Transitional Season Cheat Sheet

season transitional dressing

Whenever the seasons shift, the vast majority of us find ourselves fumbling through our closets, plagued by doubt, unsure if we should dress for the current season, the coming season, or some bizarre hybrid of the two. Because transitional seasons are confusing. Do you dress for the weather or the season?  When do you rotate the coming season’s items into your active wardrobe? How do you look chic and timely when the temperature and time of year are clashing?

I’ve covered a lot of this ground before in previous posts, but I thought I’d boil it down into a quick cheat sheet:

Two-thirds now to one-third then

In transitional seasons, I like to create outfits that have elements from the season that’s ending and the season that’s beginning. A good formula to use is two-thirds ending season, one-third coming season. So entering fall transitional, I’d do chunky sandals, a short skirt, bangles, and a tee (summer) with a cuffed-sleeve blazer and lightweight scarf (fall). A bit more from the closing season than the yet-to-arrive one.

Work those sheers

Just about the only time sheer materials WON’T be useful in making transitional outfits work is fall to winter. Any other time – summer to fall, winter to spring, spring to summer – they’re essential. Sheer hosiery, sheer blouses, sheer scarves all allow for layering and depth without bogging down your ensembles.

Mind your colors

Certain color palettes are super seasonal: Pastels are springy, earth tones are autumnal. If you’re on the shoulder headed into a season, try to keep distinctly seasonal colors to a minimum. They can certainly be in the mix, but they shouldn’t be overdone. For instance, an outfit of orange, olive green, chocolate brown, and aubergine at the end of August might look like you’re LONGING for fall. Throw some ivory or khaki into that mix to lighten it up and keep it transitionally-appropriate.

Mind your fabrics

Certain fabrics are super seasonal: Linen and cotton voile are summery, velvet and heavy wool are wintry. If you’re on the shoulder headed into a season, try to keep seasonal fabrics to a minimum. If you’re headed for spring and the snow is melting, a velvet, cashmere, shearling mix will be overkill. Throw in something sheer, a vaguely springy fabric like cotton knit or denim, and create some seasonal balance.

Don’t sweat it

Look around you. Do you see people in shorts and sweatshirts? Overcoats and flip flops? Of course you do. Seasonal transitions are confusing for everyone, and your peers are in the same boat as you. If you end up dressing too lightly or too heavily on a couple of days, believe me when I say that no one is keeping tabs. Do what you can to dress in a seasonal hybrid style, but expect some missteps. And chuckle at them.

Image via Nordstrom

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  • cora

    layers, layers, layers. When it’s cold in the morning they keep you nice and warm, start peeling them of when it gets warmer and during the evening start piling them on again.
    And I have a few items that are one season only: short summer dresses don’t look good layered, flip flops are hard to combine, same with big clunky boots.

  • Valerie

    Morning Sal! Since I live in the mountains (Washington Cascades) I pretty much dress for two seasons every day :-D. It can be 40 degrees in the morning as I leave for work and 80 when I leave for home. Your tip about color is what I usually lean towards–bright shirt-jackets for summer, with a white shell, dark pants. In fall and winter, jewel and earth tones. Have a great day!

  • Ha, I was just working on a blog post about this very topic! I struggle with this here in Atlanta, because steamy summer-like weather goes on long after I’m in the mood for it. My transitional strategy for this longing-for-fall period is to do things like: still wearing short/no sleeves, but in richer colors; still wearing open-toed shoes, but with a darker pedicure; still wearing open necklines, but with more substantial necklaces; still wearing a flower in my hair, but now it’s a sunflower instead of a hibiscus; etc. Also, when the mornings and evenings finally do start to get cool but daytime temps are still hot, cardigans are key!

    • Dee

      Ha, I lived in Atlanta for one year and was so exctied to move north, know why? So I could wear my fall clothes IN THE FALL! Wearing summer clothes way into fall I didnt really enjoy…but you definitely have figured the way to do it.

  • This is something I struggle with. In college, on the first sunny day after a long winter, you notice all the girls wearing denim minis and flip flops, with goosebumps on their legs because although it looks bright outside, it’s only 55 degrees and it just might snow again by the end of the week. I hate being cold so I try to at least wear cropped leggings or something but I’m often the only one in the room with tall boots and a sweater. As long as it’s not actually spring yet, I don’t feel out of place. I also have a really hard time with spring because of the colors… I never know what to pair them with. I have this one skirt that’s a cool baby blue with flowers and it doesn’t look right with anything. I think scarves and jeans are really good layering pieces that can make you feel warm enough without being seasonally inappropriate. I have a ton of scarves in all different colors, but I find jeans really uncomfortable so i tend to shy away from those. It’s funny how a pair of leggings can seem “too wintery” on a cold day in May, but jeans, which are heavier, do not.

    The fall is easier for me. In late August, the nights are cooler and I can just throw on a cardigan with my sundress and sandals. As it gets a little cooler, I can add a scarf, then boots, then then leggings. Fall colors are a lot easier for me to manage too, and I like covering up in warm, soft clothes. It’s too bad I get so horribly depressed at this time of year or I could really enjoy fall!

    I get all antsy about dressing for the right season too, despite the weather. There’s been a couple times where we’ve had a wacky heat wave in April but I refuse to break out the summer clothes because it just feels wrong.

    • Eleanorjane

      What about a white top with the baby blue skirt? T shirt or short sleeved blouse? and maybe some accessories that pick up either the blue or a colour in the flowers on the skirt?

  • Ah, I wish it were time to transition – we’ve got a couple of months left of hot and humid. Great tips, and very do-able. I look forward to the switch from bare legs to sheer tights!

  • Lisa

    I struggle with transition clothing. Here in NEPA it will be cold in the am but 80 by noon! Sometimes up until November. Or it could snow in October. I have no suggestions. I just want to know where to get those cute polka dot tights!

  • Joni

    I love transitional seasons! One of my favorite combinations is to wear skirts or dresses with boots and socks instead of nylons or tights. I have a few skirts that don’t work with slips and stubbornly stick to tights–I like being able to wear these more than just a few months, plus boots are hands-down the most comfy footwear that I own.

    I also own many lighter-weight scarves–these are great in transitional seasons since they are too warm for summer and too cool for winter.

  • Linda

    My main problem with transitional seasons is that I really don’t wear pants, and my really comfortable footwear is pretty much all sandals or boots. That gap when bare legs and sandals are too cold but tights and boots are too warm is the worst.

    • Sal

      I feel ya, Linda. Sheer tights can help since they can be worn with both boot and sandals … but if the weather is in the middle, sometimes that just feels funky.

      • Elizabeth

        I’m similar. My solution? Comfy Mary Janes. They bridge the gap.

  • LinB

    Weather. I dress for weather and time of life. Which means that I almost never choose to dress for warmth unless the weather forecaster tells me I might get frostbite if I don’t put on a coat. Color is how I move among the seasons — I still opt for cotton and linen all year long everywhere on my body except my feet. Feet get woolen socks in winter. Any sweater, scarf, mitt, hat is woolen.

  • Anne

    Thanks for all the great tips. Fall is my favorite season, but where I live, It doesn’t show up until Thanksgiving. During those transition times I always suffer from packed-closet syndrome where I try to prepare for every weather possibility. I think I will work on the 2/3s-1/3 rule and see if that helps.

  • Marlisa

    Love this! The 2/3 to 1/3 bit is an especially brilliant approach. Thanks for sharing!

  • Mel

    Overcoat & flip flops? That’s soooo me! I LOVE flip flops. I have a wide foot; fun shoes are impossible to find, but fun flip flops are all over the place & not too expensive.

    I wear them as long as I can, until it snows. The same with crop pants & capris. I wear them as long as I can into the fall.

    I’m the only person in the office still wearing fancy flip flops and crop pants
    the first day it snows.

    • Heh, do you live in California? Bec. that’s pretty much our uniform 😉 Overcoat & flip-flops *is* the Cali winter look!

      • Anne

        Oh, that is sooo the going look in my neighborhood during the wet season. Only thing that tops it is the shorts with Sorrels that was popular when I lived in the Sierras.

  • Mel

    Forgot to say…I love the tips! That 2/3 vs 1/3 thing sounds interesting. And I hadn’t really thought about sheers other than for summer.

  • AJ

    I want fall so much. My favorite colors – teal, purple, deep oranges – are all autumnal, and I lean towards textured fabrics like tweed, too. And boots. By the time August rolls around, I’m so very tired of light fabrics and summer colors, and I want to wear, for instance, my magenta dress with tights and boots.

    Of course, by the time spring rolls around after winter, I’m desperate for sandals and floating cotton, so maybe I’m just seasonally impatient.

  • Holly

    Hi Sal, I live in San Jose, CA. Our seasons don’t change so much compared to yours (high of 60 in winter, high of 85 in summer). I had never thought so much about dressing seasonally beyond the obvious “you need a light jacket in winter”, “wear shorts in summer”. Last year your summer black out inspired me to rotate out my black stuff in the summer. I will continue to think about my oranges and purples and greens and when I would like to deploy them. You have also inspired me to wear more skirts as you have posted so many cool looks. Keep up the tips!

  • Ruth

    I live on the coast in southern California, and I always dress for the weather. The traditional seasons for clothing just don’t make much sense here because we don’t have four seasons of weather. We have two seasons, and they aren’t all that extreme, so I have a lot of things I wear year-round. I’ll wear the same long-sleeved cotton shirt and light-weight jacket on a sunny day in January and a cool day in June. And when we get Santa Ana winds and it’s 80 degrees in February, I do what everyone else does and wear my “summer” clothes. I sort of do the seasonal color palette thing; I stick with the autumnal colors that are my favorites, but I’ll wear the lighter-colored versions of them in the spring and summer. I don’t observe this as a rule, though, and I don’t know anyone else here who does either. And I wear bright true red year round because it is easily my best color and it makes me feel great.

  • Great tips, Sal. I am especially looking forward to hosiery … though in Texas that will be more like late Oct / November! Since our winters are not that cold, I wear alot of my summer skirts and dresses nearly all year, but with layers and boots and tights in the winter.

    I will start wearing my cowboy boots with my summer florals in a few weeks though! That’s always a fun one.

  • Elizabeth

    I’m always longing for Fall and probably always look it. And that’s okay with me!

  • My mother is incredibly unfashionable. She dress well, in her own way, but it wasn’t till I was in my early teens and started frequenting the blogging world that I learned about all the rules and seasonalities of thing. In consequence, I tend to ignore them. My wool sweaters may be out of place in August, but I’m comfy and I love them, so who cares. I wear what feels right and makes me happy, year round.

  • Boots. I’ll be adding boots (mostly riding) to everything when it comes time to transition for fall. And I’m super excited about it!

  • Dee

    I have a number of outfits that work well in spring and fall — that are just too light for real cold winter and too warm for summer. I live in the midwest and walking is a large part of my commute so I will get very uncomfortable if I don’t dress for the weather. I am pretty much a stickler for winter vs summer fabrics, no wool or fleece or velvet (or turtlenecks!) for me after March — I dont care HOW cold it is, I will layer in mid-weight fabrics. By the same token I dont wear linen or sheer cotton fabrics after mid September or so. I love summer clothes and I love winter clothes (tights, boots, sweaters) too, but its so much easier to dress in the warmer weather — no worries about socks, tights, hats, coats….Great topic Sal!

  • I check the weather forecast for the week when menu-planning, and the night before for dressing (and sometimes again the morning of, just to make sure things haven’t changed). And it’s an old and boring approach, but I live in the NW, so my response to transitions is the same as my response to every day dressing: layers, layers, layers. I’m rarely out and about without a scarf and a sweater of some kind (excepting the few brief weeks of 80+ degree days here) tucked into my bag.

  • Eleanorjane

    I think shoes are a key seasonal item – I see people wearing dark winter clothing with strappy sandals and it jars on me.

    Good tips above. One I use a lot is a thin long sleeved top under my more summery tops and blouses. I have quite a few of these tops and they help me keep warm (can also wear a soft wool singlet, I swear by those, wear them all winter…) while wearing some lighter, fancier tops.

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  • I was reading this thinking “wait, there’s a transition between fall and winter?” Then I remembered I’m in the Pacific Northwest and most other states actually have all four seasons.

  • Vildy

    I read all these seasonal transition things as a matter of course – my closet feels like it’s bursting with options then. But you’ve got some genuinely new to me stuff: the proportional rule between old and new season and the utility of sheers. Brilliant.

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  • patterned tights like above are great for transitioning! i need to stock up on them, I adore ’em greatly.

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  • Sue

    So glad that I found this site! I have an interview next week (first weekend in October) in Rochester, MN. The position is part administrative/part equine care and equine therapy related. For the interview which will take place on a farm, I want to appear business-like, but I’ll be walking around on a farm! A bit of a dilemna. Also, I will be traveling from my current home southwest of Tucson, AZ. My clothing is quite different from what I will be wearing in MN. Can anyone suggest a great outfit for early fall, business casual I suppose in this situation? Any advice will be much appreciated!