Three Comfy and Cute Outfits to Help Beat the Winter Blahs

January in northern NY is so grey and bleak and there’s barely any sun, and it gets to me every year. I always end up wanting to stay in my cozy and warm pajamas, but I know that getting dressed improves my mood and helps me feel less “blah”.

I put together three pretty simple outfits that are still cozy and comfy but put-together enough for wearing all day.

If you prefer video content, watch the reel HERE.

Below each photo, you’ll find links to the featured items or similar options if the original is out of stock, as mentioned in the LTK description. These are affiliate links, so I may earn a small commission if you decide to make a purchase—at no additional cost to you. Your support helps me continue creating content, and I truly appreciate it!

Just because you’re getting dressed doesn’t mean you have to wear jeans! You can elevate sweatpants with a denim button up shirt layered over a long sleeve, gold jewelry, and cute slipper shoes!

Outfit linked HERE.

If you want to wear jeans, they should DEFINITELY be comfy ones! These ones from Free People are my new favorite! They’re lower waisted than I’m used to wearing, but after getting used to that, they couldn’t be more comfortable! The utility seams also make them really cute and interesting. As for my top and bag, I love pairing green and orange together (my two favorite colors) and I finished it all off with my comfy and cute Birkenstock Boston clogs.

Outfit linked HERE.

An easy way to be comfy is leggings! These ones are flare ones (or as we used to call them—yoga pants) and a little different than regular leggings. I paired them with a bright red crewneck, a black puffer vest, and brown mini suede Ugg boots (mine are a lookalike). I finished it all up with a black crossbody and grey beanie! Super comfy and easy!

Outfit linked HERE.

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Color Combos to Wear: Black and Brown

I remember when it used to be a HUGE fashion no to wear black and brown together. I’m not sure why this was a rule (maybe people thought it was too “dark”?!) but I certainly wouldn’t follow it if it still was. I love a good black and brown outfit combo in all seasons! Here are four ways (plus a bonus outfit!) that I’m wearing black and brown together as we head out of summer and on to the cooler seasons.

If you prefer video content, the reel is HERE.

Do you wear black & brown together?

Outfit 1: black denim shorts, brown tank, brown cashmere sweater, and brown leather teva sandals— I love wearing a sweater with shorts on warmer fall days (this is a screenshot of a video—I forgot to take photos of this outfit!).

Outfit linked HERE.

Outfit 2: taupe brown maxi dress, black cardigan, brown leather teva sandals, and matching brown leather bag with a black floral scarf on it—this dress is such a good one (also come in a ton of colors) and transitions into fall so nicely! You can wear it with a cropped cardigan like I am here, or a longer duster cardigan like I did in my outfit round up earlier this week (this is a screenshot of a video—I forgot to take photos of this outfit!).

Outfit linked HERE.

Outfit 3: a brown turtleneck, black wide leg jeans, black Mary Jane flats, and a brown silk scarf —I love a fun wide leg pant! They are such a great silhouette and having fun with fashion doesn’t just mean adding color, it can also mean different silhouettes too!

Outfit linked HERE.

Outfit 4: a brown cotton sweater, black straight leg jeans, and brown blundstone boots—my blundstones are a go-to in the cooler months and I love pairing them with black. Add a cozy sweater on top and you’re good to go!

Outfit linked HERE.

And as a bonus, here is another outfit I’ve worn recently that is also black and brown!

Outfit 5: A little cropped tank is so cute with wide leg jeans! I loved adding the charm necklace for some bling. I finished the outfit with my Birkenstock sandals in this pretty brown color.

Outfit linked HERE.

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Three Ways to Wear Loafers

I’ll be the first to admit that I thought loafers were ugly and not my style. I thought they were too preppy and that there was no way they could fit into my wardrobe.

Well, it just goes to show that tastes change, because I am in love with this beautiful suede pair from Beckett Simonon (gifted). You can read more details on their website, but their shoes are ethically crafted and made to order. They’re incredible quality and just stunning.

I challenged myself to find three ways to style these loafers and I did—all three ways feel comfortable and like “me”, so I think I did pretty good.

If your prefer video content, watch the reel HERE.

I will link everything at the bottom of this post. As always, I use affiliate links to link my outfits. This just means that if you buy something using my links, I earn a small commission, at no additional cost to you.

I appreciate your support more than you know! 🙂

I love this look— the wide leg jeans with the cuff make it so different than a normal wide leg jeans look. The browns are all super cohesive and bring it together.

These barrel leg pants are super comfy and I love pairing green and brown together! The cream cashmere sweater has pulls it all together and makes it a great neutral look.

This outfit is giving Parisian vibes and I’m here for it. The silk scarf is a fun find from our vacation to Cape May, NJ last year (I found a super similar one to link). I also love how black and brown pair together, so the pants were a good choice.

All outfits are linked HERE (including a bigger pair of loafers). Loafers linked HERE.

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What I’ve Been Wearing Lately

Here’s a round up of what I’ve worn lately! I really love the outfits in this post. I feel like I was creative but still true to my personal style and comfort level. I love when all three of those things can come together and I can create an outfit that works!

As always, outfit details will be linked under each outfit with affiliate links. This just means that if you purchase using my links, I earn a very small commission, at no additional cost to you. I appreciate your support! Thank you!

This outfit is super simple— the addition of the colorful scarf really is what makes the look interesting.

Outfit linked HERE.

It truly surprised me how much I liked this outfit— it’s not colors I would normally put together but I love how it turned out.

Outfit linked HERE.

The tones of this outfit are just *chefs kiss* 😚 in my opinion. The warm browns, burnt orange & tans are my favorite!

Unfortunately my pants and sweater are older so I linked similar.

Outfit linked HERE.

I quickly threw this outfit on to take my son to a doctors appointment, but I felt very sporty-chic in it and ended up loving it.

Outfit linked HERE.

I woke up wanting to wear this graphic tee in a winter way and after some playing around I decided to use this dress as a cardigan. I LOVE the pop of red with all the black accents and my light colored jeans ☺️

Outfit linked HERE// Jeans linked HERE (use MARISSA10 for $ off).

I’ve worn this outfit a bunch before and I’ll wear it again— it’s a perfect outfit when I want to be cozy and comfy and not think too much about deciding on an outfit!

Outfit linked HERE.

I own this cardigan in the orange color and love this dark green too! It fits oversized and has a good heavy weight to it.

Outfit linked HERE.

These jeans have quickly become one of my favorites! They have a stretchy and comfy fit and the utility details makes them fun. they fit true to size for a relaxed fit (I’m wearing them in the first photo of this post too!).

Outfit linked HERE.

I received this matching set as a birthday gift and it’s so comfy and cute! The joggers are a great petite length and I love the cropped fit of the hoodie.

Outfit linked HERE.

We went out on a date night and this is what I wore. My dress is very old so I found some similar options, but everything else is linked!

Outfit linked HERE.

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