Transition Into Fall With Leggings

When it starts to get chilly and you want a little more coverage, leggings are a great way to transition your wardrobe from summer to fall. The recipe for looking fabulous in leggings over 40 is really very simple.

What to wear with leggings and boots

Step 1: Buy a pair of Dark Thick Leggings

Black always works. It’s a very slimming color for your bottom half and it is the perfect neutral backdrop for any other color you want to put with it. You need your tights to be fairly thick and opaque, otherwise it look like you walked out the house in stockings and forgot to put your skirt on. Too much information! You know what I mean?

Step 2: Pair your Leggings with a Long Flowing top

Wondering what to wear with leggings?  Don’t buy a top that is oversized and sloppy and think that is going to work. It won’t!

Find a top that skims  your body and flares outward slightly at the hips. A scoop or V-neck  will lengthen your neck and make you look taller and thinner. A higher round neck can work too, but this is not a good style if you are busty because it is only going to make you look bigger than you already are.

What to wear with lace leggings

Step # 3 Be Sure to Cover Your Bottom

I get a lot of women asking me how to wear tunics with leggings and the one thing I want to say about that, or any top for that matter,  is make sure the top you choose is long enough to cover your bum! That’s an important one especially after 40!

Here’s where the elegance factor comes in.  If your top is rather plain then just add a long cascading sweater, especially if it is the same color as your leggings you create a beautiful, classy, long lean line that fools the eye and makes you look taller and skinnier. (And yes, curvy gals can wear leggings too!)

A cashmere or fine quality sweater always look rich and hangs nicely. You could always try a sweater coat too if this is more your style.

What to wear with leggings and boots

Step 4: Wear Cute Footwear

You have a few choices here… cute booties, tall, flat boots or boots with a low heel. ( High heeled boots with leggings tucked in are trickier because often they can look like you are trying too hard after 40). You could also wear ballet flats. Keeping your footwear in the same color as your leggings will ensure the long lean color line is not broken, which means you will look taller and thinner.

Step 5: Don’t Forget to Accessorize Accessories add instant personality and bring this look to life. You might choose to wear a long pendant necklace, bangle bracelets, some fab dangly earrings, a loose hip belt or a scarf. The key is to add something of interest to this basic uniform to make it yours.

Want to know what to wear with leggings in summer? Let me show you.

How do you wear your leggings? I’d love to know. Disclosure- Black and Gray tops for this photoshoot from Stella Carakaski

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  1. Where would you recommend to get some good thick leggings as I do all my shopping on line

  2. Eva Davies says:

    Hello Deborah – one of your UK fans here! I love leggings and tops but don’t always make the right choice for me – I pick what I like the look of – normally bright coloured tops to match my Indian colouring.

    I am 5′ 2″ with short legs and have got big boobs and what I call ‘menopause baby’ tummy but with a defined waist (I do sound a peculiar shape don’t I?) what would you suggest for me. I need something for the Autumn (sorry Fall) and Winter here in London which is normally a bit cold but quite wet. Smart casual is my normal look.

    Oh and by the way due to arthritic knees and a damaged metatarsal in my right foot I wear orthotics in my shoes so can really only wear lace ups/strapped shoes with a 1 and half inch heel. HELP!

    many thanks

  3. Pam Bryant says:

    Love your ideas. My question is, can I wear these outfits? I am 5,’6 and wear a size 14? Thanks!

  4. I am 55, size 8, and I recently bought a skirt to wear over leggings. I am worried about looking silly. The leggings are black and the skirt is a brown sweater knit that hits just at the top of my knee. I love the look with low- heeled boots but feel like it will scream not-age-appropriate. Should I return the skirt?
    PS I will not wear this to work.

    • Hi Lrimo,
      A skirt over leggings is harder to pull off and also the skirt sounds long. Mid-thigh or a little longer is what you generally need to have the proportions right. If your gut is telling you it is not right, then maybe it isn’t. What about a long top instead? Cheers, Deborah

  5. Love your posts and especially this one as love to wear leggings with tunics and boots. I’m 5ft 7 but struggle as have larger chest and am hourglass shape, what tunics would you suggest? Thank you!

  6. You look Fabulous in leggings! And your tips are so spot on! As an independent stylist with Ruby Ribbon, one of my joys is introducing women to our seamless leggings with a skinny band and our stylish tunics over a cami.

  7. RePaula Tate says:

    I have a fashion question about winter boots. I am 5’9″ 150 lbs. 51 years old. What comfy winter boots are appropriate? Can I wear Ugg Boots?

  8. I am in sales and 50 years old ..I love my leggings and boots..young people are always saying love your style..makes me feel good knowing im still dressing my give me great ideas

    • Hi Valarie, So happy to help. I always say, “When you look good you feel good and life is so much more fun.” I’m glad to see you are getting a kick or of looking stylish and congrats on all the compliments! Cheers, Deborah

  9. Zina Duncan says:

    I can NEVER find tops long enough……PLEASE HELP??!!??!!

  10. Cynthia Anne says:

    Thanks so much for the good fashion advice. You’ve given me the courage — and so many good ideas — to wear leggings in public. My question: Can you recommend brands of leggings that hold up well and look great? I’ve purchased a few that are flimsy and fade quickly after laundering. I’d love it if you could steer us to some great choices in the leggings department! Thanks!

  11. Lezier Noobil says:

    Hi! you are such a beautiful woman and you look young.Thanks for your tips, its great!

  12. Maria Luiza Lima says:

    Hi, first time here and like it a lot. I’m 47 and those tips are very helpful ! Loved the video,thks !

  13. Rebecca Harder says:

    Hi, thank you so much for these tips! I appreciate your great fashion ideas and look forward to more!

  14. Sue Lornitzo says:

    Great Video! Thank you.

  15. Peg Sveiven says:

    Thank you so much. I appreciated the simple guidelines. I especially noted the suggestion of wearing all one color underneith and adding a length of color over. I want to dress fashionably but not look outlandish or faddish or like I’m trying too hard. :)

    • Hi Peg, Thanks for your comment and you are not alone. It is challenging for many to walk the fine line of not dressing too old, too young but just right! Our goal at FAF is to provide helpful tips to help you navigate the tricky world of over 40 dressing! Welcome to our community of like minded Fashionistas!

  16. Love all the longer looks …but the shorter vest? I’ve always heard ” leggings are not pants ” – your bum must always be covered or you’re dressing like a toddler. Is it now ok to show your bum in leggings?

  17. If you feel comfortable and feel good, go ahead. Confidence can make all the difference. My own preference is to wear leggings or jeggings with long boots and leave the sandals/shoes for the youngsters with the fabulously toned bodies.

  18. Now that it is getting warmer (lets hope) what type of shoe can be you wear with leggings?

  19. Thanks for the video with hints on leggings @40. I am 41 and trend a bit younger. I do not admit my age at work, though they know I’m close to 40. My work environment is very casual (jeans are ok), so I wonder what you think about wearing a sweater/sweater dress that is mid-thigh with leggings. It is loose fit on top but hugs my behind.. not bad.. No one else really wears this at work because they take advantage of jeans for casual wear… I like to wear something other than jeans most of the time. d.

  20. I love the jegging tips.

    I guess you just wear a tank or t-shirt under the long sweater.

    My boots do not conform to my calf like yours did. I have some straighter cut cowboy boots. Maybe this will work?…



    • Hi Heather,
      Your straighter cut cowboy boots will work just fine! And yes, you can wear a long tank under the sweater. Glad to hear you liked the tips!
      JoJami and Deborah

  21. I have a beautiful black lace dress/shirt top that is to mid thigh with a jagged hem length, long sleeves and the lacing is quite thick so it’s not real see through. I plan to wear this with a red shirt under or a glittery shirt under the black lace, also black leggings and either black boots or black flats. Could you give me some insight as to which style would be best:
    black lace with red shirt under
    black lace with glittery longer dress/shirt under
    knee length boots or flats
    I will also wear a black belt and of course some jewelry. I am 52 years old and in good shape

  22. Thank you for the Great tips JoJami! I love the leggings and boot look but want to make sure my legs are in tip top shape to pull it off!!

  23. Love your fashion tips. Thanks for creating this website!

  24. Thanks for all the legging information, it’s really helpful.

  25. Hi Diane (Lavender Dreams).. Thanks for you comment. Beware of trying to do a sheer top with leggings…it just won’t cover enough. We think a solid top that will be long enough to cover your tushie is a better idea!

  26. A great friend from the UK and myself (I live in Canada) went out and bought ourselves high heeled, over the knee boots, we love them! Now this was last Christmas so what are your thoughts on wearing these boots with leggings and a long sweater or dress for this season? The boots are black suede and so much fun!

  27. Thanks. I love leggings, so comfortable. What is your thought about short dresses with ankle bearing leggings. Too young? I”m over 50 and love your blog.

  28. Susan LaBadie says:

    What shoes to wear with leggings and a long top. is it only a boot or can you also wear a regular shoe?

    • Hi Susan,
      You can wear a low boot but a shoe is hard to pull off! I have seen a gal wearing a fun lightweight dress and a nice slim heeled pump going out to dinner, but for casual wear you should stick with a boot or baller flat or mens loafer.