How to Stay Warm in a Dress


Are you new to wearing dresses, and wondering how you’ll manage your first winter as a beautiful, feminine, modest dress-wearer? First of all, congratulations on your decision to dress with modesty. You will never regret looking classy and respectable, and  you will soon appreciate the very significant differences in the treatment you  receive by presenting yourself  as a lovely lady instead of a hot chick. I want to encourage you to make it through the upcoming winter without “growing weary in well-doing,” so I offer you some tips.

First of all, know that YOU CAN DO THIS. There is no question about it! Generations of our ancestors managed their lives wearing dresses in all sorts of weather, without the benefit of central heat, by the way. Most of the time, the adjustment to be made here is psychological in that a dress is not actually impeding your functionality, you simply feel funny wearing one to do certain things. This may be because you don’t own the most suitable type of dresses or skirts for every activity yet, but that will come with time and perseverance. You can do it, and you’ll be so glad you did.

If you work in an office or other indoor setting, please FORGET the idea of wearing dress shoes such as pumps, and leaving your calves bare or covered only by pantyhose (if anybody wears those anymore!). You will be just like some of my silly coworkers, who walk in the door daily in skimpy dress and immediately start complaining that they’re freezing. Be wise about this! The weather won’t change to accommodate your clothes, so you must change your clothes to fit the weather. What you need are some BOOTS. I myself can hardly wait to start wearing boots each year, because for one thing, you can wear your favorite comfortable socks and nobody will ever know, plus you don’t need to be concerned with how your legs look! If your boots seem to look funny, chances are that there is a wrong-sized gap between the top of them and the bottom of your skirt. I think it’s best if there is either NO gap (so your skirt comes down over your boots) or a gap of several inches (if you have that much leg). Just a slight gap looks like a mistake, similar to the look of “high-water” pants. I would caution you, though, when leaving a gap, that “sexy” is not the look you are going for. Keep your skirt at a decent length, and please avoid blatantly sexy stiletto heels. You do realize, my dear innocents, that when you wear shoes like that, it tempts men to picture you wearing ONLY the shoes? I would love to have a man comment and back me up on that, because I am absolutely sure of it.

You are going to want to have skirts or dresses of thicker, sturdier material, that the wind will not cut through. In hot weather, I tend to wear very lightweight, flowing skirts, but winter is the time to change to khaki, corduroy, or thick knits, and denim for casual wear. Obviously, longer is warmer.

Your secret weapon is what you wear on your legs. You will need some or all of the following: tights, leggings, and thermal underwear! Tights are nice when the weather is not biting cold but just a bit chilly, and bare legs would look oddly summery. They are also nice when you don’t feel like boots and would rather wear a mary-jane or some other style of shoe. Leggings are warm and come in all sorts of colors and patterns, but be careful with those patterns if you’re a mature lady. Not all are becoming to us. A benefit to leggings is that they are footless, and since we’ve already decided you’ll be wearing your favorite socks, you don’t want your feet to get all overheated indoors. Thermal underwear is for SERIOUS cold! In the past I owned some actual “long-john” style with the sort of checked-looking pattern. I actually prefer those, because they have a band at the ankle that keeps them from moving around. (Thermal sets are great to sleep in, too, because they stay rather close to your body so they keep drafts from going up your clothes, and don’t get all twisted around as you toss and turn.) Now that I live in Florida where it’s not very cold for very long, I have not been able to find that style, but I have some “Cud’l Duds,” purchased at Walmart, that serve the same purpose.

Finally, if you run low on ideas or have no modest dressers in your daily life that you’d like to emulate, PINTEREST IS A GOLD MINE! Approximately one bazillion people (just kidding) have Pinterest boards labeled “modesty” or “modest clothes” and so forth. I’m sure you could even search “modest winter” or “skirts and boots” or whatever it is you’re trying to work with.

I wish you a wonderful winter and a delightful holiday season…Thanksgiving, Christmas, and New Year! Be beautiful be festive, be WARM, and be modest and classy, too!



19 Comments (+add yours?)

  1. Laura of Harvest Lane Cottage
    Nov 02, 2014 @ 23:33:37

    This was a terrific post for ladies new to dresses. I know that wearing dresseswas an awkward transition for me many years ago, but I wouldn’t dream of going back.


  2. Hazel Moon
    Nov 03, 2014 @ 07:41:44

    I love boots and need to get me a pair. I agree a dress does give a woman a look of class. If you are really cold, there are sweater dresses that are stylish and comfortable. You may need to shop on line. You are a near neighbor at Sunday Stillness


  3. Brittany at
    Nov 03, 2014 @ 13:30:13

    Choosing the right skirt/dress material is definitely key. I used to have some real lightweight skirts, but they were SO cold if it got windy at all. Plus, with skirts/dresses you can always add extra layers underneath.


  4. Toni
    Nov 03, 2014 @ 16:21:18

    Hi there! i’m visiting from Strangers & Pilgrims’ blog. I’ve used the same ideas as you posted for years to stay warm in my skirts and dresses but never thought to post them. That was a great idea, and I’m sure it will encourage some that are newer to dressing in a feminine ways. :)
    Have a great day!


    • Sweet-Water-and-Bitter
      Nov 05, 2014 @ 23:28:42

      Hi Toni, I wanted you to know I returned your visit. I was not able to comment…whatever your comment thingy wants from me, I was not able to provide! LOL But good to meet you and thanks for stopping by.


  5. Jenny (@LittlestWay)
    Nov 04, 2014 @ 16:02:12

    That’s really my only favorite part of Winter is “Boot weather!” I have my favorite black boots and then a year ago my family got me a great pair of cowgirl boots!


  6. jesthepilgrim
    Nov 05, 2014 @ 02:35:12

    I do live in thermals during the winter and find my denim and corduroy skirts serving me well. Being on the farm, I wear the fur lined “Ugg” style boot and all is good. (I also agree with stilettos being a no-no for a believer, my goodness!!!) Thank you for sharing your wonderful posts on the Art of Home-Making Mondays this week! :)


  7. tmpresser
    Nov 05, 2014 @ 03:44:02

    Thanks for a great post, I really enjoy your writing style. So many christian women (girls) just don’t seem to think about how what they wear affects others and their thoughts. I am trying to teach my youngest daughter to dress modestly and to honour both her Heavenly Father and her earthly Father in this. Thank you for linking up at Good Morning Mondays. Blessings


  8. Sweet-Water-and-Bitter
    Nov 05, 2014 @ 22:48:22

    Thanks to all who have commented!


  9. Nita
    Nov 07, 2014 @ 12:00:04

    Thanks for the tips! I work in an office and keep my heels in a bag at my desk. I wear my boots from the car and if I have an offsite meeting, but in my office I am comfortable in my heels. I also don’t do skimpy, not my style, but I do classy (or try to). Friday’s is a jeans and jersey day at work. I’m visiting from Weekly Wrapup.


  10. Beth
    Nov 07, 2014 @ 18:18:54

    Thank you! I loved this post…I may even get a dress and some boots!! I have a feeling I should check out some of your other posts…


  11. mrsktc
    Nov 08, 2014 @ 21:27:49

    Reblogged this on To our bodies turn we then.


  12. dressyalex
    Nov 09, 2014 @ 02:42:32

    I fortunately do not live where there are very wintry conditions, although it can get quite chilly. But the season does afford me the opportunity to don my long skirts and coats.


  13. Shari
    Nov 10, 2014 @ 12:28:35

    “…please avoid blatantly sexy stiletto heels. You do realize, my dear innocents, that when you wear shoes like that, it tempts men to picture you wearing ONLY the shoes? I would love to have a man comment and back me up on that, because I am absolutely sure of it.”

    I have said this for years!!!!!!!!!!!!!! I thought I was the ONLY Christian that felt this way!!!!! When I look back at the history of women’s fashion, I can only find those super high heels connected to prostitutes. (No, I have no data to back me up on that right now). I am shocked SHOCKED every time I see someone I that know is truly a believer wearing shoes like this. Avoid even the APPEARANCE of evil, ladies. I even had to tell a Christian friend that I could not be in her wedding because she wanted the bridesmaids to wear (along with an immodest dress) strappy stiletto heels that wrapped around our ankles. She never spoke to me again.

    As a Christian, I believe that I MUST maintain my appearance in a lovely, ladylike, modest fashion. I want to please my Savior- not the world and certainly not fellow believers. Just Jesus.


  14. Trackback: Titus 2 Tuesday #129 - Cornerstone Confessions
  15. Deborah
    Nov 13, 2014 @ 02:25:11

    Great list! I’m far from Florida and it’s cold here all the time. I love your advice about the leggings–I have several pairs of fleece lined leggings. They are usually under $10. They also make flannel “slips” that can go under your skirts/dresses. And, I LOVE BOOTS. All year! You can wear boots up to your knees or thighs, and no one will ever know.


  16. Deborah
    Nov 13, 2014 @ 02:49:01

    Yes! And tuck them into your bag. Excellent idea.


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