What to wear with leggings at 60.

UPDATED FOR 2023

12 best looks for Winter Spring 2023

In winter and colder weather leggings are every girl’s best friend.  Here are 12 tops that make a stylish outfit ideal for a woman of 60 or over.

#1 Long cashmere or wool roll neck sweater

#2 Bright baggy sweatshirt

#3 Pull-on tunic top

#4 Oversized button-down shirt

#5 Long cardigan

#6 Twin set – tank top with matching cardigan

#7 Straight top same color as leggings

#8 Hip length blazer or unstructured jacket

#9 Hip length structured jacket with defined shoulders

#10 Slash or bardot neck top with dropped shoulders

#11 Collared shirt under square-cut sweatshirt

#12 Monochrome fitted top under winter coat or raincoat

Leggings are the tightest pants you can wear.  So unless your rear end and tummy are in perfect shape you’ll need to camouflage these areas.

Don’t believe twenty-something fashion editors who tell you that a tight top tucked in can look sexy.  It doesn’t at our age!

Wearable styles for all mature women

These style ideas for outfits with leggings are all about maximizing your best features and discretely minimizing those areas of our body we are generally less happy with as we get to sixty or seventy. 

But that doesn’t mean looking frumpy.  Far from it.  All of these styles are cool.  Women of any age can wear them and look fabulous.

Shopping suggestions

Here are my pick of the season’s best tops for the looks I explain below. Click on any image to get full details and price. These are updated items for 2023. Retailers – Chico’s, Talbot’s, Marks and Spencer’s and Boden.

Here’s my list of what to wear in winter and spring with warm leggings.  I’ll explain how to style each idea below the list.

Leggings and a roll neck

This is absolutely the best idea on this list.  Big casual sporty knits are big fashion news and as us older ladies don’t need to change our wardrobe every year to keep up with fast fashion you should definitely invest in this trend.  You’ll wear this outfit for years.

Buy the roll neck sweater in the best wool you can.  Think cashmere for snuggly warmth.  Think merino wool for a smart look.  Think boiled wool for casual style that hangs straight – so it doesn’t emphasize your mid-area curves by clinging.

For the neck look for a simple funnel neck (mock neck) or go for the full rolled neck.  This style elongates the upper body.  It makes the eye focus on your face.  Wear your hair back or in a messy bun up top if you have mid-length or long hair.  It’s important to show the collar for this style to work well.

Leggings and a bright baggy sweatshirt

This is perfect for curling up on the sofa in the evening or messing around at home with the grandkids. 

Notice I mention bright and baggy.  Any old sweatshirt just won’t do the trick.

As with almost all of these ideas go one size larger than you normally take.  These tops need to be big.

If you are ordering online, measure your neck to thigh length so the sweatshirt comes to at least halfway down your behind.  But completely over your rear is best.  See idea #11 if you want to wear a shorter sweatshirt.

This top has to make a contrast with your leggings.  So go for a pattern or a bright solid color.  You want everyone to be looking at your sweatshirt so they don’t give a thought to your hips and legs.  So let your happy side take control when you are looking at pattern and color.  No classic combinations this time girls!

Leggings and a pull-on tunic top

These can be cotton or a blended fabric and work well indoors when the central heating is on.

Easy to pop on with no fastenings or zips you should own at least one of these today.  They are cut wider than a fitted top which is good news for those of us with belly fat (aaagghhh!)

This style is a good opportunity to go for something smarter if you wish.  You’ll find the best look is a modest V neck or, for more va-va-voom, a lower scoop neck.  Again you want all eyes to be on your upper body and a neckline that’s showing some skin, or has a V, can make this happen.

If you choose a plain color – possibly the same color as your leggings – look for embellishment that highlights the neckine.  V-necks this year are showing pearls, jewels, embroidery and more, attached around the edge.  For that low scoop you can wear a necklace such as a simple gold chain and know that it’s your skin that is important, not the top.

Leggings and an oversized buttoned shirt

Button up, button down or button through, whatever you call it, you’re looking for the classic man’s style shirt with collar.

I’ve written a post on the oversized shirt so take a quick look: The 9 best boyfriend shirts if you’re over 50.

Oversized – as you will have gathered by now – is popular again this year.  We’re looking back to the eighties and nineties.  So feel free to push, or roll, up those long sleeves.  Turn up the collar.  Let the shirt hang right down over your hips and end anywhere from low hip to top of the knee.  It’s the shirt your tall boyfriend should have – but probably doesn’t these days (aaaahhhh those were the days – and nights!)

White over dark leggings looks stunning.  Wear with a string of pearls for a smart but cool get-together with friends.  Or sweep your hair back (unless it’s short)  and button the shirt low so all eyes are on your throat and moving south, for a super-casual coffee and gossip with your BFF.

Leggings and a long cardigan

This is the style most likely to be adopted by us.  But, sadly, it is the idea most likely to be done all wrong!

I know. A long warm cardi – you’ve probably even got one already.

Stop.  This long cardi needs to hang DEAD STRAIGHT at the back.  So think about getting a larger size.  If the wool clings to even a suggestion of your rump the cardigan is too small.  So you might even go up two sizes.

Leggings allow you to avoid all the usual lumps and bumps of layers such as side pockets and belts or belt loops.  So a cardigan can fall straight and look beautiful on you, whatever your hip measurement.

No, I’m sorry.  You CANNOT TIE THE BELT if the cardigan has one.  That’s because  you destroy the straight lines at the sides which make you look slimmer.  A tied cardigan belt on any but the slimmest figure makes us look like a sack of potatoes.

You can read more about how to style a cardigan over 50 here.

Under the cardigan you can – heaven be praised – wear any tee shirt or top you like.  We won’t see the sides so it doesn’t matter if the top clings to your flab.

Choose tone-on-tone for the whole ensemble to look minimal and chic.  Or highlight the oblong down your front to look taller and slimmer.  You can do this by choosing the cardigan in the same color as the leggings, then choosing a different color or a pattern for the top under the cardigan.

Don’t bother with a necklace, wear earrings instead to continue that slim front panel upwards and make your eyes look sparkly.

Leggings and a twin set

Look for a cardigan that comes to mid hip and make sure the tank top or short-sleeved knit that goes with it is shorter.

I love twin sets and wear them all year.

You can dress them up – think a cashmere twin set and pearls – or pearl earrings.  Sooo English royalty!

Or you can wear a patterned twin set, no jewelry, for a more casual vibe.

The difference in level of the hem of the cardigan and the top beneath, breaks the line around your body and minimizes the size of your hips.  If you wear just a hip-length cardigan that line seems to continue straight across your tummy and emphasizes the width of your hips.

So keep both parts of the twin set the exact same color and texture for this style.

Leggings and a straight top in the same color

Don’t choose a clingy top.  But wearing the same color from top to toe really helps you look neater, slimmer, and taller.  Beware of bright colors which might be too much for many of us.  Personally in the winter I’d head straight for the racks showing navy or black.

Up-style this simple elegant look with great jewelry , a gorgeous watch or a tied scarf.

You can get ideas for classy ways to tie a scarf here.

Leggings and a hip length unstructured jacket

A casual jacket or blazer in Ponte fabric can be a great top with leggings.  It continues the relaxed style of leggings but adds just a touch of structure around your shoulders and waist so that the clingy cardi look is avoided. 

Wear the jacket buttoned over an fine vest or camisole and make the most of your chest area with a long necklace or pendant.

Or leave the jacket open and display a pretty top beneath. 

Ponchos and ruanas are another way to wear an unstructured jacket. They go from indoors to outdoors, covering your hips and rear is the classiest possible way!

Leggings and a structured jacket with defined shoulders

So far all the tops in this list have had a soft shoulder line.

But if, like me, you have a little fat around your back and top of the arms, then a structured shoulder really helps you look smarter.

But the strong shoulder line also makes the jacket hang better so that the exact curves of your body are almost irrelevant.  It is the jacket’s shape people see, not your shape.

So your wardrobe really does need to have a quality structured jacket – one to wear in winter and one in summer.

With plain dark leggings you can go for a bright color.  Orange or bright pink perhaps.  Or look at herringbones and plaids (tartans).

A rollneck in fine wool or cotton can add warmth and allow you to open the jacket when you sit down. 

Jewelry is optional if you choose a bright color.  Otherwise wear simple jewelry so that the structured lines of the jacket get the chance to be appreciated by your friends.

The Chico zebra print topper shown below is the long form of this look.

Leggings and a slash or Bardot top

This is especially popular in summer when you can get the perfect Breton striped top and look French chic.  But for winter choose a warmer fabric such as a knit.  Look for a square-cut top that emphasises the side-to-side rather than the top-to-hem.

The slash neck (boat neck) helps here.  But the Bardot neck – a little wider, and a little more defined by a fold of fabric – does the job even better.

It’s all about getting the eye to concentrate on your shoulder line and above.

Look for neck edgings that draw the eye.  You’ll find patterned edgings as well as fur this winter, (ooooh I love fake fur in winter!).

This is a sporty, playful look so don’t play it too conservative.

Leggings and a collared shirt under a sweatshirt

This is based on #2 and #4 but the items can be less baggy and the sweatshirt can be shorter.  It’s easy to find inexpensive tops for this style.

The image at the top of this post shows me wearing this combination. You can see more of my Winter 2021-2 Capsule Wardrobe here.

Make sure the sweatshirt is wide enough to accommodate the shirt beneath without clinging.  Leave the shirt hem or tails to hang below the sweatshirt.

This is a great way of hiding your backside but still looking super cool and fashionable.

A cream sweatshirt over a white collared shirt looks confident or choose other plain colors to tone or contrast.  As there’s quite a bit going on with the two tops, the collar, possibly the pushed up sleeves and the dangling hem I would steer clear of patterns for this look.

Leggings and a fitted top under a coat

Want to wear your leggings into town?  Not expecting to remove your coat?  Here’s your go-to look for anything from a socially distanced outdoor lunch to a masked shopping trip to the January sales.

The structure of a coat gives you a good balanced outline.  The top and leggings need to be the same – probably dark – color so they are just glimpsed.  They act as a way of making your body recede and making the coat look really good.

So choose a coat of a different color from your top and leggings.

You can leave the coat open – my preference.  Or you can close it.  The minimal thickness of your top and leggings mean you could even wear a belted – yes even a tie-belted – coat (oh joy of joys when it’s frosty!). 

But don’t expect to look good with a thick knit beneath your coat.  Choose a fine wool or cotton fitted top that clings to you instead.

More about leggings

A while back I did a try-on of leggings with mainly summer clothes looking at how various items I happened to have in my closet looked with leggings. So if you want to see the good, the bad and the downright ugly of outfits with leggings here it is!

If you find my comments on styling useful then take a look at my Mature Style Course.  It’s based around building a seasonal capsule wardrobe that works for your body type, your coloring and your budget.  You learn through simple step-by-step videos.

Take me to The Mature Style Course