Seasonal Style Guide: Styling Tips and Outfit Inspiration for Fall and Winter

left: @desiperkins | right: @jennylinnnn

updated: Nov. 2023

“i love fall fashion now, am i old?” -me

I used to not like fall or winter outfits growing up, I was all for itty bitty clothes and warm weather all year long. But, now, I am all for a good coat and boots. I love cold weather fashion so much now. The neutral tones, the accessories, everything is just giving.

As I always say: wear your outfit, don’t let your outfit wear you. Growing up, I used to just throw on leggings and a hoodie and call it a day. While that can be cute, you really have to know what you’re doing in order for it to be cute and let me tell you, high school and college me was not that cute — I didn’t care so much about how I looked, shocking, right?

If I’m being honest, I just didn’t care for fashion or clothes as much as I do now, especially since I have the control to buy whatever I want these days. A blessing and a curse, I might add.

That’s all beside the fact, let me stop rambling and let’s get into the tips and inspo for fall and winter fashion.  

In this blog, I want to share:

  • Easy fall/winter looks

  • Holiday party looks

  • Fall/winter fashion tips

Idk about you, but when it’s holiday season, I like to be comfy as f*ck; I prefer a comfortable outfit any day. However, I still want to look good as f*ck. So, let’s get into how I stay comfortable but still look like the baddest b!tch. 

First things first, accessories. When I say accessories, I mean shoes, purses, bags, sunglasses, jewelry, and makeup. (Speaking of accessories, Ms. Desi Perkins herself has launched a holiday collection of sunglasses so go check them out here!!)If you haven’t already, check out my blog on how to elevate an outfit because that’s basically how we’re going to style a nice fall/winter outfit. The thing that is going to make your outfit stand out and make you feel like that bad b!tch, is the accessories. Fall and winter looks are all about layering, and that doesn’t mean just clothes. Since pieces are heavier, you need to balance it out with your accessories, so as to not look so basic or boring.

For this purpose, we are going to be treating jackets as accessories, too, because let’s be real, a jacket can definitely complete a look, but let’s also keep in mind you might be taking off a big jacket if you’re heading indoors. 

The looks

The easiest and possibly most comfortable outfit is a monochromatic sweatsuit. Just a good ole matching set; sweats and a hoodie/crewneck. Honestly, boohooman has nice sweatsuits for a good price; I personally like the fit and look of men’s sweats and sweatshirts. But, you don’t stop at just that. You’ll need to add one or some of these to elevate a sweatsuit:

  • Vest/coat/puffer jacket

  • High tops/boots with thick, longer socks

  • Sunglasses 

  • Hat/beanie/earmuffs 

  • Matching bag/purse

  • Jewelry 

These are all definitely optional and you definitely can wear just the sweatsuit, but if you add more elements, and make everything one color, it will really stand out. For me, I like to wear boots with a sweatsuit just to elevate it a little more. Honestly, boots can elevate any kind of look- check out this post for more details. 

If you’re not into a sweatsuit, I suggest a jumpsuit, it is a good base and can be styled so many different ways.

If you really want your looks to stand out or if you’re just lazy and want a good look minus the effort, buy a good staple jacket. This can range from a fur jacket to a denim jacket to a leather jacket to a varsity jacket to even just a long coat. Pro tip: an oversized jacket comes in handy. For instance, my favorite fall/winter look is a mini dress, oversized jacket, and boots. 

An oversized jacket is more powerful than you might think and buying one that’s timeless and good quality will make it last longer and you can keep it in your closet forever. 

How to best style your outfits

When it comes to layering, it can definitely be challenging. The easiest look is definitely a monochromatic look-  either the same color or a different shades of the same color. 

Finding pieces with sweater material is the easiest way to get in the fall/winter vibe. A good sweater dress can be dressed up with the right accessories.

Honestly, I think of everything as an accessory. Jewelry, headpieces, shoes, bags, belts, tights, makeup, literally everything. All of these can look good individually, but how can we make everything look good altogether, as a whole. They all go in hand-in-hand.

To make a statement, get some leg warmers! My favorite look right now is a dress, pumps, and leg warmers! It’s so f*cking cute when the leg warmers match the pumps and it just makes it more winter-y vibes.

Rule of thumb, still- accessorize. This is literally the easiest way to make an outfit, an outfit. 

I hope these tips helped and that you are staying warm and cute all fall/winter long. I know if you’re in colder temperatures, layering is the best way to go! Stay warm, stay cute and let me know what your favorite fall/winter fashion tips are! 

xoxo,
kaels

too bad ain’t me<3

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