How to Wear Leggings

June 15th, 2009

How do you wear leggings?  Glad you asked.  We’ve created three outfits for your inspiration pleasure as a case study for how to wear leggings:

Outfit 1: Leggings + Casual Blouse + Miniskirt + Flats

How to Wear Leggings

Feeling the love for this outfit?  Here’s more information about it.


Why does this outfit work?  It’s a study in monochromatic dressing—perfect for those of you who are hesitant about trying leggings out.  The grey blouse pairs well with the grey miniskirt—and the grey leggings.  This kind of monochromatic dressing is great for petites, as it creates an unbroken vertical line, making you look taller.  Visual interest is added to the outfit with a pair of royal blue flats and a structured handbag to match. 

Outfit 2: Leggings + Tunic + Jacket + Boots

How to Wear Leggings


Feeling the love for this outfit?  Here’s more information about it.

One of the easiest ways to wear leggings is to pair them with a tunic.  We chose a tunic in bright blue to add a visual punch.  Paired with the bright blue tunic is a pair of leggings in a darker blue color, to create a unified look.  We added a short sleeved jacket to layer over the tunic—with a bonus shot of style in the form of a checkerboard plaid pattern.  We finished off the outfit with a pair of ankle boots for a sleek, sophisticated look.

Outfit 3: Leggings + Casual Dress + Pumps

How to Wear Leggings

Feeling the love for this outfit?  Here’s more information about it.


Wearing a dress over leggings is a popular way to layer.  We have two dress recommendations for pairing over leggings: (1) a close fitting dress (such as a knit dress), cinched with a wide belt, or (2) a billowy bohemian style casual dress.  Whether you go with the close fitting or the more loose fitting dress, choose one that falls at or above the knee for the most flattering silhouette and best effect.  P.S. Don’t you love that clutch handbag?  It instantly dresses up the knit dress.

We’ll leave you with five last thoughts on how to wear leggings:

(1) When you wear a shirt over leggings, your shirt shouldn’t fall past the middle of your thigh.  Any lower will throw off your proportions.

(2) When you wear a dress over leggings, the rule is that your dress should fall at or above your knee.  If your dress falls below your knee, you run the risk of visually cutting off your legs.  Not very flattering.

(3) The key to wearing leggings in style is to get the big-over-small silhouette.  So when you choose a shirt to pair with your leggings, look for a roomy shirt that’s anything but skintight.  Skintight top + skintight leggings = Minus points for style.

(4) When you look for shoes to pair with your leggings, look for three styles: flats, boots, and pumps.  Other types of shoes tend not to work as well as these three styles.  Our personal favorite is booties with leggings for a rocker chick inspired look.

(5) Our last tip will help you choose a color for your leggings.  When choosing a color for your leggings, we recommend echoing another color already existing in your outfit.  That is, if you already have grey in your outfit, a grey pair of leggings could be a great choice.  But if you don’t already have red in your outfit, don’t try to slip on a pair of red leggings.  Or do it knowing that it’s either going to be either fabulous or frightening…nothing in between.

Have a great tip about how to wear leggings? Share it with us in the comments!

Entry Filed under: How To, Ready Made Outfits, Women, Women's

18 Comments Add your own

  • 1. Sal  |  June 16th, 2009 at 7:14 am

    Next time someone asks for legging-wearing advice, I’m sending them RIGHT HERE.

    My only additional tip is to beware of cropped leggings. Unless you’ve got very slender calves, they can be quite unflattering.

  • 2. Allison  |  June 16th, 2009 at 8:10 pm

    Is there a guide to different types of sunglasses on this website? Thanks.

  • 3. Melinda  |  June 17th, 2009 at 6:28 pm

    Do you have any advice on where to get really great leggings? There are so many kinds out there that have the unpleasant shine to them when they stretch, even if they’re the right size.

  • 4. Esther  |  June 18th, 2009 at 11:14 am

    But are leggings appropriate for over 40’s? I’m 42 and in great shape (and Korean, if that helps). I also live in NYC.

  • 5. Yanet  |  June 19th, 2009 at 2:45 pm

    I see many girls were leggings with flipflops which does not look good. Very tacky!

  • 6. roni  |  June 21st, 2009 at 10:25 pm

    I have actually never seen leggings look nice, they are not at all flattering for any body type; the colors, fit and lengths are atrocious.. all the outfits you proposed for leggings would look so much better with actual pants or jeans.

  • 7. Cameron  |  July 15th, 2009 at 3:19 pm

    Hi Esther, I work with a lady who is 45 and wears leggings in some way just about everyday and she always looks really cute. Just wear them, and don’t worry about what any naysayers say. your hubby/bf will love them too :)

  • 8. Scoutabout  |  September 3rd, 2009 at 5:56 pm

    Leggings will always be controversial - people either love them or hate them - but they have become a wardrobe classic and are here to stay. They will be subject to trends that come and go, with different patterns, colors, textures and embellishments, but your basic black legging will never go out of style. I’ve also seen leggings on females of all ages, even into their 70’s and older. They look great on everyone, provided they are paired with clothing that works with leggings, your figure and your age. As a 52 year old woman, I avoid brights and pastels and anything too trendy, sticking instead to basic black, navy, brown, gray or muted colors.

  • 9. crystal  |  September 14th, 2009 at 8:05 pm

    I’m a 43 year old women in great shape and I love leggings. I just keep it simple and it works all the time. I usually pair my black leggings with a white button down shirt that hits me mid thigh , a pair of ballerina flats and a large handbag. Awesome!!!!!!!!!!!!!

  • 10. lisa  |  October 26th, 2009 at 7:30 pm

    Great advice, I wore them the first time around in the 80’s and as a woman of 41 i’m going to give it a try again. wonderful pics of outfits.My only advice for us older woman stay away from super short minis and wearing them with tee shirts.Leave this to the younger ones.Stick to dresses and tunics listed above.Older gals should look polished, chic not cute.

  • 11. brianna  |  January 31st, 2010 at 11:25 am

    i have a brown shirt and i would like to know what color leggings to wear with them?

  • 12. crishalyn ruzgal  |  June 23rd, 2010 at 3:27 am

    the dresses are beutiful

  • 13. Anonymous  |  August 14th, 2010 at 11:05 pm

    I think leggings are great! They are cool with a big shirt, which can be belted or not.
    the Big Boy shirt and leggings look great with flat shoes, loafers in silver with a buckle, great looking sandles with a tiger look or just flat colored shoes.

  • 14. Judy  |  September 12th, 2010 at 4:12 pm

    Thanks for the tips…especially for those of us in our 40’s.

  • 15. MARIBELLE S. MAGLANTAY  |  September 21st, 2010 at 9:40 pm

    Is it okay if I’m gonna wear a LEGGINGS+CASUAL BLOUSE+SHORT+FLAT SHOES. My height is only 4′11″

  • 16. RMR  |  March 1st, 2011 at 9:53 am

    I’m 50 and fat and wear leggings all the time with long shirts and keep it extremely simple. Don’t like it? Don’t look! *heh*

  • 17. Ma Petit Chica  |  June 14th, 2011 at 6:18 pm

    My mom never allows me to wear leggings because of my height (4′11). Can petite girls wear leggings?

  • 18. Kristy  |  August 24th, 2011 at 12:58 pm

    @MARIBELLE
    Wear heels then it’ll work out better, and not chop up your body too much!!!

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