14 Chunky Loafer Outfit Ideas for a Chic Winter Look

Trendy winter street style with chunky loafers, black blazers, and modern mini skirt outfits.

If there’s one item that’s having a major moment in the fashion spotlight, it’s the chunky loafer. These shoes have become insanely popular, and they’re especially in demand as people prep their wardrobes for the winter months.

Here, I’m sharing a handful of ways you can style these shoes. From casual hangouts to work-appropriate ensembles, this post should help you nail exactly what to wear with chunky loafers.

1. Plaid Shirt + Distressed Denim

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I am all about a timeless combo, and this one is a total classic. A plaid shirt paired with some distressed denim just works for a casual and rugged feel.

I love how the laid-back energy of the plaid shirt goes so well with the edgy style of the ripped jeans. It makes for an outfit that’s both versatile and stylish.

2. Mock Neck Top + Wide-Leg Trousers

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For a look that feels effortlessly chic, you can’t go wrong with a mock neck top and wide-leg trousers. It’s such a sophisticated yet comfortable pairing.

The sleek shape of the top is a perfect match for the flowy feel of the pants. This gives you a polished look that I think is perfect for going from daytime to a night out.

3. Camel Coat + Sweater Dress

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This combination is just so elegant. A camel coat thrown over a sweater dress gives off such sophistication and warmth.

I find that the neutral color of the coat is a beautiful complement to the cozy vibe of the dress. It’s a classic and refined option for the cooler months.

4. Jacket + Midi Skirt

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I love this for a stylish and eye-catching look. Pairing a faux fur jacket with a midi skirt brings together glamour and a little romance.

The luxurious feel of the jacket adds a touch of elegance, and the midi skirt provides a silhouette that’s both flattering and feminine.

5. Denim Jacket + Velvet Leggings

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Here’s a great mix of casual and luxe. A denim jacket with velvet leggings finds that perfect sweet spot between comfort and style.

The relaxed feel of the jean jacket is a great counterpart to the rich texture of the leggings. This creates an outfit that you can wear for so many different occasions.

6. Turtleneck + Skinny Jeans

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A turtleneck with skinny jeans achieves a really nice balance of chic and practical. You get warmth from the snug fit of the turtleneck, and the skinny jeans add a sleek shape with some modern flair.

It’s a combination that’s both fashionable and functional enough for your everyday life.

7. Chunky Knit Sweater + Leather Pants

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This is such a stylish contrast. You get warmth and a little bit of an edge when you wear a chunky knit sweater with leather pants.

The oversized, textured sweater has such a cozy feel, while the sleek pants bring in some sophistication. To me, this is such a chic outfit for colder weather.

8. Puffer Jacket + Cargo Pants

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This is a super stylish and utilitarian outfit. A puffer jacket and cargo pants bring together practicality with an urban vibe.

The warm insulation from the jacket goes so well with the functional and relaxed fit of the pants. The result is a look that feels contemporary and cool.

9. Cropped Sweater + High-Waisted Jeans

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Such a playful and on-trend look! A cropped sweater and high-waisted jeans make a stylish duo that really highlights your waist.

The shorter length of the sweater adds a modern feel. At the same time, the high-waisted jeans give you a flattering and timeless shape.

10. Sweater + Corduroy Pants

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This pairing is cozy, casual, and a true classic. A warm sweater with some corduroy pants just radiates comfort and laid-back style.

I love how the sweater’s softness works with the textured material of the corduroys. It creates an effortlessly relaxed look that’s ideal for cool days.

11. V-Neck Pullover + Boyfriend Jeans

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This outfit is so effortlessly relaxed. A V-neck pullover with boyfriend jeans makes for a comfortable and easygoing look.

The loose fit of the pullover goes perfectly with the casual and slightly oversized cut of the jeans. It’s my go-to choice for a relaxed weekend day.

12. Oversized Cardigan + Leggings

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For a totally relaxed and easygoing vibe, an oversized cardigan with leggings is the ultimate in comfort. The loose, draped cut of the cardigan creates a laid-back feel.

When you put it together with stretchy leggings, it turns into the perfect go-to outfit for a cozy day at home or a casual trip out.

13. Flannel Shirt Dress + Tights

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I love how versatile this outfit is. A flannel shirt dress with tights is a cozy and stylish pick for colder temperatures. The dress itself has a relaxed and casual energy.

Adding the tights gives you both warmth and a chic final touch.

14. Cowl Neck Sweater + Jeggings

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This is an ideal look if you want to be cozy but still sleek. A cowl neck sweater with jeggings has just the right mix of comfort and style.

The sweater’s draped neckline adds a bit of sophistication. The stretchy jeggings let you move easily, which makes for a polished but still relaxed outfit.

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