I’m very much a “dress for my mood” type of girl. One day, I’m all about chic, Coco Chanel–inspired outfits, and sometimes I’m wearing joggers. And lately? I’ve been wanting to combine both. There’s something about this time of year – you wake up when it’s dark and cold, and all you want to do is throw the covers over your head and stay where it’s still warm (no? Just me?). But alas, you pull yourself out of bed and fight the temptation to throw on sweats, because deep down you know that a cute outfit improves your mood!
Whether that oddly specific example applies to you and you’re looking for outfits that look good and feel good during this time of year, or you simply always prefer styles that strike a balance, this selection of outfit ideas is perfect for anyone who wants to look put-together while still feeling comfortable. The good news is, you don’t have to sacrifice one for the other!
1. leggings + white tee + oversized sweater + oversized blazer + riding boots + neck scarf
I know leggings can get a bad rap – “they’re not pants” – and while I tend to agree, I don’t think they should be written off completely. There are definitely ways to make them look elevated and intentional! My favorite way? Pairing them with looser, longer layers on top. Not only does this balance out the tightness on the bottom, but it also creates a layered look that’s more interesting to the eye.
Start with a high-quality pair of leggings – yes, quality does matter for a sleek, casual look. For added interest, layer a white tee under your sweater. It’s perfect for extra warmth and style. Then comes your oversized blazer. The key here is to add as much length as possible on top while covering your bum – at a minimum. The brown riding boots add a nice contrast to the leggings, and a silk scarf adds a pop of style that pulls your outfit together and places it more in chic territory.
2. sweater dress + knee-high boots + long wool coat
This three-piece outfit combo is one that will never steer you wrong… let’s break it down. First, a sweater dress is one of my favorite hacks for feeling and looking elevated. The silhouette is chic, but the material is comfy and cozy – like being wrapped up in a blanket. It doesn’t get much better than that!
Pairing it with a knee-high boot with a slight heel keeps the outfit in chic territory without feeling too overdressed. Lastly, a long camel wool coat is my secret weapon for instantly elevated looks. The longer length pairs perfectly with the shorter dress, creating an all-around pleasing and stylish look that looks good and feels cozy!
3. leggings + turtleneck + trench coat + cashmere socks + loafers + tote bag
Yes, I’ve got a lot of ways to dress up your leggings! After all, they make a great foundation for casual looks. In this outfit, the leggings get elevated into a casual, model-off-duty look that’s perfect for school drop-off, running errands, or a coffee run. I like to wear leggings at home and then throw on a nice coat when I’m headed out the door. This outfit combo is truly the best of both worlds!
And whether your outfit is casual, chic, or somewhere in between (like these ideas), the little touches matter. Visible cashmere socks add that covetable coziness while dressing down your loafers – mastering the stylish preppy-yet-casual look. Other elevated touches, like a leather bag and oval sunglasses, help your leggings feel like they belong in more than just the gym. Plus, the trench coat adds a classic, Parisian-chic touch.
4. white tee + cashmere v-neck sweater + joggers + loafers + socks + wool coat + beanie
Okay, though I did start this intro by saying “no sweats,” I don’t think that joggers quite apply. Sure, they may not be as sleek as leggings or as polished as other pants, but I think they can still create a great casual-chic outfit. Plus, joggers are a bit more elevated than sweats anyway.
Joggers are inherently casual and cozy, so to elevate the outfit and add the chic – well, we’ve got to add the chic. Think luxe fabrics and timeless silhouettes. Pieces like a cashmere sweater (layered over a tee for extra style) and a long Italian wool coat add luxury and quality you can see (and feel). And whereas sneakers would be an appropriate pick for running errands, the combo of socks and penny loafers makes this outfit feel much more elevated. This would make a great winter travel outfit, too!
Related: 10 Winter Travel Outfits That Are Cozy, Chic, and Carry-On Friendly
5. velvet pants + cardigan + loafers + scarf coat + bucket tote
In contrast, these pants might not have an elastic waist, but they’re not restrictive at all. Plus, they’re velvet – so extra coziness there! These pants are perfect for wearing on a chilly autumn or winter day or dressing up for the holidays in a stylish way. However you style velvet pants, one thing is certain: you can’t go wrong by pairing them with a cashmere cardigan worn as a top. It’s a subtle yet unique way to make your outfit feel a little different. Plus, cashmere is perfect when you want to wrap yourself in comfort!
Sometimes the fabrics you wear matter more than the silhouettes themselves. To complete your outfit, try a scarf coat. It has a built-in scarf that adds both elegance and comfort to your outfit.
6. white tee + cardigan + wool coat + bucket tote + cashmere socks + loafers
Joggers again – here to show you the versatility of this casual piece, and that yes, they can look good. Just like with the other outfit, the key is taking a casual piece like these pants and pairing them with more elevated items.
Too many casual pieces would just look, well, casual! Whether it’s a V-neck sweater or, in this outfit, a V-neck cardigan, borrow from your capsule wardrobe to elevate this laid-back staple. For winter outfits, complete your look with a long, chic wool coat – it’s the perfect piece to make your outfits look as good as they feel.
7. turtleneck + fair isle cardigan + sweater midi skirt + oxford shoes
When it comes to creating stylish, put-together outfits that are still comfortable enough that you’d actually want to wear them, a sweater skirt is key. It’s comfy, easy to wear, and still chic (so nice, you’ll see it here twice).
For this outfit – great for a casual holiday get-together – pair it with a turtleneck and a Fair Isle cardigan. Once again, cozy layers are essential for crafting that warm, inviting look! And if wearing anything with a heel isn’t comfortable for you, these Oxford shoes are a perfect alternative. The little bit of shine makes them feel a little extra special, too.
8. leggings + cashmere socks + turtleneck + oversized blazer + bucket tote + cardigan
Leggings, once again – aren’t they more versatile than you think? Paired with cashmere socks, they bring the ultimate comfort factor, while a turtleneck and oversized blazer elevate the outfit. Draping a cozy cardigan over your shoulders not only adds a layer you’ll want to cuddle up in, but it also adds style and visual interest. A chic leather bucket tote and oval sunglasses keep things classy and elevate the look, crafting the perfect casual-chic outfit for weekend errands or shopping!
9. v-neck sweater + sweater midi skirt + knee-high boots
Here you see this sweater midi skirt again, paired with a soft sweater. This brushed cashmere is one of the softest pieces in my wardrobe, proving – once again – that cozy fabrics are key for cozy outfits (at the risk of sounding like a broken record). The suede knee-high boots have a slight heel, adding that chic factor that makes you go ooh la la. Whether it’s the office, church, or a winter dinner date, this is another three-piece combo to add to your rotation!
Looking Good and Feeling Great
Outfits that make you look put-together without feeling like a pain to wear are always nice to have – especially this time of year, when the cold weather and gloomy mornings seem to zap your energy. Sometimes it feels like you have to choose one or the other – style or comfort – but thankfully, you don’t! Save these comfy-chic outfit ideas for the next time you want to look good without sacrificing comfort.
And in the meantime, check out these 11 Fall and Winter Looks That Prove Black Leggings Are More Than Just Athleisure
That is me every day of late fall into early spring…I’m layering as much as I can to fight that urge, but a fleece sweatsuit won today as I wait the 3 hours for my cold damp hair to dry! That deep cranberry/raspberry color is absolutely stunning on you.
I totally get that. I’ve had fleece joggers on more than I’d like to admit. And thank you so much!