Sunday, September 19, 2010

Leggings: to wear them OR not to wear them....

(photos: Ann Taylor Loft)

Dear SYSters,

It’s now officially the beginning of fall (according to the stores). It may not yet seem like fall where you live (I know, it’s over 90 degrees here) but it’s time to start thinking about the new fall fashions—even if you can’t wear them yet.

Preparing your wardrobe ahead of the cooler weather will assure you style will shine all season long. I’m happy to report many stylish SYSters are beginning to put their fall wardrobes together right now. I’m so looking forward to the first cold day I can wear my new gray boots—aren’t you?

So far this season here is the one question I’m asked most often:
“I’m over 40, can I still wear leggings?”

This is not a “one size fits all” type of question to answer. However, that being said, you’re never too old to wear leggings. Really, you are not too old! What is more important is how or what you wear them with!

You should wear leggings with longer tunics, dresses above the knee, sweater dresses and long boyfriend jackets and sweaters. Your bottom should ALWAYS be covered when wearing leggings. Leggings look equally good with flats, pumps or boots/booties (depending upon what you are wearing).

Which color of legging is best? For the best look, select leggings in the same color as the shoe you are wearing. Leave the zebra print leggings and bright colors to the teenage girls!

STYLE TIP: Treat your leggings like tights—don’t wear them like pants. Follow this tip and you’ll never look like you forgot your pants. Instead you'll be “Showing Your Style” SYSter—every time you wear leggings!

Love, Leslie MSP

Ah, NO! Wearing a different color of shoe makes your legs look stumpier! Not a good look....

Ah, NO! Ladies, don't do this...Cover your bits!

Do pair up a longer tunic or sweater (or dresses & skirts) with your leggings....


What's your opinion about leggings? Are you going to wear them with me this season?Join my MSP’s facebook fanpage and give your opinion about leggings and more:


  1. Leslie, what a timely post as I was just thinking of trying to find some leggings for my fall wardrobe! I have further questions though. You said that the leggings should be the same color as your shoe but I'm still not quite sure how to do that. If I wear a brown dress/skirt (that hits above my knee) what color leggings/shoes would I wear with that?

  2. Megan,

    Consider tights instead of leggings. Perhaps a chocolate brown textured tight and matching shoe.

  3. Dear MSP,

    Thank you for all you do. I am an almost 50 FLYbaby that over the summer decided to 'upgrade' her look at work this school year, as a class room aide. I am an hourglass 22W and have been following your style tips. I mostly thrift shop but have bought some new, on sale retail using your tips. I hate trying on at store, but most stores are good about returns with receipt. Anyway, I also subscribed to blog for the daily wear calendar. I love it. I have been brave enough to step out of my neat top/neat jeans look for the last 4 weeks and it makes me feel great to be confident with the other fashionistas! Last Monday, I wore an Old Navy Khaki, Belted Cargo Tunic Shirt dress (G-will,$5.50) Denim Jeggings (Lane Bryant, about $22.00 on sale) Candy sports clogs($5.99 Savers) and a full price turquoise cascade necklace from Torrid (15.00) Using MSP tips like matching shoe color to hair and wearing good foundation garments, I Rocked that outfit. I knew I looked good stepping out the door and I got compliments all day. I NEVER would have worn such form-fitting bottoms under my current size circumstances, carrying 270 lb on a 5'8" frame, before I read you. The last way you helped was 2 days before school began, they announced a new dress code for staff. Luckily I was prepared from my own resolution,but we decided to do a swap so those aides who were jean oriented had new "upgrades" from others that we didn't like for ourselves or that we had "grown" out of. By adding that accessory here or paying more attention to fit and detail, even the jeans wearers are still making the grade (supposed to be wearing slacks now). I have steered a few new fans your way, including prior sweatpants moms! We love you, Ruth

  4. I wear lots of jeggings (the heavier 'jeans' type) with tunics and dresses in the autumn/winter - it's a very popular Danish trend. Keeps you warm too! ;D

  5. Thanks so much for this post. I just turned 43 and I'm terrified I will not dress age appropriate! Part of it is my size. I wear a 2-3 so sometimes I do err on the side of too young because those are the clothes that fit. Thanks to you, I have a better idea of whether something would look okay on me at my age or not. My son's girlfriend says I look young enough to pull of younger looks.
    I was talking about leggings with my husband last night and he said he thought it would look very nice on me. I was still this post today is just what I needed. :D Thanks for all that you do to keep us looking our best no matter our age or shape or size.
    Love ya!

  6. Pammer,

    You are quite welcome!

    I say....Follow the fit guidelines and rock this style!

    {{hugs}} Leslie MSP

  7. Oh I love the look of leggings...but where I am more of a plus sized person (btwn 16-20 depending on the cut, brand, etc), I don't want to look like a train wreck. Oh ya...and I am 5'4", too. I have looked at the leggings and the long tunics...but I just can't do it.

    What are your thoughts? Can all body types wear leggings?

  8. Would you say these same rules apply to skinny jeans and jeggings?

  9. @Amy...instead of the long tunics...I would suggest a sweater dress instead. It's a popular style and you'd look great in it!

    @Marewalker, skinny jeans and jeggings are a bit thicker and more pant like so you could wear a shorter top/sweater if you like.

  10. Last year I wore black leggings under a right-above-the knee black swishy-style skirt. Wore my dark brown to-the-knee boots with it, and a cute cardigan on top. I felt good in it...modern and hip. So I'm thinking I did ok(?) I'm 52.

  11. @Sherri, you did REAL good! Your outfit sounds stylisly "on-trend" would work again this season too (with your brown boots).

    However, another trend you can try is switching out the boots for a platform heeled shoe. This is a popular trend this season--it's just a thought!

    Keep on stylin'SYSter!

  12. I think I'm too thin to wear leggings... like my legs are very thin. I'm 5'4" and 108lbs... 27 today! Anyway, if I don't like looking very thin, would you agree leggings are not for me?

  13. Dee, I'd agree if you feel your legs are too thin, don't wear the leggings (this style will bring attention to your legs)....however, why don't you consider a slim straight-leg pant instead? A slightly wider pant opening would actually be quite flattering and you can wear them w/ all the wide tops, capes, sweaters and ponchos!

  14. I only like the look of leggings under a dress with boots or ballet flats but it's still not a favorite look. And I think it's a very young look that I'm too old for. I just don't like the look of leggings. They're barely a step above people walking around in pajama bottoms, imho.

  15. Judy,

    If you don't like 'em don't do them.

    There are other options like straight legged pants and sheer tights under dresses!

    It's all about your comfort zone and feeling good in what you wear!

  16. I usually buy Hue leggings but those look nice too, so maybe I'll have to give those a try!

  17. I'm 50 and I love wearing leggings with an oversized t-shirt to do housework in, along with my socks and slide-on Birkenstocks (I have foot problems). The hugging effect of the leggings keeps me warmer so that I'm ready to FLY.


Thanks for leaving your comment. I hope you enjoy my blog and stop by often!

Love, Leslie 4 Steps to Chic 4 Steps to Chic by mspsmartypants featuring summer handbags Junya Watanabe black and white striped tee matchesfashio...