9 Outfit Tricks For Transitioning to Colder Weather

That time of year is upon us here in New England…the cold weather is coming. While we’re still hanging on with a few warm days, the mornings are chilly and the temperatures have definitely been making a drop over the past two weeks.

Transitioning to fall and winter clothing means getting to pull out all your favorite boots, your cozy sweaters, and wool socks. But, it also means a lot more planning. Summer weather dressing is easy. Just throw on a cotton dress and you’re done for the day. Dressing for fall and winter takes a little more thought. Not only can the temperature change drastically in just one day, but you spend the day between the cold outdoors and the heated indoors and everything in between.

I used to DREAD dressing for winter and cold weather. But, I learned that a lot of that dread was just because I was missing some simple tricks to make dressing for the cold weather easier. So, today (with the help of some of my favorite Connecticut blogger friends) I’m going to share some awesome transitional outfit ideas to take you right into the colder months.



1. Repeat after me…boots and tights

Boot and tights (or leggings) are my saving grace from pretty much October to March. Not only are they warm, but they are so versatile I can’t even stand it. Throw them on under a dress, with a long tunic, or even a pair of shorts. They immediately take your too cold, bare-legged summer pieces and bring them into fall and winter.

Styling Tip
Consider tights with a little more oomph like these fleece-lined tights that will last you a lot longer and keep you even warming. Plus, have you ever heard more beautiful words that “fleece-lined?” Oh baby!

Another tip? Give your tights a quick spray of hairspray before leaving the house to help prevent any runs or pilling.

Here I’m wearing the Bella Lace-Up Shift Dress c/o of Tobi. This kind of top if PERFECT for pairing with tights and leggings.

2.Add leather pieces

Leather is a perfect addition to any outfit for the fall or winter. Not only does the material scream “wear me while drinking a PSL,” it’s also functional since it’s warm but not too bulky.

Styling Tip
Leather works great when you wear it as a single piece and pair it with a lighter, softer fabrics. This prevents the material from being too overpowering. Try pairing it with a soft sweater like Ilse from @livelearnluxeit did, or throw it on top of your favorite cotton dress like Jenna LeeAnn from @jennaleeannllc did!

Also, don’t forget leather doesn’t have to mean restricting! Try leather leggings (YAS!). I’m wearing the Draw The Line Black Panel Leggings c/o of Tobi below!

3. Layered Sweaters

Layering sweaters is a classic look that’ll take you right into winter. It’s also ideal for these transitional months because you can always remove a layer when the temperature jumps from 40 to 70 degrees in a matter of a few hours (seriously New England, wth? JK love you.)

Styling Tips:
Mastering the art of layering can be tricky. The best trick when you’re layering a closed piece (like a sweater or sweatshirt) on top of another piece is to go from longer to shorter. This means any piece that’s closest to your body should be the longest and they should get progressively shorter as you go out. Just like how Jen from @redwhiteanddenim is wearing a longer plaid top and then pairing a more asymmetrical, cropped sweater on top. Or, rock something a little more casual-chic like Rosa Diana from @rmdiana4, she has a button up that is longer than the sweatshirt she paired on top of it.

You can also see how Rachel from @pinterestingplans (the layering queen btw, just trust me and check out her feed) paired a slightly longer top under this oversized sweater. She chose something with a little detailing as well to give it a little something extra.

4. Cardigans are your best friends

Is there such thing as too many cozy cardigans in your wardrobe? I think….no. The perfect thing to bulk up any outfit for extra warmth.

Styling tip: When layering a cardigan, always layer it on top of a piece that’s shorter. For example how Sandra from @therusticlife has a cardigan that is longer than the blouse she’s wearing underneath or how Jen from @redwhiteanddenim is pairing a long duster cardigan over a shorter tank top.

You can also fake the appearance of the item underneath being short like Ilse from @livelearnluxeit did by layering her cardigan over a top tucked into a pair of high waisted jeans. The key is you want whatever is underneath the cardigan to hit you at a higher point on your mid-drift than the cardigan you’re wearing ontop.

5. Layer your sleeveless dresses/tops

I LOVE when pieces are versatile. I honestly hate having more pieces in my closet than I need (I know, am I even a lady?) It’s the truth though, I think it stems from my strong hate for laundry. Either way, whenever you can make a piece work for all the seasons, I’m ALL ON BOARD. You’d be surprised how much you can incorporate summer dresses and tops into your winter and fall wardrobe. You can layer pieces on top of sleeveless tops or underneath to immediately bring it from warm weather to cold weather.

Styling Tip: When styling with a spaghetti strap tank dress, you can layer a cozy sweater over the top of it. Or, use a button up and tie it off around your waist to give the appearance of a mixed media dress.

Or, take after Rachel of @Pinterestingplans and layer a long sleeve shirt or blouse underneath a long sleeveless sweater top.

6. The “just in case” top

Not only does throwing a button up or sweater around your waist give you that “so casual over here,” effortless vibe, it’s also totally practical. In the colder months of New England temperatures can vary all over the place. Not to mention, you may be going from a warm house to a cold sidewalk to an air-conditioned office (WHY is the air conditioning on in Janurary tho for real?!) in a matter for 15 minutes. Layers are key. This look gives you the added layer just in case you need it.

7. Scarves for Days

Forget diamonds, scarves are a girl’s best friend. It’s amazing what throwing on a simple scarf can do to add to any outfit. Not to mention, they are totally practical – go figure! Whether it’s a simple sheer scarf or a heavier blanket scarf, the added fabric does wonders to help keep you warm.

Styling Tip: Get creative. While wearing a scarf the typical way always looks good, you can get creative with the ways you wear them. Try tying them off like Lauren from @rosesandrainboots or wearing them like a shawl like Rachel from @pinterestingplans


8. the wonder vest

Adding a vest or two to your wardrobe is a must for anyone living in the north. They are so versatile during the weird transitional fall weather months, and can add the extra layer of warmth you need in the winter. Whether you go for a traditional quilted vest like Lauren from @rosesandrainboots or a sweater style vest like Jenna LeeAnn from @jennaleeannllc, you’ll find a million ways to incorporate a vest into your outfits.

Styling Tip: Vests aren’t just for pairing on top of shirts, get creative! Try pairing them with your favorite dress like Rosa Diana from @rmdiana4 did.


A post shared by Jenna LeeAnn (@jennaleeannllc) on

9. Jean on Top

Every girl has the perfect pair of jeans, but jean isn’t just for the legs. Use this wonder fabric on top as well to bring in added layers of warmth. Rock it as a vest like Jen from @redwhiteanddenim or the closet staple jean jacket like Sandra from @therusticlife.

Styling Tip: How to rock jean on top? Try using a different color jean on top than on the bottom like Sandra did with her ombre. Or, go for a totally different color on the bottom like Jen with her army green pants.

How to transition your wardrobe for the colder weather Click To Tweet

There you have it, simple tricks for preparing for the colder weather. Thanks to my Connecticut blog babes for helping out with the amazing style. Make sure to give them a follow.

*this post contains affilate links*

Hey There!

I'm Kallie!

Also known as That Practical Mom

I’m all about helping you simplify the chaos of life so you can slow down and enjoy it.

You may have seen me on:



Woman cleaning dishes at the kitchen sink

Hey there, I’m

Nothing happens around here before coffee, so pour a cup and join me. Here you’ll find life hacks, budgeting, simple DIYs, and honest motherhood.
New here?