20+ Cute Winter Trip Outfits You’ll Love to Wear This Year

Poncho coats are absolutely perfect for windy day outfits! This brown wool one looks so cozy and sophisticated, and the weight of the fabric means it won’t blow around like a lightweight jacket would. Paired with straight-leg jeans and ankle boots, it’s the perfect combination of style and practicality.

Grey Baggy Jeans + Brown Adidas Sambas + Brown Sweater

Baggy jeans are having such a moment, and they’re ideal for windy day outfits! This brown sweater looks incredibly soft and the whole color palette is so earthy and beautiful. Those Sambas add the perfect sporty touch.

Striped Cute Shirt + Navy Blue Flared Jeans + Ankle Boots

Striped shirts tucked into jeans are foolproof for windy day outfits! The fitted nature means no fabric flying around, and flared jeans are heavy enough to stay put in the breeze. This whole look is so chic and timeless.

Khaki Green Suede Jacket + Black Jeans + Black Longsleeve

Suede jackets are amazing for windy day outfits because they have enough weight to stay in place! This khaki green color is absolutely gorgeous and feels so luxurious. The all-black base keeps everything sleek and modern.

White Top + Navy Straight-Leg Jeans + Leather Brown Jacket

Leather jackets are the ultimate solution for windy day outfits! They’re heavy enough to stay put and always look effortlessly cool. This brown one is such a beautiful alternative to traditional black leather, and the whole outfit has such a classic, timeless vibe.

Navy Plaid Mini Skirt + Navy Jean Jacket + White Turtleneck Sweater

Mini skirts might seem risky for windy day outfits, but this plaid one is structured enough to behave! The navy jean jacket adds the perfect casual layer, and that white turtleneck underneath is so cozy and preppy.

Wool Beige Turtleneck Pullover + Grey Baggy Jeans + Ankle Boots

Turtlenecks are perfect for windy day outfits because they’re fitted and warm! This beige wool one looks incredibly cozy, and I love how it’s styled with grey baggy jeans. The whole look feels so effortless and comfortable.

Grey Wool Cardigan + Jeans + White Tank Top + Ballet Flats

Cardigans are genius for windy day outfits because you can button them up when it gets blustery! This grey wool one looks so soft and sophisticated. I actually have a similar cardigan that I reach for constantly during unpredictable weather days because it’s just so versatile and practical.

Cream Zip Sweater + Light-Blue Jeans + Uggs

Zip sweaters are such a smart choice for windy day outfits! You can zip them all the way up for extra wind protection, and this cream color is so pretty and versatile. The light blue jeans create such a soft, dreamy palette.

Burgundy Sweater + Cream Scarf + Light Blue Jeans

Scarves are essential for windy day outfits! Not only do they keep you warm, but they also add such a polished touch to any look. This burgundy and cream combination is absolutely gorgeous and feels so autumnal.

Beige Knit Cardigan + Navy Blue Jeans + White Shirt

This classic combination is perfect for windy day outfits! The beige cardigan can be buttoned up for wind protection, and the whole look is so timeless and put together. You really can’t go wrong with this color palette.

White Knit Sweater + Brown Mini Skirt + Brown High-Leg Boots + Brown Leather Jacket

High-leg boots are amazing for windy day outfits because they keep your legs warm and covered! This brown and white combination is so chic, and the leather jacket adds the perfect edgy touch while providing wind protection.

Grey Pleated Mini Skirt + Grey Wool Sweater + High-Leg Boots

Monochrome grey is so sophisticated for windy day outfits! The pleated skirt has enough structure to behave in the wind, and those high-leg boots are absolutely stunning. This whole look feels very European and chic.

Burgundy Leather Mini Skirt + Beige Sweater + Brown High-Leg Boots

Leather skirts are fantastic for windy day outfits because they have weight and structure! This burgundy one is absolutely gorgeous, and paired with the beige sweater and brown boots, it creates such a rich, autumnal color palette.

Dark Grey Baggy Jeans + White Top + Striped Navy Cardigan + Uggs

Baggy jeans and cardigans are the ultimate combination for windy day outfits! This striped navy cardigan is so cute and preppy, and Uggs are perfect for those blustery days when comfort is key. I remember wearing almost this exact outfit during a particularly windy weekend last fall and feeling so cozy and put together.

Lorelai Gilmore Vibes with Black Leather Jacket + Flared Jeans + Burgundy Knit Pullover

Yes, this is giving me major Gilmore Girls vibes and I am absolutely here for it! The leather jacket provides perfect wind protection while looking effortlessly cool, and flared jeans are ideal for windy day outfits because they won’t blow around like wide-leg styles might.

Cream Knit Pullover + Brown Suede Jacket + Straight-Leg Jeans

Suede jackets are such a luxurious choice for windy day outfits! This brown one looks incredibly soft and expensive, and the cream pullover underneath creates such a beautiful neutral palette. Straight-leg jeans are always a safe bet for breezy weather.

Denim Mini skirt + White Top + Cream Cardigan + Brown Boots

Denim skirts are perfect for windy day outfits because they’re sturdy and structured! This cream cardigan can be buttoned up for extra coverage, and those brown boots add such a beautiful earthy touch to the whole look.

Navy Blue Mini Skirt + Brown Boots + Green Cardigan + White Top

This color combination is absolutely stunning! Navy, brown, and green together create such a rich, sophisticated palette that’s perfect for windy day outfits. The cardigan provides the perfect layering option for changing weather conditions.

Brown Suede Jacket + White Top + White Flowy Mini Skirt + Brown Boots

Even flowy skirts can work for windy day outfits when they’re mini length! The brown suede jacket provides wind protection and looks absolutely gorgeous with the all-white base. This whole look feels so fresh and modern.

Beige Pullover + Black Leather Jacket + Denim Mini Skirt + Brown Boots

Leather jackets over pullovers are genius for windy day outfits! The leather provides wind protection while the pullover keeps you cozy underneath. This neutral color palette with the pop of denim is so well balanced and chic.

Navy Denim Skirt + White Longsleeve + Brown Suede Jacket + Black Boots

This is such a perfectly balanced outfit for windy day outfits! The denim skirt is structured enough to behave in the wind, the white longsleeve provides good coverage, and that brown suede jacket adds the perfect finishing touch.

The black boots ground the whole look beautifully and create such a classic, timeless feel that works for any season.