Casual spring outfits with leggings photo

what to wear with jeggings

By Tina Boomerina (Christina Gregoire)

Teens know how to wear leggings, but adult women over 40, 50 or 60 have stricter fashion rules than teens do. And, I'll tell you all about what to wear with leggings so that you'll look trendy... but not silly.

Read about wearing leggings if you’re over 40 50 60

Can You Wear Leggings When You’re Over 40?

Leggings are still a big hit, no matter what fashion designers and style magazines say (or fail to say).

I was in Paris last summer and I saw women of all ages wearing leggings under miniskirts. And, in the states, where everyone is extremely casual... almost embarrasingly casual... leggings are perfect.

Can You Wear Leggings as Pants?

Yes. You will love wearing leggings as pants, as long as you wear them the right way.

Leggings are a great style for apple shapes, because leggings and jeggings are stretchy. So, leggings will fit you... even on days when nothing else does.

And, most of us will become apple shapes eventually due to the natural decrease in estrogen... something which happens to us as we get older.

Actually, I have been an apple shape all of my life, so I know quite a bit about wearing leggings without looking absurd or embarrassing... well... I'm good with leggings most of the time.

Tunic Tops Over Leggings

If you are over 18 and you don’t live in the Playboy Mansion, you must wear your leggings with a top or tee that's long enough to cover your hoo-ha and your booty. No exceptions, ladies.

What to wear with leggings:

  • Long tunics: Your tunic tops should reach mid-thigh... if you plan on sitting down.
  • Flirty dresses and skirts: Wear your leggings as tights.
  • Big shirts: Your top must be long enough to fulfill the requirements.
  • Big shirts with belts: See above.
  • Long, roomy sweaters: Ditto.
  • Long, T-shirt tunic dresses: This may become your go-to casual look.

NOT Clothes to Wear With Leggings

The legging trend uses the silhouette of big over narrow. (Big top, narrow legs.) If you are wearing your leggings as pants, you cannot wear them with:

  • Any short top.
  • Any tight-fitting top.
  • I don't flipping care what J-Lo wears... No excuses. If I catch you, I'll send you to the back of the line.

How to Wear Jeggings Over 40, 50, 60

You will love jeggings.

If you are over 40, you will love wearing jeggings instead of jeans. Jeggings are like denim tights or very skinny jeans. And, any apple-shaped woman (of any age) who has had children will find that jeggings are more comfortable than jeans.

When you hit 40 or 50, you will notice that most jeans suck... and jeggings are a chic alternative to the dreaded “mom jeans”.

(Update: As soon as I tell women not to wear something, it seems like it becomes hip with young chicks in London. Please ignore the new "mom" jeans. It's not hip to wear the mom-jean trend if you actually are a mom. It's just embarrassing... and no one will think you're cool... which is the whole reason for wearing something like that.)

Read how to wear leggings if you’re older

How to Wear Leggings for Older Women

Apple Shaped Women

In fall and winter, apple shapes should take advantage of their shapely legs by wearing their leggings under a long T-shirt or T-shirt dress and covering the whole outfit with a sweater coat or belted trench coat.

If your trench is cute enough, you can wear that same outfit anywhere, from the malls of North America to the streets of Paris. However, you must wear leggings (or jeggings) that are heavy enough not to be confused with tights.

Read about leggings for women over 40 50 60

How to Wear Leggings When You’re Over 50


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Cropped Leggings... How Long Should My Leggings Be?

I have found that decent leggings will morph to fit almost any body, but I have a few opinions about legging lengths... for those of you who are not tall enough to be models:

  • Short chicks should go sleek by wearing long leggings that reach their shoes or ankle booties. Women under 5'7" need to create a long, unbroken line of leg.
  • As for cropped leggings, I am not a big fan, personally. I just don't think cropped pants look good on some women... like me. So, when in doubt, go long.
  • You, my dear friend, may be the exception to the rule. I have seen short women who look good in cropped pants, so follow your instincts.

How to wear cropped leggings:

  • With boots: If you already own some cute cropped leggings and you've decided you don't look great in cropped pants, you can wear your short leggings by tucking them into knee boots or over-the-knee boots.
  • With high-heeled boots: Any kind of boot will make your legs look longer, even if you're short. And, if you're seriously vain like me, you should wear boots with a heel.
  • When you're on vacation: Cropped leggings look good at the beach or on a cruise ship, when worn with tennies or flat sandals.

how to wear tightsTall women look hot in mid-calf leggings or in any kind of crops. If you're tall, you will look fabulous in leggings and ballet flats or flat boots or high-heeled boots.  As always, lucky women who are tall have the option of wearing whatever their little hearts desire.

Amendment: If you're short you CAN wear leggings with ballet flats. You just have to be super careful about keeping the proportions of your outfit right. Have someone take a photo. I always learn something when I look at a photo taken by my impatient husband... after I tear up the picture and run screaming into the bedroom... only to find out (3 days later) that he's posted it on facebook.

Rules for Leggings

Even if you wore leggings in the 80s and you think you are Little Miss Knowitall, I will feel better if you sit up straight and pay attention to these reminders:

  • You are neither Cher nor Lady Gaga.
  • You are not Olivia Newton John in Grease.
  • You must not wear shiny leopard or neon pink leggings. (This is for your own good and you will thank me later.)
  • Leggings are not really pants; they are a layer.
  • Leggings must be thick enough that your waitress cannot guess what color underwear you are wearing (or not wearing).
  • Most short women should match (or blend) their leggings to their footwear.

What Shoes Should You Wear With Leggings?

Leggings are fabulous with ballet flats, flat ankle boots, low-heeled boots, and high-heeled boots with “sturdy” heels that could never be referred to as hooker boots, even if they reach the thigh.

If you are wearing your leggings more like tights than like pants, for example, wearing leggings under a dress or skirt, you can wear any type of boot or shoe. That includes stilettos... if you must. And, that includes over-the-knee boots, ankle boots, and fold-down (cuffed) boots.

When in doubt:

  • Ask your daughter. She will tell you the truth.
  • Consult your full-length mirror and ask yourself if you look like you just came from Wallymart.
How to wear leggings over 40 50 60 - article

Good Tops for Leggings Outfits

In most circumstances, there is no upper age limit for wearing leggings or jeggings. If you do them right, leggings and jeggings will look like trousers and jeans. However, if you start laughing when you look in the mirror, change into something else.

Leggings are comfortable and warm. As long as you follow the rules, and you rely upon your excellent taste, you will always know how and where to wear leggings.

More Articles for Baby Boomer Women:

Photo Credits:

  • Main Photo: House of  Fraser.
  • Can You Wear Leggings When You're Over 40: Simply Be.
  • How to Wear Leggings for Older Women: Simply Be.
  • How to Wear Leggings When You're Over 50: Maryling, Debenham, LaRedoute, Asos.
  • Cover Your Butt: Fifty Plus.
  • Good Tops for Leggings Outfits: Edinburgh Woollen Mill, LaRedoute.

What do you think of this article? Leave a comment at the bottom of the page or give us a Google Plus or follow me on Pinterest at Tina Boomerina - Baby Boomer Chick.

(And, if there are any photos missing, some pics decided to take a leave of absense when we updated the site. You can ask me, but there's a good chance the older clothing is no longer around.)

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