This outfit is designed for the 80 degree days we’re having right now. But since it’s almost November (how is that possible?) I’m mentally preparing for cold-weather dressing. Like warm, functional layering — not just the kind that looks cute.
This is not my strong suit.
I’m a summer gal through and through — I love dressing for summer and I feel most like myself when I’m wearing summer clothes.
But … I’ve got to learn functional layering at some point! Might as well be now. And there’s no where to go but up, so I’m optimistic. :)
When something isn’t my strong suit, I first tend to look outside of myself for inspiration. Which is why I end up pinning things that aren’t really my style — like that time I pinned a bunch of button front mini skirts, paired with tights and coats, on my Pinterest page about a month ago.
But instead of looking outward, I’ve come up with three little questions that help me look inward. Specifically, they help me examine what worked in the summer and how I could transfer those successes into the fall.
I ask myself:
- When it comes to getting dressed, which season is your favorite?
- Name one piece you loved wearing during that season and list out why it worked:
- What would that piece look like if it was transformed into something appropriate for this season (AKA the season that’s not your strong suit)?
Allow me to demonstrate:
1. When it comes to getting dressed, which season is my favorite?
Summer.
2. Name one piece you loved wearing during that season and list out why it worked:
Dresses (comfortable, no pinching at the waist, easy — all I have to do is throw on one piece and I’m dressed)
3. What would that piece look like if it was transformed into something appropriate for this season?
Cozy sweater dresses — made of something warm and soft like a good wool blend or cashmere.
Obvious as it seems, this round gave me clarity that I should, in fact, not go for the mini skirt, as cute as they can be. I never really wear miniskirts — not even during the summer. I’ve tried and failed a few times, actually. So the chances of finding success with miniskirts in the winter is risky — for me, at least.
However! Since I had so much success with dresses in the summer, it’s a safer bet that I might have success with them in the fall too.
Clarity — all thanks to those three little questions.
Another example:
1. When it comes to getting dressed, which season is my favorite?
Summer.
2. Name one piece you loved wearing during that season and list out why it worked:
Flip flops (flat, easy to throw on, versatile, doesn’t take up much room in the suitcase, unassuming)
3. What would that piece look like if it was transformed into something appropriate for this season?
Based on my list of why it worked, I’m looking for a shoe that’s flat, something I can slip into, and has an unassuming style — it’s basic and not trying too hard to look “cute”. What shoe might fit that bill? Ah — flat Birkenstock clogs!
Cool, right?
If you have a hard time dressing for cooler weather, like me, give these three questions a try. It can also work the opposite way — like if you love dressing for cold weather, but have a hard time in the summer.
It takes a bit of brainstorming, but it can be a helpful hack when you don’t know where to start.
Let me know if it works for you. If you get stumped on a particular piece, share it in the comments — let’s see if we can work together to figure it out!
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Liked today’s outfit? You can shop it and support Unfancy at the same time by using these affiliate links:
01 | Dress (old) | similar | similar in thicker sweater material and a more relaxed fit (made responsibly)
02 | Sweater by Leith (Fit note: I’m wearing an XS) | In case you’re interested, here’s two other ways I’ve worn this sweater lately: A cool, simple, out-to-dinner outfit. A casual daytime, errand running outfit.
03 | Flip flops (old) | similar
04 | Bag gifted by ONA | similar (made responsibly) | similar with zip top (made responsibly)
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xo,
Sorry, quick pedantic thing: I think you meant “strong suit”, not “strong suite”. Love the blog! I’ve been reading for years :) Just wanted to give you a heads up!
Fortunately for me, it’s in the 50s here in Chicago and I will celebrate by wearing my new sweater dress tomorrow. I used to avoid sweater dresses, because they tend to cling around the hips, but this one is an A-line and is very flattering. I’ll wear it with tights and flats.
I have the same problem! Where did you find this dress?? :)
Land’s End. It comes in charcoal and navy and in petite sizes if you are short like me. :)
Good idea! I’m a fall/winter gal, and layering is the one style I KNOW I can do without effort, but I can’t be stylish in summer to save my soul — I’m grumpy in weather warmer than 85 degrees and can’t be bothered to wear anything more than whatever will keep me coolest (and I tend to go for function over aesthetics when I get in that mindspace). I will definitely use this tactic for summer next year!
Haha, I am also totally grumpy in weather over 85 degrees! I always feel like women are complaining about being “freezing,” but I’d take the cold over 90+ degree heat any day. In theory, I love summer, but in reality, I am SO OVER being hot and sweaty by August. I have so much more fun getting dressed for 50s/60s when I know I can enjoy layering!
Fall is my absolute favorite season to dress for. I love layers, scarfs and “fall colors” (aka all year round colors in my case).
My least favorite is summer, because I hate sweating and thin fabrics that make me feel exposed.
This comment is literally what I was thinking while answering the questions from this blog post. Even in summer I love being with long sleeves and long pants, wearing black, grey and burgundy while people bring out all the bright colors.
Great look! Loving the dress :)
x Sarah
http://www.bohochiccafe.com
Caroline, I know you’ll have a hard time answering this, but maybe some of the other women here have something to say: I have a hard time with winter coats. I love cropped bomber-style jackets because they’re comfy and define my (short) waist. They’re casual but a little edgy and masculine. Also, they show off my butt. :)
But a winter coat for me would need to be completely weatherproof. As in, I could climb Mount Everest in it. My bomber jacket is just too short— my legs freeze — and TOTALLY makes me feel like a snow man. I just don’t know what kind of long coat would suit me when they all have the same feminine silhouette. And the most stylish coats are rarely the warmest…
The real problem is that experimenting in winter coats is pretty much impossible given their hefty price tags! Any suggestions? Maybe I just need to go try on a million and see.
It’s something I have to wear for at least 5 months (in Ontario), so I really want something that makes me feel good AND keeps me warm.
I think the key is to look for a jacket that keeps the waist defining aspect of a bomber through belts, waist seams, darts that make the coat cut in at the waist, whatever. If you can´t find one you love and must stick to the bomber-style, then get merino wool underlayers (try MEC) and use what I call the ¨cozy-lock¨ system: alternate layers pulling up and layers tucking down so that your waist stays warm and no cold draught seeps through the zigzag layers of clothing. (e.g. undies up, woolen camisole down, woolen longjohns up, shirt down, pants/skirt up, sweater down). The Mom Edit blog also swears by fleece lined tights, which are worth checking out and I think they have done some cute-but-warm coat roundups in past winters. Happy Winter!
I personally feel awesome in long parkas, plus, everyone checks out your (toasty) bum when you take em off. ;-) This one feels like a bomber with booty warming extension. https://www.thenorthface.com/shop/womens-caysen-parka-nf0a2tb1?variationId=HDA&rrec=true&cm_vc=Certona
But, seriously, go try on a bunch of them, some jackets are a million times more flattering than others.
If you love short, the notorious “puffy jackets” are incredibly warm, and surprisingly flattering, they make me look a lot less like a marshmallow than i thought. https://www.thenorthface.com/shop/womens-jackets-vests-insulated-goose-down/womens-denali-down-jacket-nf0a2tes?variationId=JK3
I’m also a huge fan of long parkas! Although I definitely prefer something longer than that one. I wear the North Face Arctic Parka which I got in a larger size so it covers me all the way to my knees. https://www.thenorthface.com/shop/womens-arctic-down-parka?from=subCat&variationId=DYY&cm_mmc=Google-_-ProductListingAds-_-ProductTerms-_-The+North+Face+Women+s+Arctic+Down+Parka+Coat+Size:+Small+&gclid=CJ_50Yfih9ACFc1ZhgodFuEAAw
Check your local thrift store! I live in Atlanta but saw half a dozen long, warm coats at the Goodwill this past weekend, and the price tag means you CAN experiment. Also don’t be afraid of “men’s” coats – they don’t nip in at the waist, but paired with skinny jeans/pants or fleece-lined tights/leggings or tall boots they’ll read as a nice edge over more obviously feminine styles.
Leah from http://www.thriftshopchic.com
If you are average or above average height, try out coats with a mid-thigh length. Search for “car coat” or “three-quarter.” These tend to have a slightly edgier look than the typical parka or wool coat, and they keep butt and legs warm. If you are going for a wool coat, look for Thinsulate lining. (For whatever reason, designers of traditional wool coats don’t think women actually go outside in cold weather.) As for how to test out an expensive item, thrift stores are a good place (like someone suggested). Also TJ Maxx. Or, just go to a store and try on a whole bunch. I’ve had one like this from J.Crew for 15 years. https://www.jcrew.com/womens_category/outerwear/wool/PRDOVR~49622/49622.jsp) Good luck from New England.
You could either buy a long belted coat (check MEC for really Weatherproof ones) or you could wear a long cardigan Under your crop bomber.
If everything fail, you go “Québec way” : you have a long (very) warm coat for everyday and a less warm but very stylish one for special occasion. ;)
It’s like pulling teeth to get me in a dress or skirt…so of course, what’s my wardrobe full of? Dresses and skirts. Lol at least I figured that out this year and am refraining from buying any more…the bottom line is I think they are really cute in theory and they look great, but I had to MAKE myself wear them.
Flip flops and sandals are a great way to cool an outfit down…so I can wear fall clothes on a warm day and still keep my feet cool….
Oh man! This is exactly how I decided to get my awesome distressed denim skirt, which ended up being one of my most worn summer items. My thinking went like this: I can’t really wear jeans in the summer because it’s sweltering hot, but my jeans are most loved outfit component. At first I thought jeans shorts were what I needed, but after a few tries at denim shorts I realized I really don’t like shorts very much, I just never feel very good in them. But I like skirts! So the knee length denim skirt with distressing (to keep it from looking homeschooled, and that’s because I was homeschooled for 8 years :) ), became my jeans of summer.
I like this method! I have the opposite problem : I’m a Canadian gal through and through and love fall and hate summer. I just feel so limited with coming up with looks that I love without my boots and layers and black jeans. So I think I’ll give this method a try come next summer.
I love this idea! I’ve just started to think about how these three questions could apply to my own style, and I can already see how they might help with the summer-to-winter transition. I love easy, comfy sundresses for summer, too – now I just need to find some sweater dresses I love just as much! And flip flops are my go-to summer shoes, while in fall I prefer my trusty black Tieks flats.
Love this! Thanks for the great advice, Caroline!
I absolutely love the idea!
I’m just like you, a summer girl, and I have such a hard time to find my style at the end of this glorious season (because, well, in France it’s getting cold in October…). I tried your method; I basically love distressed jeans, particularly boyfriend distressed jeans because they’re comfy and give you that “little stylish thing” that picks up any outfit. Unfortunately, I hate being cold, and when your ankles are exposed (with sneakers for instance) it’s a problem. So here’s my major problem, I don’t like winter shoes! Or at least they don’t match what I like to wear (you cannot wear rolled up jeans with booties without exposing a bit of skin). Maybe someone will have an idea or a similar situation. Anyway, thanks for your articles, I read each and any one of them X
Aurora, I have two suggestions, neither of which sounds very chic, but might help. The first is to wear nude, sheer thigh-high stockings under your jeans (or nude tights, the 15 denier type) so that your ankles don’t freeze and you have some kind of coverage, but you can still roll your jeans up and have the look of bare ankles. My second idea, which isn’t for everyone, is to wear a pair of “statement” socks with your jeans and booties. I only ever do this with a relatively plain outfit, but I have, for example, a pair of black and white houndstooth socks (also a couple of other patterned pairs, in neutral colours) that (in my opinion!) look good peeping out of a pair of ankle boots. Neither of these solutions will work in very cold weather, but might help you stretch another couple of months out of your summer jeans combinations.
I don’t know if it helps, but in one of my last posts I was wearing black booties and skinnies, but instead of rolling them up I just tucked them into the boots: http://simpleness.com.br/uniform-part-4/
I guess it worked fine because both boots and jeans were black :) But, I don’t know if it would work with boyfriend jeans. Anyway, hope it helps!
xo
Anne
Hey Aurora! The ladies have some great suggestions, and I plan on wearing socks! Wear (and show) socks with everything this winter — ankle booties, clogs, Birkenstocks. I’ll do a new post soon so you can see what I mean. My go to sock is a classic camp sock. Check out how I style them here: http://bit.ly/2dGYGll :) xo, Caroline
Great tips!
Liv
http://www.livforstyle.net
I have the opposite problem: I LOVE dressing for fall and am quite out of my element in summer. I will try to keep this set of questions in mind when next summer rolls around!
xx, Kaylee
I’m another autumn girl, so this is my favourite time to dress up. The questions are brilliant though, so I will think about them for summer.
Another one who finds summer dressing hard, I think that’s because it’s not often that warm in the UK even drug so-called summer months! I find with layering I have some clothes that I only use for layering rather than on their own. For instance, long line cami tops or long sleeved tees that are quite tight-fitting so they layer easily under other pieces. If it’s really cold I have thermal tops or leggings to wear underneath.
As to winter coats, I have a fully waterproof parka as it’s a proper outdoors coat with a lifetime guarantee, it’s now a great faded navy. For freezing weather, I have a down-filled puffa coat as it is so warm.
Love the dress, I find dresses hard, although I do like sweater dresses. But then they are really just long jumpers!
*during not drug
Hey Caroline, what is the dress you are wearing out of curiosity? The seams are super flattering!
Hey Chelsea, it’s from my 2014 capsule — a dress from Forever 21. :) xo, Caroline
Caroline, I accidentally came across this dress when browsing around into your archives, and I realize again how much I like this site of yours. It’s wonderful and a real revelation to see on a fashion blog someone who is allowing herself to change in style and personality. Look, you wore the dress also here, http://www.un-fancy.com/outfits/spring-outfits/6-6/, but in a totally different way. It’s so cool to see one can recycle pieces without losing the ability and luxury to keep changing, trying and adapting your clothes to your new personality and accents.
My favorite season for dressing is late fall / winter. I prefer sweater dresses with leggings/tights or skinnies with loose sweaters, but it can be a challenge translating these to summer.
Compare a fashion forward loose shirt dress with leggings & booties underneath, maybe with a scarf, to a short sleeved shirt dress with bare legs. The latter makes me feel like I’m in a hospital gown :/. Summer dresses need more tailoring imo and also, rigorous grooming!
That’s not to say I don’t like the overall idea! When I was at a loss about summer shoes, I translated my winter go-to footwear (sturdy booties) to a block-heel sandal with wide leather straps, which suits my tastes way better than your typical ‘dainty’ summer footwear.
I’m the opposite, I hit my clothing stride in fall/winter. Summer is hot and I feel like I run out of options of clothing I’m willing to sweat in quickly. Shorts, tshirt, sandals, done over and over again. Even when I mix it up, I’m uninspired. But I don’t live in Texas either where inspiration would be necessary as opposed to my 3 months of warmth.
Funny, doing your method the reverse way I now understand why I love in fall/winter wearing dresses with sweater on it!
I like dresses
Why? Because it’s a no-brainer, a dress and tadaa you are dressed
How to replicate that when you need to be warm, but can be sometimes in places where you can’t bear being too hot ? Just take off your sweater, and you have a perfect outfit (all that with tights of course !)
Winter is very tough for me fashion wise. I am very sensitive to cold weather and I live in the Northeast. As much as I love summer and summer clothes, during the winter I can’t bundle up enough. Even the fall forces me to ditch my summer style for the winter layers. My morning commute has me outside for over half an hour so I already look like I’m dressed for winter. Tonight I went out to volunteer at a Halloween event for kids, and let me tell you there was nothing about my outfit that even resembled summer. I wore jeans, my leather boots which hit just below the knee, and leg warmers. For the top half I wore a tank top, a long sleeve shirt, a sweatshirt, and my North Face Arctic Parka. I also wore gloves, a hat, and a scarf.
I’m a little late to the game but I had to comment: this is a genius idea!
It just solved my own personal winter problem. I’ve been enjoying fall a lot so far and my favourite thing has been to wear comfy, long sleeve t-shirts with bright patterns on top of my otherwise neutral clothes. I throw on my faux leather jacket when going out and I have a long black cardigan at work that I can put on top if it gets chilly in the office.
Since the past few weeks, it’s now too cold for me to just have a t-shirt on any more so I’ve turned to my collection of neutral jumpers but their blandness just makes me sad and less like myself. So now I know: I need to hunt down some patterned sweaters!
It feels like a rather obvious solution, but it hadn’t occurred to me until now, so thanks Caroline! I’ll definitely use these questions again in the future!