Dresses and Skirts?

If I had a dollar for every question that comes in about why I don’t wear dresses or skirts, I could retire to the French Riviera. I’m exaggerating slightly, but I do get asked about wearing dresses very often.

I distinctly remember the announcement over the loudspeakers in eighth grade, “Girls are now allowed to wear pants to school.” I was thrilled because the previous rules forced me to fit into a garment not made for my body. Even at thirteen years old, I knew I looked frumpy in almost every skirt or dress style unless they stopped at mid-thigh. (Not today!)

Wide-leg pants, gauchos, or culottes are a “dress” compromise for women built like me. When your top half is a size ten on a good day, and your bottom half is a size four on that same day, a dress will only succeed in making you look like you are wearing a tent.

Styling and fashion is fundamentally smoke and mirrors.

I use myself as an example because I hope that I can help you discover what suits your shape and style personality by honestly sharing my fit and style challenges. The cool girls figured this out in high school or maybe the college years; the rest of us took the next forty years to discover what works best for us.

Today, I’m showing you the dresses and or skirts I’ve owned in the last decade. The skirt below is at least fifteen years old. Dark neutral colors are magical since they form a backdrop for anything else in my wardrobe.

Let’s address short legs with lots of broken veins and thick calves. Why would anyone want to show off their worst features while hiding the best part of their legs? My calves are almost as thick as my thighs. ( 19″ thighs, 16″ calves!)

When I wear straight leg dark jeans with dark pointed toe shoes or boots, and a cropped jacket, it gives the illusion that I am six feet tall and weigh much less than I do. The structure and style of great fitting jeans act as a full body slimmer. Bingo!

I know from living near New Orleans and spending lots of time in Florida, that dresses are the most comfortable tropical weather option. I made a few recent purchases to wear with that in mind while I am enjoying as much time as possible in the deep south.

I want to share these items with you now because they will be sold out when we need them. That’s how retail works! (Swimsuits in January and winter coats in August.)

The tank dress above is available in navy or black. Style it with a cropped denim jacket, scarves, or a light color cotton cardigan. (Please imagine it with nude wedge sandals!) I bought the navy dress above here.

Any garment in wine, Bordeaux, or plum speaks to me. It is a vibrant neutral color that is universally flattering and feminine for almost every woman. I purchased this dress here in Blackberry Wine, Misses size small. (It is available in several colors as well as petites, stalls, and plus sizes.) I will enjoy wearing it all year round for the next decade. It is the perfect feminine foundation to wear with jackets, cashmere sweaters, and ruanas.

I also purchased the above maxi skirt here. It will look super with a V-neck cashmere sweater, a denim jacket, or a moto-style jacket.

The skirt and dresses above were selected because they skim the body without adding bulk from styling details. Seams, ruffles, gathers, or pleats add unnecessary girth unless strategically placed.

You will see me style all these purchases with moto, denim, or other types of short jackets or cashmere cardigans in the future. I wanted you to have a chance to buy them before they sell out.

I’m happy to share why I chose these new purchases. Note that they give me the option of wearing a close-fitting cropped jacket, cardigan, or button-front shirt tied above the waist. Cropped jackets provide the illusion of a more slender waist than the one I possess. My styling goal is always to minimize my top half while elongating my legs. These dress and skirt styles skim the body without adding bulk around the middle or at the bust.

The shopping links in my posts may result in a small commission for me at no additional cost to you.

  1. You look great in all these outfits. I so admire your ability to determine what flatters you and conforms to your style and stick to it. Although my body type is the opposite (pear), I’m inspired daily by your style philosophy and your strict adherence to it. Thank you so much.

  2. Susan, I bought the identical maxi skirt from Chicos in a size 0 about 8 years ago! I wore it with a denim jacket and my highest shoes, but it was not a good look for me because I am only 5’3”. I found that long skirts overwhelm me for that reason, wonder if others have had the same experience? Fortunately, my legs are slim and pencil skirts are my best choice.

  3. Susan, I love your sense of humor! Aren’t you glad you grew up to be a cool girl? Besides most of the cool girls go the opposite direction:). I have the opposite problem as you. I need to minimize my hips and maximize my top! You look beautiful in these long dresses!

  4. I love all of your posts and have learned so much. Thank you!
    I do wish you could find a model (just a regular gal) who is pear shape (smallish bust), 60’s, flabby upper arms (like mine) and show how to dress her in slacks, jeans, dresses for one of your posts. I am still trying to understand the rule of three ration. Thanks again for all of your effort and hard work that goes into each and every post you create.

  5. Susan, thanks for sharing your reasons for buying maxi length dresses & skirts. My favourite look of yours is the one in the tank dress and jean jacket, but I think the slip on shoes look too bulky. Maybe nude coloured sandals with this outfit? Sorry to be critical.
    Marilyn (above) – I’m 5’4” and have one straight knit sleeveless maxi outfit (longer tank & long skirt) in black with thin white stripes. It does seem to overwhelm me, too. So I haven’t worn it much. Last week, I had an eureka moment when a friend encouraged me to try on a maxi navy tank dress marked way down (Eileen Fisher-can you believe it). It was shorter & showed my ankles & a little bit of leg and looked so flattering. Then I remembered what Susan said recently…show your ankles and wrists for a (I think) slimmer and more flattering look. My old maxi skirt will get shortened to reveal ankles. Leave it to Susan to offer such pertinent advice!

  6. Susan your knowledge about fashion, nutrition, travel, and all things beautiful are addictive! Love your blog and how you keep developing yourself.

  7. Susan, you look amazing in all these pics! Can’t wait to see you wearing the latest purchases.
    Please let your sense of humor shine in the book that I so hope you’re working on You possess the writing skills and knowledge for it and we, your fans, so need it!
    Thank you for all I have learned from you and for the years of time and effort you have devoted to us!

  8. You look SO glamorous, especially in the first photo with your black stocking and heels! Don’t be put off from wearing dresses and skirts, you look lovely!

  9. Thank you. Helpful. I used to have great legs but have had both knees replaced. They are now far bulkier and thicker than my natural knees. I also have 2 big puckered scars. Add on some fat and cellulite. Not a good sight. How can I disguise my knees and still manage to be cool in the summer? I am 71, retired, and still care about looking nice, but I have a very casual lifestyle these days. Thanks and God bless!

  10. Susan, after all your explanations about why you don’t wear dresses, I have to disagree. As fashion savvy as you are, you have displayed photos of yourself in the most flattering styles of dresses and skirts (gaucho’s) and you look fabulous in them!

  11. Susan Thank you for all your help!!!
    Is there a tee shirt you would recommend to wear with three quarter length sleeves and length sits at hip bone because Upper arms are getting winkles.

  12. Beautiful beautiful! Makes me want to buy one of those dresses. I am a pant girl, but those are lovely. Thank you

  13. Hi Susan
    Your blog today was timely. I’m struggling to find a mother of the bride dress that is flattering. I’m in my mid sixties. Any chance you could provide ideas for what to look for that isn’t sleeveless, off the shoulder, and low in the back? What a dilemma!

  14. Beautiful selections of dresses and skirts! I purchased the same Bordeaux dress this fall! I will wear it with boots in winter and gold sandals in summer! You are so helpful with styling what flatters each individual.

  15. Like you, I prefer pants to dresses. My thicker waist is not flattered in dresses.
    Thank you for taking the time to research and share your findings with us. Also I appreciate the fact that you answer our questions. I draw inspiration from you on so many things! I agree with the other reader – a book from you would be a great next step (but don’t stop your blog!).

  16. You look so awesome in dresses and skirts because you know how to put them together. I have the same body type as
    you do and I love skirts and dresses only I am only barely 5′ 3″ I love the more feminine look for a change. You are so pretty

  17. Susan I do love your style. My problem is I’m petite apple shape & my middle is my problem. I need to wear shape wear to cover my “sins”. My legs are short but slim & my hips. I always like wearing three pieces, but slim jackets are not comfortable & being comfortable & feeling good in what I wear is very important. I am a widow, 78 years old with white hair cut in pixie style & still like to laugh & have fun. My biggest problem when shopping is finding tops that aren’t too long & cover my midsection. I pretty much follow the rules for looking taller. I shop a lot at Chico’s, Beyond Cotton & Nordstrom. What advise can you give to me other than to loose 10 pounds? Always enjoy your blogs. Thank you.

    Pat Newman

  18. Susan,

    I can so relate to what you are saying! I, too have thick ankles and wide calves. It is genetic on my mothers side of the family. As a teenager I dieted down to a very thin size, but, my legs remained heavy! I almost never wear dresses or shorts because of this. I am so uncomfortable in those types of garments, regardless of the weather. I will wear capris in very warm weather if they are loose and longer in length. I feel much more confident in pants. I love your blog because it speaks to me in a personal way!

  19. You look great in all of the outfits, especially the first and last photos in all black. And, if you don’t mind me saying so, “wow”!

  20. Good Morning Susan! I’m 73 years old and really love your style. I am petite 5 2″ on my good days I weigh 118 on my bad days I can go up to 124. So, I have thin legs the weight I carry is in my breast and of course my middle and arms. So, my question is do I shop for ankle length dresses or calf length dresses. I still can wear short dresses to my knees as luck will have it I still have nicely shaped legs. My husband and I love hiking. But in your post above I love the all three of your posts but the tank dress looks to be calf length. Can I wear calf length without making me look short because oh yeah I am.

    Thank you Mary Topalian

    1. Styling tips for petite gals include; show as much of the length of your legs as possible, tailor your tops so that they stop about mid-hip, not mid-thigh. Knee-length dresses will always be your most flattering choice if you are 5’4″ or less.

  21. The most important post I have ever read ( from you dear Susan )
    The dress in Blackberry Wine is ideal for a wedding party in August 2020!
    Thanks for the inspiration.

  22. I just love the way you look!
    I am just 5’3” and Slim but have really bad veins up and down my legs, these veins can cause my ankles to swell (even though they’ve been treated many times). I feel full length is overwhelming for my height and midi emphasizes my ankles so I avoid skirts or dresses except in the winter with thicker hose and high boots. Any suggestions as I live in Kansas and the summers get pretty hot & humid.

  23. Thank you, Susan, for sharing your fashion knowledge with us. We appreciate all the work you do. Please greet Mr. Mickey.

  24. Wow!! Are you kidding; whatever leg is showing in the above skirts, etc. you look gorgeous. I think if you have a nice sized ankle, you do, I don’t (mine look like trees) you can wear those skirts or dresses showing some ankle.

    I too remember 8th grade: I had no bust, a small waist and big legs. I dreaded swimming and gym because of course the boys would look at us.

    You go girl!

  25. I love your style … so classy! I often take screen shots to save in my photos as reference to put my wardrobe together. Thank you!

  26. I like the idea of the longer dress .where wearing a scarf for short Bolero style jacket works. The mid calf length is horrible. It looks very howdy on me. Thanks for the picks.

  27. I am soooo glad you posted an article on dresses and skirts and hit the looks way out of the park! I love the feminity of a swirling, twirling skirt and had hoped you would tackle the look one day. I think they express an important part of our nature and you just showed all of us how to wear them beautifully.

  28. Thank you, thank you ! This post was so helpful to me and spurred me to action with you saying buy now for summer clothes.
    I have been in a quandary trying to find what I could possibly wear to my daughter’s summer “casual garden” wedding in July in Chicago.
    Your wine colored dress from Soft Surroundings was just the starting place . Mother of the Bride dresses are so over the top dressy and my early searches have been more than frustrating. I can’t thank you enough !

  29. Hi Susan, I enjoy your blog and think you have great style. But that being said, I think you are way too hard on yourself when it comes to your long skirts and dresses. The styles you chose to show in this post look fabulous on you! Seriously! I think ankles in black sheer hose are very sexy with high heels. You should wear dresses more often. Why are we women so hard on ourselves? If I had shown you the those two pics with my face instead of yours in those long black dresses with high heels – you would have said they look terrific on me. You rock those dresses – I’m sure Mr. Mickey would agree!

    1. Please understand that the secret of looking your best is knowing how to play up your best parts and downplay the others. I’m being realistic about my body and sharing my styling tips to help others.

  30. That striped maxi skirt has saved me from donating a recently purchased (on line) that I think looks horrid on me. I am going to do a little restyling and removing the upper part and having a new skirt. It will be a midi, but that suits my tall figure just fine. Thanks. Your skirt looks fabulous on you!

  31. My favorite was the blue and white seersucker sun dress you bought two years ago. It looked lovely on you!

  32. Your tank dress is slit on the side. the one from Nordstrom is slit in the front. Any idea where to get the ones with a slit on the sid?. Thank you Helen Reed

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I share tips and inspiration for using what you already have in contemporary ways. Defining words include effortless, classic, refined, discreet, and elegant. My style is chic, minimal, and timeless with a bit of edge.