Fall to Winter Style Inspiration

I love styling and wearing clothes for the fall/winter. There is so much you can do and so many things you can pair with one another! I wanted to share with me my favorite trends for this upcoming season, and how to transition those fall pieces into winter!

Chunky Knit Sweaters

I am currently obsessed with oversized clothing, but especially sweaters! Whether their turtleneck, mock-neck, v-neck, crew neck - all are so perfect to transition from fall to spring. Adding winter hats and gloves instead of cute panama hats will take your look from chic fall to cozy cute winter! I am also LOVING textured sweaters. Fuzzy sweaters, cotton balls accents, tassels - adding a bit of texture to sweaters really takes it to the next level. Below are some of my top picks from various websites. Click the photos to be taken directly to the sites link!


Jackets are a huge trend right now. If you follow me on Instagram, you know how much I am loving denim jackets at the moment. But realistically, just wearing denim in the winter won’t cut it - not even here in Nashville. There are so many cute options, and sherpa lined items have been an eye-catching one for me. I love moto jackets , leather jackets, denim jackets etc. all lined with some type of faux fur or sherpa material! ‘Teddy bear’ coats are also raved about. I found the CUTEST leather jacket (last photo) that everyone needs immediately. Check out some of my favorite looks below!

Winter neutrals

I will be the first to say I am a huge fan of winter white. With that being said, I am also a cronic black-on-black wearer no matter what time of year it is. Luckily, there are so many new, cute trends happening to take your love of winter neutrals and step them up a notch.

The first row below are a few of my favorite winter skirts. I love playing with texture - like the last photo taking a knit oversized sweater and pairing it with a leather skirt and ankle boots. Don’t be afraid to mix and match patterns or material!

The second row is one of my newest favorite trends and such a fun way to still wear your cute fall dresses/skirt in winter. Pairing a midi/maxi skirt or dress with an oversized sweater and ankle boots is a great transition of fall clothing. Grab your favorite cropped sweater and throw it over picture 3 and add some cute white ankle boots and you’re ready for the day.

The third row is also an easy outfit. Taking a knit sweater dress and adding over the knee boots is such an easy outfit pairing. You’ll look comfortable and put together, but your outfit only took 5 whole minutes to put together!


Anyone who knows and loves me knows the obsession for shoes I have. I don’t know why because I always find a few favorites and rotate those, but I have been trying to incorporate my shoe style with the outfit more frequently! Another thing you would know if you knew me well would be that Target is my absolute obsession and most of my shoes and clothes I get from there. So, a lot of what’s below is either from there or DSW because I would say they are my go-to shoe shops!

Mules and clogs are a great shoe to pair with ankle jeans - or at least that’s what I usually wear them with! You will also find me wearing them with leggings and an oversized sweater.

Ankle boots are a great pair for the sweater/maxi skirt combo we were talking about above! Also the always easy ankle jean!

Riding boots are such an easy wear with any casual fall/winter outfit. Whether you’re just in your winter coat or dressing up a bit for church or Thanksgiving, they’re another cute and casual way to dress up an outfit!

Over the knee boots are my newest love. Pair these with knit sweater dresses, cute jeans and blouse - whatever tickles your fancy and rock them!

I am currently trying out a new app called 21 Buttons and there I am able to directly link my outfit details for you all to shop from or see!

If you’re interested in that kind of stuff, my username is samanthalcostello and I have uploaded a few of my outfit posts from my Instagram to it! You just click the dot on the item of clothing and it will give you the item details. Plus, it is a direct link right to the stores website and that specific item!

If you check it out and like it, let me know! Unfortunately for us new bloggers, we don’t get the fancy Instagram features like swiping up or linking clothing right on the photo. So at the moment that is the easiest way by phone to shop my outfits right from Instagram! You can also always use my “Shop My Looks” tab above here on my blog for pieces but unfortunately it isn’t my photos, just the items photos!

As always, thank you for reading and following along on my little journey. So many exciting things are happening in the next month and I am very excited to share that with you!

Love always, xoxo