Real Outfit Roundup: 7 Casual Winter Outfits

by - January 10, 2021

Whew, the last two weeks have flown by! From finishing up the January magazine to celebrating New Year's to starting the February issue and distribution, I've been pretty busy. Then, of course, there was everything that happened on Wednesday, which honestly sent me into a tailspin of sorts, but we won't talk about that here.

Before we dive into these seven outfits, there are a few promotions happening at Old Navy right now that I thought you should know about considering a good chunk of what I'm wearing came from there anyway.

Back to our regularly scheduled post. I had every intention of taking a photo of every outfit I wore, but then life happened and I legit spent last weekend in pajamas, so I ended up with only a week's worth of photos. Let's get to it.

Sizing info: I'm 5'2" and about 150 lbs. Unless otherwise noted, I wear size 6/8 or medium in tops and dresses, size 6 in bottoms, and size 7 in shoes.

bootcut jeans and sweater

I don't know the reason, but I've found myself reaching less and less for my skinny jeans these days. I really like the silhouette of a good pair of bootcut jeans, and this pair from Cato is really nice. They're high-rise but they don't go above my belly button. I like the double button feature, but they do still have a zipper. They are at least two inches too long on me, as is the case with most bootcut styles, but that's not a big deal since I would never wear them with flat shoes anyway.

My sweater is by A New Day at Target. It's from last year but they always have this same style, as well as a v-neck version. I can't find the crewneck on the website so I linked to the v-neck, which is nearly completely sold out, unfortunately. I really like this brand of sweaters because they're the perfect thickness for our typically mild winters. My boots are also old, so I linked to the closest style I could find.

Outfit Details
Sweater: Target (similar)
Jeans: Cato (exact)
Boots: Old Navy (similar)

boyfriend jeans and sweatshirt

This outfit screams "mom" doesn't it? I think it's the white sneakers. The silver glitter on the heels makes them more fashionable, but you obviously can't see that from this angle. Oh well. This sweatshirt is still one of my favorites. The grey leopard print makes it interesting while the sweatshirt material ensures that it's comfy. And we all know how much I love these boyfriend jeans. They've been marked down to under $30 but sizes are going quickly!

Outfit Details
Sweatshirt: Old Navy (exact)
Jeans: Old Navy (exact)
Shoes: Amazon

maxi dress and moto jacket

I wore this to have lunch with a friend. I wanted to feel dressed up without making a huge effort, so I topped this dressy-casual maxi dress with my grey suede moto jacket. This jacket is vegan so it's a little pricier than I normally consider for a jacket that is literally just for looks. It's on the thin side but has a liner. It comes with a belt around the bottom, but it was way too long so I just took it off.

My ballet flats aren't an exact match to the colors in the dress's pattern, but they're close enough. I almost didn't keep these because they were so tight when I first tried them on, but they stretched out after a few hours of wear. If you've got wider feet, I would definitely size up. If these had been available in a 7.5 I would have exchanged them.

Outfit Details
Dress: Old Navy (exact)
Jacket: Lulu's (exact)
Shoes: Old Navy (exact)

leggings and slouchy sweater

This is what I wore on New Year's Eve. I honestly can't remember what I did that day other than prep my food for the next day's lunch. I keep referring to these pants as leggings but they're technically ponte-knit pants. I wear them like leggings though because that's how they fit. They are much thicker than leggings, however, and hold their shape better. They are a little long on me, but I just roll them under or tuck them into boots. They make my ass look fantastic.

These moto boots have become my go-to in the last month. My mom hates them, LOL, but I love them. They are so comfortable, and the buckles add just the right amount of visual interest. They also feel very on-trend right now, and I like how they add a little bit of edge to my outfits.

Outfit Details
Sweater: Amazon (exact)
Leggings: Old Navy (exact)
Boots: Shoe Carnival (exact)

leggings and warm sweater

I'm honestly not even sure if I would call this an outfit, honestly. I hadn't slept much the night before and had a mile-long to-do list. I can say with certainty that I did not leave the house. I honestly don't think I even put on shoes.

Outfit Details
Sweater: Old Navy (similar)
Leggings: Old Navy (exact)
Socks: Amazon (exact)

boyfriend jeans and cardigan

This was a really hard day, to be honest. After another night of practically no sleep, I had decided to take a nap after dropping Alexis at school and just starting work a couple hours late, but my magazines were delivered that day so I had to get ready for that. I just wanted to be comfortable since I felt like I was going to pass out at any moment. Note: I cannot find my sweater, and I haven't seen anything that's remotely close to it.

Outfit Details
Sweater: Old Navy (sold out)
Jeans: Old Navy (exact)
Shoes: Old Navy (exact)

sweatshirt with shorts and tights

This was hands-down the most head-turning outfit I wore last week. You should have seen the looks I got at the post office, ha! I think the fishnets and combat boots might have been the determining factor there... But I was comfortable and shorts are so much more practical than a skirt when you're moving around a lot.

Outfit Details
Sweatshirt: Walmart (exact)
Shorts: Target (similar)
Boots: ShoeDazzle (similar)

That's all for this edition of Real Outfit Roundup. We'll be back to our regularly scheduled content next week. Until then, enjoy your weekend!

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