Plus, I am pale, like optic white pale. I could hide in front of a white wall in the winter, and you would not see me. Then, as I got older, I wanted to conceal my varicose veins and spider veins popping up all over my legs. Lately, my knees started to sag. I mean, what the hell!

But then a few things shifted, mainly my mindset. I finally realized that all of the insecurities I had concerning my legs were in my head. The average height for an adult female is 5’-4”. I am 5’-4.5”, so I am actually considered taller than the norm. LOL! Thanks to my Hilliard Studio Method classes, my outer and inner thighs have shrunk. It took time, but their classes diminished my thunder thighs, and changed my entire body for the better. Pale is in, and if you wanted a healthy bronze, we now have sunless tanners that look pretty natural. My favorite is St. Tropez (here you get two for practically the price of one). I use dark on my legs and classic everywhere else.

And let us face it, sometimes wearing shorts is just the appropriate item required for an occasion. Another thing is that I am old. On my next birthday, I turn 52. I am relatively healthy, so who cares if I have pale, veiny, and sagging skin? My husband thinks that I am beautiful. Honestly, that is all that matters. So I put on my big girl panties (not really, I wear a thong like everyone else) and bought shorts.

My Fall Shorts Outfit

I love these 7 For All Mankind shorts (pictured above). They have so much stretch. Typically I would wear a 28 or 29, yet these are a 27 (so order down a size, or order your standard size if you prefer them a little baggy to wear lower on your waist). I can literally pull the fabric out by several inches, and it perfectly snaps back into place.

I ordered this Theory tank both in dark grey and ivory, both in Medium. In retrospect, I should have ordered my usual size small. But I love layering unique tanks over shirts and dresses, so I wanted there to be enough wiggle room. Because of the knit, it would have easily stretched over any garment. I suggest ordering your standard size. A bonus, these tanks are now 75% off. Do not wait, as they will not last long.

I just ordered this BP open front cardigan during the Nordstrom Anniversary sale, both in Rust Leather and Beige Oatmeal. You will most likely see these two colors featured often going forward. They have quickly become my new BFFs.

I will be wearing these Franco Sarto booties in taupe snake print leather year-round because of the neutral color. The heel height makes it flexible for many outfits, from shorts to skirts, dresses, and denim. They are a beautiful bootie that I will enjoy pairing throughout this season. I should have exchanged these for a smaller full size when I received my online order. But honestly, I wanted to wear them that day, so I kept them. I had to put Dr. Scholl’s double inserts in the sole and wear ankle socks to fit. Yet, to be honest, they are super comfortable in how I have adapted them to fit my feet.

This is my go-to Prada purse. I have had it for almost a decade. It accompanies me on every vacation because it surprisingly holds a lot. Yet, it is very lightweight because of the nylon construction. It is easy, casual, and comfortable to use during the day. I do not know why Prada has not made it in other colors than basic black and interchangeable straps. It would sell. You heard it here first.

My Blake Kuwahara sunglasses are prescription, yet most people just buy the frames. Actually, all the sunglasses you see me wearing are prescription. I only go to Sally’s Optical Secrets in Charlotte. She and her staff are always ahead of the trend when it comes to eyewear and sunglasses. I would not trust my fashion glasses to anyone else.

I am currently obsessed with Missoma jewelry. I literally wear them every day. I admire how the pieces are easily layered. If my husband is reading this, you can not go wrong with picking anything from their site. Hint, hint! I will even make it easy and link it for you. LOL!!!

Shopping Tips for Your New Shorts

Let us face it, sometimes we need a lower price to fit within our budget; other times, an item prompts us to splurge. So, I typically showcase multiple options of a similar style or product at different price points. Either the prices list from least to luxe within a collection of comparable items, or I will show at least two price options of a similar style within an overall category. Either way, I try to cover a broader price spectrum depending on your needs.

When you hover over an item below, you will see the retailer, brand, price, and potential sale price. You can even opt-in for sale alerts. Just click ‘♡ Get Sale Alert.’ You will be notified each time the price drops. It is like having your hubby surprise you with the gold aegis chain necklace and the gold snake clip-on pendant from Missoma just out of the blue. That is what a ‘♡ Get Sale Alert’ feels like!

How to Wear Shorts Into Fall

Why is it that we will wear a dress or skirt year-round, but shorts are limited to only a few summer months? All three characteristically show off about the same amount of leg, depending on the style and length. Yet, for some reason, we stow away every pair of cargo, paperbag, and cut-off shorts as soon as Labor Day rolls around. Not this year! With so many perfect fall outfits built around shorts of all lengths, we are guaranteed to look cool but stay warm in these shorts. Lucky for us, most shorts are going on sale as fall clothing is hitting the shelves. So now is the perfect time to nab a pair of shorts (or two, or three!)

Classic Look

You’re Camouflaged

A Wild Ride

A Stroll in the Park

To Work & Back

Fall Shorts Summary

So the tip in how to wear shorts into fall is to focus from your waist up with layering elements. Whether you layer with vests, cardigans, or jackets, this will help keep you warm and appearing weather appropriate. Footwear is wide open, depending on where you live, yet booties are always the right choice with fall shorts. And do not forget a hat to top off your fall outfit.

I am here to answer any questions or help pick out anything you need to transition your clothes into fall or add some new fall favorites. I also curate unique looks and gifts based on your needs, personality, occasion, and budget.

There is also a SEARCH function at the top right of every Golden Tribe page. It helps find whatever you are searching for — answers, tips, products, specific topics, or items. If you can’t find what you are looking for, reach out to me as maybe it is a topic that needs its own post inspired by you!

Stay Golden ~Holly

Shop The Look

>