Wearing vs. Styling: 10 Fall & Winter Outfit Ideas

Same basics. A few thoughtful details. Explore 10 fall and winter Wearing vs. Styling looks for brunch, dinner with friends, date night and the holidays, plus the original navy-blazer outfit.

Each comparison starts with the same base pieces and adds layers, shoes, belts, handbags and jewelry. Use what you already own and adjust the layers to your weather.

1. Weekend Brunch

A white button-down and jeans get a polished finish with a camel blazer, brown belt, loafers and a structured handbag.

2. Dinner with Friends

Pair chocolate dress pants and a fitted tee with a leather jacket, gold jewelry and burgundy accessories.

3. Fall Coffee Date

An oversized tee and tailored shorts feel more intentional with a tuck, a belt, a shorter blazer and knee-high boots.

4. Date Night

Style a burgundy satin skirt and black tee with a leather jacket, delicate gold jewelry and pointed heels.

5. Holiday Dinner

An emerald midi dress gets a festive finish with a slim belt, cream coat and gold earrings.

6. Winter Lunch Date

Inspired by the cocoa Commando faux-leather leggings in New In My Wardrobe: add a camel coat, cream scarf, tall boots and a chocolate handbag.

7. City Brunch

Style the slate-gray Express Bermuda City shorts with a tucked white button-down, a shorter black blazer and knee-high boots.

8. Weekend Lunch

The chocolate Bod & Christensen Marley jacket inspires this look with dark jeans, a cream tee, a silk scarf and brown accessories.

9. Holiday Party

A black satin dress becomes party-ready with a burgundy velvet blazer, sparkling earrings and gold shoes and a clutch.

10. Winter Dinner

Charcoal dress pants and a fitted ivory tee pair with a winter-white coat and burgundy shoes and handbag.

Bonus: The Original Navy-Blazer Look

A white tee and jeans, finished with the shorter tailored navy blazer, a brown belt, gold jewelry, pointed heels and a structured handbag.

Explore New In My Wardrobe →

Digitally styled outfit inspiration. For featured wardrobe pieces, check the retailer’s original photos and product details before purchasing.