How to Wear Leggings


I’ve had a few requests on how to wear leggings after my post the other week.  So here are some ideas if you’re no longer in your twenties or don’t want to show off too much leg.

From left to right:
A skirt that is a bit too short – leggings that go over the knees in a similar colour or slightly darker colour are a great way of distracting from a short length skirt, or a long tunic.  The shorter the skirt, the more opaque the legging needs to be.
An unusual construction dress or skirt if you may be flashing too much leg, try a thick legging as an alternative to a very slim cut trouser.
Dark dresses can be teamed with a matching hose style legging – here is a maternity dress in brown with a brown legging.
Knee-length dress with a hose style 3/4 legging, makes the dress a tad longer and hides and slims your knees and calves, but you can add some detail with a lace or other trimmed hem if you want.
Leggings have a modern look, so keep shoes simple and low vamp and also modern to suit.
Beware of shiny leggings as you age – they draw attention and are more suited to the teens and twenties than 40+.  If you like patterned hose or leggings, be aware they they are drawing attention, be happy for that attention to rest on your legs.


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  • Imogen – the purple top & skirt… would that outfit suit a pear shape (not extreme pear, & fairly slim, but with heavy thighs/calves)? I love the skirt but am nervous about drawing attention downwards (I'm also only 152cm with proportionally short legs). I also love the second outfit – it's gorgeous! Can I ask another leggings question as well – I usually team long leggings with an empire line tunic & boots because 3/4 leggings feels like chopping off my legs & therefore a bad idea. Can a short-legged person wear shorter leggings?

  • i was surfing the whole day,looking for ideas on how to wear my new black leggings….. could have saved me a lot of time,if i just started here….thank you Imogen for this great post!

  • Mel – yes you could wear it as the design of the skirt would hide your thighs, a dark legging (long ones to your ankles) would hide your calves.

    If you want to wear shorter leggings, look for a nude coloured shoe to blend with your legs so you don't break up your legs further with extra horizontal lines.

    e* – thanks so much for stopping by – happy to help!

  • Thank you Imogen! I like the two in the middle. I wonder how come it is just so odd for me to wear leggings? I have no difficulties with capris, ankle length and turned up jeans. I have long,skinny legs and I love opaque tights. Maybe it is just the idea of having to wear shoes without socks! I´m also interested in functionalism- also in dressing, and keep wondering about the functionalism of leggings. Can you help me on this one?

  • Metscan – the functionality for me with leggings is that I can wear a peep toe or non-closed toe or heel shoe, which I wouldn't wear with regular hoisery. Also, I often wear them on days when it starts off cool, but may end up hotter, and I can easily take them off.

    For some, who have varicose veins on their calves, it's a good way of disguising them without the formality of full hoisery.

  • metscan, I too live in a cool climate so often wear footlets inside shoes with leggings. But there comes a time, usually late June or early July in this hemisphere when leggings look too heavy no matter what. IMO a legging should sit either just above the ankle or at the lower part of the calf. If too long, they look like long underwear.

  • Ha, haa Duchesse: You said it; underwear, that´s how they look on me! Great, now I have to curl them up a bit and take another look. Thanks!

  • Imogen I love these outfits! I've long been a fan of leggings. They bring a youthful, quirky touch to an outfit.

  • Sallymandy – thanks! Polyvore is a fun tool to play with.

    Sal – I think the skirt is from Dorothy Perkins (you can click on it to find out), not an expensive brand).

    Duchesse – I definitely wouldn't wear them mid-summer, but they are great option for when it's too chilly.

    Metscan – if you go for the more sheer variety (rather than the very heavy) you will find they look more like hoisery not underwear.

  • Jamtart – thanks! In Melbourne the weather has turned to full on winter suddenly, so I won't be wearing any for a while, instead I'm getting out my boot collection!

  • Loved the low vamp distinction you gave me the other day. . . I know look at all my shoes from that perspective, you are such a genius.

    I have a question for you. . . have you ever written a post distinguishing wearing coloured vs. white t-shirts? I notice anytime I wear a coloured t-shirt in the summer, it really only works if I have shoes with that colour in it, or a piece of jewelry, something else. White however, always looks classy and works. It's got to the point where I only wear white t-shirts in the summer.

    I wonder if wearing a lot of colour in general is like that. You need a scarf, something else, otherwise it just looks cheap many times. . .

  • Imogen, thanks for this post – perfect timing for me since I've just branched out into leggings. If you don't mind, a question for you – what is the longest length of dress you think looks good over leggings? At the knee? Slightly above the knee? I've heard varied feedback, and I'm wondering if I should hem some of my dresses so they are *slightly* above the knee & would work with leggings – but maybe this is silly.

  • Kari – I would suggest that just under the knee is probably the longest (unless you have very long legs. If you have shorter legs, a slightly shorter skirt/dress is always more flattering.

    The least flattering dress/skirt length tends to be low calf.

  • Thanks, Imogen. I am getting mixed feedback about skirt length. Most of my skirts are *at* the knee (not below it) and some people have commented that they look too long for leggings and that I should stick to mid-thigh lengths. Others have said that they are fine at the knee. I haven't made my mind up as to what I prefer, but I'm definitely not tailoring my favorite dresses to mid-thigh since that would make them very limiting.

  • You have shared very good ideas. Leggings are always comfortable to wear. Leggings look stylish too. I will definitely try your ideas. Do share more ideas like these. Take care.

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