BASICS

Feel Your MOST Confident Wearing Shorts Over 40 With These 8 Simple Style Tips

How To Wear Shorts Over 40

We’re talking about one of the most controversial fashion items for women over 40…shorts! I get tons of questions around this time of year about how to wear shorts over 40, what shorts are best for women over 40, how to style shorts…the list goes on and on. There may be voices in your head saying you can’t wear those shorts. But there’s another voice saying…IT’S HOT, I want to wear shorts, and I want to look good doing it! But how?! Don’t worry, if you’re wondering how to style your shorts this summer while still looking chic and sophisticated, this post has all of my best tips! Plus, I’m sharing some of my new favorite shorts for the summer…

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, ted baker d-ring belted shorts, ba&sh floral blouse, rag & bone straw hat, sam edelman sandals

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, ted baker d-ring belted shorts, ba&sh floral blouse, rag & bone straw hat, sam edelman sandals

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, ted baker d-ring belted shorts, ba&sh floral blouse, rag & bone straw hat, sam edelman sandals

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, ted baker d-ring belted shorts, ba&sh floral blouse, rag & bone straw hat, sam edelman sandals

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, ted baker d-ring belted shorts, ba&sh floral blouse, rag & bone straw hat, sam edelman sandals

SHORTS | BLOUSE | HAT | FOR LESS | SIMILAR SANDALS

Tip #1) Try A Longer Inseam

If we’re trying to look sophisticated, we don’t want to wear tiny short shorts like our teenage daughters, right?! So, when you’re shorts shopping, look for a longer inseam! Between a 4–5-inch inseam length is ideal. But if you’re petite (under 5’4”), you can get away with a 3–5-inch inseam length. Another fool-proof way to check the length of your shorts is the fingertip test. Hold your arms by your sides and if your fingertips are at or below the bottom of the shorts, that’s a good length. Another popular option is Bermuda shorts. But they can be tricky because they can cut you off and make you look shorter. Look for a pair of Bermuda shorts with a 7-9-inch inseam and make sure you style them in a chic way. A lightweight, longline blazer can look very chic and stylish with any pair of shorts, but especially cool with Bermuda shorts.

Another major tip for styling your shorts is to make sure you pair them with a top that’s more refined and elevated. The problem with wearing shorts is that they can sometimes look too casual. So, elevating the look with those more interesting, chic pieces can help. Instead of a plain tee, opt for a tee with an interesting design detail like puff sleeves, ruching, ruffles, a print, or a strategically placed cutout.

The little details are what make the biggest impact.

 

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, brown jonathan simkhai vegan leather shirts, white rails cotton button down shirt, veronica beard woven sandals, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, brown jonathan simkhai vegan leather shirts, white rails cotton button down shirt, veronica beard woven sandals, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, brown jonathan simkhai vegan leather shirts, white rails cotton button down shirt, veronica beard woven sandals, saint laurent sunglasses how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, brown jonathan simkhai vegan leather shirts, white rails cotton button down shirt, veronica beard woven sandals, saint laurent sunglasses
how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, brown jonathan simkhai vegan leather shirts, white rails cotton button down shirt, veronica beard woven sandals, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, brown jonathan simkhai vegan leather shirts, white rails cotton button down shirt, veronica beard woven sandals, saint laurent sunglasses

SHORTS | TOP | WEDGES | NECKLACE

Tip #2) Try Shorts with A Wider Leg

Avoid shorts that are super tight. Instead go for shorts that have a wider leg. The tighter the shorts are around the leg, the bigger your legs will look. If you give yourself some room in the leg, your legs will actually look smaller. Look for a pair of flare or A-line silhouette shorts. The Jonathan Simkhai shorts I’m wearing above are the perfect example. You can see the wider, A-line silhouette actually makes my legs look slimmer and longer. The A-line shape can also help mask or minimize your hips, butt, and thighs if that’s your problem area. I styled the shorts with my favorite Rails button down and a new pair of woven wedge sandals by Veronica Beard that are perfect for summer.

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, red alice + olivia shorts, red alice + olivia denny blazer, malone souliers pumps, express cami

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, red alice + olivia shorts, red alice + olivia denny blazer, malone souliers pumps, express cami

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, red alice + olivia shorts, red alice + olivia denny blazer, malone souliers pumps, express cami how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, red alice + olivia shorts, red alice + olivia denny blazer, malone souliers pumps, express cami

SHORTS | BLAZER (SOLD OUT) | SIMILAR CAMI | SIMILAR HEELS

Tip #3) Buy High-Rise

Choosing a higher rise will make your legs look longer. This is true for all bottoms…pants, jeans, skirts, etc. But a higher rise also helps create a waist. If you really want to accentuate the waist, wear something like the Alice + Olivia set I’m wearing above. The cropped tank hits right at the top of the shorts, which helps show off the waistline, and the blazer slims the sides even more. You could also add a belt to help create waist definition. So what rise is best?? The ideal rise for everyone is different. Generally, anything above 9 inches is considered high rise, but I’d look for something in the 10-inch zone.

By the way, I know shorts shopping can be really tricky. My go-to brands to look at when I’m shopping for shorts are Alice + Olivia, A.L.C., Ulla Johnson, Frame, Marissa Webb, and Amanda Uprichard. J. Crew is also very clear on rise and inseam length and has a lot of options.

If you’re looking specifically for denim shorts, make sure you check out this post!

 

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, green ted baker d-ring belted pants, white rails cotton button down shirt, marc fisher gold chain sandals, chloe sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, green ted baker d-ring belted pants, white rails cotton button down shirt, marc fisher gold chain sandals, chloe sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, green ted baker d-ring belted pants, white rails cotton button down shirt, marc fisher gold chain sandals, chloe sunglasses

SHORTS | TOP | SANDALS (SOLD OUT IN BROWN) | SIMILAR IN BROWN

Tip #4) Size Up

Do NOT get caught up in the vanity sizing. Just because you’ve been a size 6, does not mean you’re going to be a size 6 in every piece of clothing and every pair of shorts you try on. I’ve been ordering larger sizes in my tops, jeans, and shorts lately because right now, I’m really just enjoying a roomier fit. I even ordered my favorite Rails top (above) in a medium for a more oversized fit! Sizing up in your shorts gives you a little extra wiggle room and will actually make them look more flattering on your stomach and legs, polished, and elegant.

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, marissa webb pinstripe shorts, white see by chloe pleat sleeve top, see by chloe platform heels, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, marissa webb pinstripe shorts, white see by chloe pleat sleeve top, see by chloe platform heels, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, marissa webb pinstripe shorts, white see by chloe pleat sleeve top, see by chloe platform heels, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, marissa webb pinstripe shorts, white see by chloe pleat sleeve top, see by chloe platform heels, saint laurent sunglasses

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, malibu, california, marissa webb pinstripe shorts, white see by chloe pleat sleeve top, see by chloe platform heels, saint laurent sunglasses

SHORTS | SIMILAR TOP | HEELS | NECKLACE | SUNGLASSES

Tip #5) Choose Shoes Strategically

Since you’re showing a lot of leg, your shoes are really important. I would go with a pair of sandals or heels that match your skin tone. It doesn’t have to be perfect, but in the general zone. Another tip: If you add heels or wedges, it gives you more height! I’m wearing these cool pinstripe Marissa Webb shorts with a pleat sleeve tee by See by Chloe. The tee is sold out but I linked a more affordable option I own and love. On my feet, I went with some tan See by Chloe platform heels. You can see that the color doesn’t perfectly match my skin tone, but it’s in the same zone and therefore helps elongate my legs.

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, black nation LTD long sleeve t-shirt, moussy vintage denim shorts, valentino reversible belt, bottega veneta chain cassette bag

SHORTS | FOR LESS | TEE | BELT | BAG | SIMILAR SANDALS

Tip #6) One Skin Rule

I’ve talked about the One Skin Rule many times. And I know that during the summer, it’s tempting to throw on a tank top with your favorite shorts. But since you’re showing so much skin on your legs, it’s best to wear a top with short, 3/4, or long sleeves. I did live in Texas for 8 years so I know how hot it can get. But wearing longer sleeves in natural, breathable fabrics (like cotton or linen) will still keep you cool and looking sophisticated and elegant. Also, don’t forget those elevated style details I mentioned earlier…puff sleeves, ruching, wrap front, texture, etc. My secret weapon when it comes to cool t-shirts is the brand Nation LTD…the fit is great, the fabric is high quality, and they are what I like to call t-shirts in disguise because they look like blouses and can really elevate a look!

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, white paperbag shorts, vince camuto green woven heels, cinq a sept mint green blazer, express cami

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, white paperbag shorts, vince camuto green woven heels, cinq a sept mint green blazer, express cami

SIMILAR SHORTS | ANOTHER OPTION | BLAZER | SIMILAR CAMI | HEELS | NECKLACE

Tip #7) Body Care

Last but certainly not least…take care of your legs! If you’re going to get them out, make sure you shine them up! What I like to do is take some lotion and mix it with this Charlotte Tilbury Super Model Glow and rub that into my legs. If you are going the tanning route, make sure you proceed with caution so that you don’t end up staining any of your clothes, sheets, etc. We did an entire post on self-tanners for summer here if you’re interested. Adding the color just makes my legs look a little better and makes me feel good! You’ll walk out the door feeling a little more confident. Another thing that will help make your legs look darker is adding a pop of color. In the look above, I’m wearing a pair of super flattering paper bag shorts with a simple cami and one of my favorite blazers by Cinq a Sept. I love the pop of color and this mint green is perfect for summer!

how to wear shorts over 40, best shorts for women over 40, how to wear shorts over 50, flattering shorts for women over 40, best shorts for 40 year old woman, best denim shorts over 40, too old to wear shorts, how to find the perfect shorts, what to wear with shorts, erin busbee, busbee style, telluride, colorado, white paperbag shorts, vince camuto green woven heels, cinq a sept mint green blazer, express cami

Tip #8) Tie the Look Together

Now you have the perfect pair of shorts, a chic elevated top, strategically selected shoes, and summer-ready legs…what else do you need?? To kick your shorts outfit up a notch, make sure you complete the look with accessories that can pull it all together. It could be a hat, belt, cool pair of shoes, chic sunglasses, or some statement jewelry. I’m wearing a cool, chunky gold necklace with the look above and it just adds a little extra oomph!

For more of the do’s and don’ts of wearing shorts over 40, make sure you watch this video. And to see more women over 40 wearing shorts, this post is a must-read!

What other questions do you have about wearing shorts? We’re happy to answer them! Please leave a comment below.

To get blog posts delivered directly to your inbox, along with some incredible resources, be sure to sign up for the newsletter here.

How To Manifest Anything, Fashion blogger Erin Busbee of Busbee Style wearing an orange and blue Staud Ina dress with white sunglasses walking around in Telluride, Colorado
Erin Busbee
After a decade in TV news, a desire to help women "look pretty" sparked a career pivot. I started my own wardrobe consulting business, styling "real" women for many years. In 2014, I changed direction again, using my TV background and styling expertise to launch this website and my YouTube channel. We are now a community of well over 1 million dynamic, vibrant, amazing women over 40... who know that age isn't something you need to hide from. For us, life is just getting started!!
Join the Conversation
Leave a Reply to Mary C Cancel reply

4 thoughts on “Feel Your MOST Confident Wearing Shorts Over 40 With These 8 Simple Style Tips

  1. I’m 65 and no longer have nice legs. They are heavy and quite unattractive, so I will wear longer knit shorts around the house on a hot day, but switch to a knee-length dress or skirt for going out in public. It’a a much better option for me and better for my self-esteem as well. I’m glad there are so many cute summer dresses!

  2. I am a petite woman in my 70s and I am in very good shape. I live in Westchester, so there are a number of high-end stores where I shop. After looking at the shorts you say are fine for older women, I totally disagree with the length. I feel that they are much too short for a senior woman, and would not flatter women with legs that might not be that thin. I think the short should end mid to a little above thigh length (anything shorter looks like the woman is trying too hard to look young).
    I definitely believe that senior women can wear shorts, but in a more sophisticated look (not styles that are more suited for younger women).

    1. Wow! Good for you for staying in such great shape. I think we are saying the same thing… inseam length and style of shorts are key. Confidence and contort are also very important. Thanks for your note. Erin xo

Explore More

Posts You'll Love
STYLE

No Joke! These Sneaky Outfits Feels Like You’re Wearing Pajamas

Find out exactly what you need for the perfect loungewear outfit you can wear from…
Read Post
Shop
BASICS

5 Chic Ways to Wear a White Blazer This Summer

These are the outfit ideas you need for styling your white blazer this summer!
Read + Shop
BEAUTY

The 7 Best Mascaras for a Smudge-Proof Summer!

Rising temperatures mean it's time to switch up your beauty products. We’ve got 7 of…
Read Post
Shop
Mind

6 Strategies for Coping with Stress in 20 Minutes or Less

As a busy, working mom, you need stress relievers that are quick and that work.…
Read + Shop