Sunday, January 11, 2009

Request #1 - Alison - How to Wear Summer Dresses & Skirts in the Winter?

Alison's question: How about utilizing summer dresses or skirts in the winter? I just picked up a cute shift dress in brown with a white outline banana leaf pattern. It's really cute but the leaf pattern seems summery to me.

Short Answer: Layers!

Long Answer: Although I try not to buy clothes that are strictly for one season, sometimes you just fall in love with an item that screams "summer!" Only problem, it's winter outside. What to do? The trick here is to accentuate the skirt part of a dress (or just the skirt, duh, if it's a summery skirt), and layer the top half to balance out the shoe (we'll get to that).

I have to make a couple of assumptions about Alison's dress (not having a picture): the brown is a medium tone (like a rich milk chocolate), the dress is sleeveless/has straps, the print is bold/large. Hope I'm close.

Edit: here's Alison's dress:
Wow, that is an awesome dress! I would totally own that dress...

Some suggestions/guidelines:

1. Underneath layer: Brown and white can be blah on their own, so start by layering a coloured long-sleeved thin t-shirt underneath. Look for a vibrant colour that's going to compliment the brown, like red, turquoise, orange or yellow or a kelly green. Since brown and white are both neutrals, you can add colour without looking too over-the-top.

With a medium brown, stay away from colours that are going to "muddy it up". Think of it this way: if you were in a dimly lit room, muddying colours are those that are going to be perceived as brown to the naked eye, like burgundy, dark blue, medium to dark purple, forest green, and black.

Also avoid light colours like cream, tan or white, as these will accentuate a more summery look - they'll work fine in the spring, but will not look appropriate for wintertime.

Eg. a long-sleeved red thin t-shirt with a medium scoop neck underneath.

2. Second layer: This could be a few things: a sweater vest, a button-up vest (waistcoat), a pullover low-necked sweater, or a cardigan. Something to cover most of the top of the dress, but still allow the pattern and part of your underneath layer to show through at the neckline. You want this layer to be a neutral - in the case of the brown/white dress, something in another brown tone. You are not looking for an exact match, here, although if you have something in that brown with texture, that would be great.

Eg. a camel ribbed thin cardigan, with the center 3 buttons done up (top one undone, bottom one undone).

3. Belt it: If you have a belt in the same colour family as your underneath layer t-shirt, that will work wonderfully for an extra pop of colour. If not, another neutral in the same tone family will work great. A belt with a nice buckle or some detailing on the belt itself will add visual interest.

Eg. a 1" red leather belt with a silver filigree buckle.

4. Third Layer: A jacket/blazer is going to work best here, and it should be in a neutral colour.

Eg. a chocolate brown blazer, or a denim jacket (denim is a neutral - yes, it is!).

5. Tights: You could add a complimentary colour (in the same colour family) for some visual interest or textured tights in brown. Plain ol' nylons also work when you're not sure. Work with what you've got.

Eg. orange opaque tights or brown micro-fishnets.

6. Boots: Nothing will help your summer dress look more season appropriate than boots. A neutral boot will work best, and knee-high boots will work better than ankle booties.

Eg. Brown leather boots.

7. Accessories: Your belt is one, your boots is one, but you take it up a notch and add a brooch and earrings (you will have quite a lot going on near the neckline already, so skip a necklace). This is where I usually add some fun - dangly earrings, a vintage brooch.

Change it up ideas:

- belt the jacket instead of the 2nd layer
- skip the 2nd layer and just do the t-shirt and jacket
- wear the t-shirt over the dress and add the 2nd and/or 3rd layers
- try a different colour palette for your layering colours (instead of the reds used in the examples, try yellow or turquoise)

Here's an example of winterizing from my closet: my leaf-print shift dress that I bought last spring (also worn here and here):

1. Underneath layer: I've layered my black Alice Cooper t-shirt under the dress. The colours in the dress pattern are: camel, brown, white/cream, yellow and black, so I'm limited to my layering colour (and what I have in my wardrobe), but I want that t-shirt to be one of those colours.2. Second layer: Add the long yellow sweater (not quite the same yellow as the yellow in the dress' pattern, but close enough). My t-shirt's sleeves hang out, and you can just see a bit of the dress at the sweater neckline.
5. Tights: At this point, I would put tights on, but due to this particular pattern, I'd wear plain nylons; brown tights would be too dark, fishnets a little busy with the pattern, and yellow would be too much since I'm already doing a yellow sweater. Camel is an option, but I think it might look weird on the legs, like I'd overdone the self-tanner, ha!

3. Belt it and 6. Boots: I chose a wide belt to balance the length of the sweater. If I'd done a shorter sweater or a vest, a thinner belt would look better. The neutral belt doesn't match any of the browns in the dress pattern, but the texture of the cutout compliments the pattern in the dress. The boots also don't match the dress, but they're also neutral so they go.

"Going" is better than matching!
4. Third layer and 7. Accessories: Add the jacket and the jewelry. I added a black suit jacket instead of brown; I felt that brown would definitely be too matchy for this since I have lots of brown in the boots and belt, as well as in the pattern of the dress.

For a brooch, I added my yellow sunflower - I don't have a gold brooch! I think I need to get one! For jewelry, I added the hammered gold cuff and brown disc earrings (sorry, not visible - I'm without make-up and not quite ready to show the world that, haha).

Some notes about all of this:
- Certain summery things just don't transition well, like very thin fabrics (silk skirts, cotton linings). They tend to cling to tights and hosiery and make you frustrated and annoyed over the course of a day. A slip can help...but sometimes it's just better to save those items until warmer weather.
- Thin layers work better than thick layers. A thick sweater or bulky jacket will overwhelm a summer-weight dress.
- When you have more than 2 colours in a pattern, you're a lot more limited to what goes with it. I wouldn't wear red or turquoise with my above outfit, but with Alison's brown/white, she could add up to 2 colours with it (not including neutrals).

Further thoughts for Alison's dress are welcome, as well as comments on my suggestions.

Edit: Here's how Alison worked this dress for winter:
That is awesome! Well done, Alison! You've got a great pop with that raspberry top and I love the texture and shine of the belt! My only suggestion would be that go with a slightly narrower belt, and do up the buttons of the cardi on either side and underneath the belt (the cardi will lay flatter).

Now that I've seen the dress, I would also consider:
- a plain white or solid colour blouse under the dress, with a jacket on top
- a coloured tight with the brown bootie



  1. Very cool ideas. I'm sending you a picture of the dress. You were right on about the colors. Nice milky chocolate and white. I think I'll try my magenta V-neck tee belted over it with either my brown cardi or a denim jacket and brown tights. I really wish I had dark brown knee high boots, but I may have to try my brown ankle booties. They match the tights. Thank you so much for the suggestions and inspiration. I have another skirt that will be fun to work with your suggestions too.

  2. Great post and some really good tips.
    Who needs so-called experts!

  3. Wow this a FAB post Sheila! Awesome tips! Wearing summer dresses/skirts in the winter really helps to stretch the wardrobe and budget. For me, tights or leggings, a long-sleeved layering tee, and boots are the key.

    Have a good week!

  4. Sheila, you're brilliant. I love this tutorial and the fantastic outfit that it yielded!

  5. Alison, I can't view your blog (one has to be invited) and you don't have an email posted in your profile. Please leave your email in a comment (I won't publish it) and I'll drop you an email.

    Thanks for the added suggestions, guys!

    Alison, a magenta t-shirt sounds great. You need brown boots!

    Trace: thanks for the reminder about leggings (I haven't worn them since the 80s and am not about to start, ha!).

  6. Sheila, I do need dark brown knee high boots. I just have the dark brown DKNY booties I bought probably close to 8 years ago or more. I still love them as much today as when I bought them. I have 2 pairs of light brown boots and an old clunky pair of black knee high boots.

    I have a wish list of both new black and dark brown boots. Also, my "if I won the lottery" list of Louboutin's... HA! Someday, someday.

  7. Ooo, more suggestions. Thank you Sheila! I'll try the white long sleeve too. More ways to wear this dress!!! YAY!!

    Yeah, I do agree with the narrower belt and buttoning up the cardi more. I think that will make the outfit even better.

  8. Alison, you definitely need some brown and black boots - I know it's hard, but you're a bargain hunter and there are some fab deals out there!

    I'm so glad you liked my sugggestions. Thanks!

  9. Great post - I layer over/under my dresses more than I just wear them plain! It is a great way to get extra seasons out of your clothes too1

  10. Hi, Kimberly - welcome! I have just started playing with my dresses this way. I used to be "oh, I can't wear this except in the summer" but that is no longer the case.

  11. You know how I LOVE to winterize!!! I love that dress, I definitely can see why you would bring it into the winter months. Y

  12. HCS: I was thinking of you! I knew you would love this.

  13. So if i have black cotton summer dress with thin white scrolled leaf/flower pattern, do you think i could pair it with a purple cardigan and teal kneesocks and black boots? or would that be too much?

    it's a halter dress, so i'm looking more at layering over the top and just leaving the skirt and some bodice visible vs. using the dress as a jumper.

  14. sati, thanks so much for your comment!

    Yes, absolutely! If the dress is cotton or has a cotton lining, you may want to add a slip underneath, or you'll end up with "tight creep" (annoying). That sounds like a great outfit!

    I've also worn halter dresses out of season with cardigans over them. It's a great way to extend the wear out of them!

  15. Hey! I'm 14. I was wondering what I could do with a summer dress that is brown and white flowered. I have a purple hooded jacket on hand, brown tights... Thanks and I loved this idea!

  16. Hi, Anonymous, thanks for checking out my blog! Sounds like you have some great pieces (you can totally wear brown and purple together). Try doing some layers under and over the dress, using sweaters or t-shirts, leggings, skinny jeans or skirts...even another dress! Good luck and don't be afraid to experiment!


Comments are so incredibly special, and I love them and hug them and treasure them forever. Please feel free to tell me what you think!

I'm not currently able to respond to comments, but I will make every effort to answer questions. I do read every single one, and appreciate your comments.

Please note that comments containing affiliate links spam-y sites, spam comments and anything I deem inappropriate will be deleted.