How to Wear Skinny Jeans or Jeggings

If you have thick calves like me, almost all jeans fit like skinny jeans. Most of the time I am instead wearing straight leg jeans. In these photos, I am wearing jeggings by NYDJ via T.J.Maxx because who can resist buying a $134 pair of jeans for $28? (Jeggings are just leggings that are like jeans at the top.)

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Today I am sharing my style guidelines for wearing leggings. I always wear them with a long tunic or even a short dress. I love this tunic by Birdie James. It is from the Birdie James boutique in Hilton Head, South Carolina. In some of these photos, it appears to be black, but it is indeed navy blue.

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Another thing I always try to do is wear leggings long enough to touch the top of my shoes. I am taking these to the tailor to be hemmed today because they are a little too long for me. I wanted to make sure they were not going to shrink before I had them altered. Don’t you hate when that happens? The reason I want the hem to end at the top of my shoes is that my legs are short in proportion to my body. I do not want any skin to show there because it creates a horizontal visual break that makes my legs appear to be even shorter.

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I enjoy wearing heels because I have worn them for most of my adult life, although I am starting to wear more flats during the day. You could get a similar look with a low wedge sandal.

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The handbag is from my friends at Finley House in Blowing Rock, North Carolina. The shoes are old by Jessica Simpson. I am wearing large crystal and silver hoop earrings from who knows where, so I am not wearing a necklace today. Too many accessories worn around my face can make me look like a Christmas tree.

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Thank you for joining us on this journey through midlife and beyond. The second fifty years are indeed the best!

50 Comments
  1. “… can make me look like a Christmas tree….” … that really struck My Funny Bone this morning LOL… have a beautiful day lovely lady …Fran

  2. I like this look. Sometime would you wear an outfit and picture it twice—with tall heels AND short heels to compare the length> Do you find you can wear pants with a shorter hem wen wearing high heels vs. flats. I’d be afraid of hemming it too short and looking like I was wearing high water pants with flats. Thanks!

  3. I avoid round necklines; instead wear tops that have a definite “V” in front, which tends to elongate the neckline. This outfit is flattering on you, but I cannot wear any slacks/leggings that are so closely fitting, as they draw emphasis to my large legs. By the way, I enjoy all your posts!

  4. Great look! I have the longest legs and that has to be dealt with also. I love your Christmas tree remark! I completely agree. IF I wear a statement necklace, I keep my earrings very minimal or none at all. Accessories can overwhelm my small frame. Thanks for another wonderful post.

  5. I wondered why your jeans fit so well and didn’t flare at the bottom. Mine always flare slightly and I hate that look. Now I know. Thanks for sharing.

  6. Love the tip about too many accessories…Christmas tree…ha! If I wear too much, I feel silly and look silly too. Can’t stress enough the importance of covering the lady bits when wearing jeggings or leggings.

  7. As I approach my 60th birthday, I had to let you know that I’m so inspired by the way you’ve embraced turning 60 with your new Website, and also how you’ve mastered the art of looking youthful–not dowdy–yet classy and elegant.

  8. When I wear a long, tunic-type top in clingy material, I want a smooth look across my middle and the extra fabric in fly-front pants will not give that look. From now on, I’m going to try to wear pull-on pants or leggings.
    When I wear longer tops that are made from a different type material, I can wear my fly-front pants but the sideways silhouette is still too bumpy and lumpy across the middle.

    Any suggestions?

  9. I’m at the point where I go to the tailor with half of what I buy. What makes clothes look good is fit and shape. Thanks for explaining your outfits.

  10. Hi Susan, Love your style! Today I ordered my first Covered Perfectly tops. I wasn’t sure how the sizing compares to other brands but hoping it works out. I’m hoping after weight loss to start a new capsule wardrobe in the Summer next year. So trying out CP’s sizing now will help. I hope my tops will look as good on me as they do you! Have a great rest of the day!

  11. I love your new blog but wish I could click on the picture and bring it up closer like the first picture. Gives me a chance to see the outfit or accessories better.

  12. Love the look. You always look wonderful. I really enjoy your blog. Last week I started the Dr Joel Fuhrman diet and I’m down 9 pounds in the last week AND my sugar readings are those of a non-diabetic the last few days. I want to thank you for mentioning the diet in your blog. Thank you for the time you devote to the site – you are an inspiration.

  13. I love to wear leggings and/or jeggings instead of hose. My office is semi casual, so they are allowed. Even at almost 60 I prefer a shorter hemline with leggings instead of a knee length dress with hose. And I have worn flats almost exclusively since foot surgery in my 30’s when the doctor threatend me if I ever wore heels again.

  14. Thank you for starting this new adventure! I haven’t worn leggings because I feel that I am too old. However, I think I might like the skinny jeans. By the way, I am 78 years old but I like stylish clothes.
    Please keep up this new blog, I love it!

  15. I, too, look like I’m wearing leggings when they’re, in fact, straight-legged jeans. Oh, the joys of having shapely legs! I’m starting to wear more heels so as to make my legs appear longer. I love how feminine they make me feel! Thank you for all of your great tips!

  16. Thank you Susan! I have the same problem with my legs, large calves and short legs. I never buy skinny jeans- they won’t even go over my calves. But I will try these, they look great on you, I never would have tried them on my own!

  17. Congratulations on your new website — it is wonderful. (And I am so pleased I can leave comments easily here too.) You made a comment when you were transitioning from FiftyNotFrumpy to the new Susanafter60 . . . someone said you looked older than 50. I nearly lost sleep over that comment because I disagree so vehemently — you look terrific and ageless and inspirational! You are a wonderful example of ” . . . not older, but better.” Thank you for all your help in making me not just older, but better too.

  18. You look nice Susan. I have started wearing jeggings and leggings more lately. I think it’s because there are so many more cute styles in tunic tops nowadays.

  19. I will be sad on the day when asymmetrical tops are no longer available. It’s such a slimming look. And of course, skinny on the bottom is the perfect choice. We can wear skinny jeans and leggings! Thank you for showing the way!

  20. You’ve chosen a super casual look today, love it and love your new-style Blog. I am pleased to learn your tips for short legs. Mine are short in proportion to my body too – my additional challenge is that they are not slim. But every little tip helps so thanks for today’s post, Susan.

  21. Thank you! A very similar tunic has been hanging, unworn, in my closet since spring. I kept pulling it out, then putting it back, thinking at 61, I’m too old. I love this similar tunic on you and I think (and I’m not sure why) the snazzy shoes are just as key as the jeggings! I’m going to wear it today! Love the new blog!

  22. Oh haha the Christmas tree remark!! Thanks for breaking down the details for us- so often the whole is so elegant looks so effortless that having the particulars is greatly helpful. Love your new site- more elegant and lovely like the subject!

  23. I absolutely love this look on you…so flattering. I also love the new blog as I too am over 60. Keep them coming please Susan!!!

  24. Susan,

    I’ve shared one of your above pictures on my Facebook page and summarize in french what you suggested concerning the jeggings.

    Unfortunately, in Quebec, we have no french equivalent to help women over 50 and 60 y.o. to feel comfortable, to keep on being pretty, feminine etc.

    Is it ok with you if I sometimes share some fashion or make up ideas with my french speaking friends?

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I blogged for five years as Fifty, not Frumpy. Now that I am in my sixties, I am sharing ideas and inspiration for using and loving what you already have.

Thank you!
Susan

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