Dressing Day to Night

Mastering a day to night look is not only crucial, but especially convenient when it comes to obtaining a stylish wardrobe. From working long hours at the office, then running straight to happy hour or date night, knowing exactly what to wear does not need to add any more stress to your day. How do you take an outfit from day to night? Having the right core pieces by combining the perfect balance of casual and class will make your outfit transition a breeze. Here are some of our favorite, Stately Day to Night Essentials to help you mix and match any item that may take you from desk to dinners out on the town.

10 Essential Day to Night items for your closet

  1. Basic Tee
  2. Button down Shirt
  3. Sweater
  4. Dark Denim
  5. Chino pant
  6. Sport Coat/ Blazer
  7. Elevated jacket
  8. Black Dress Shoe/ Chukka Boot
  9. Clean Sneaker
  10. Statement Accessory


White T shirt, blue jeans, grey flannel button down shirt, brown leather sneakers, black bomber jacket, sunglasses, man in black jacket, black shirt, black pants, and black sneakers


To begin, the basic t-shirt (long or short sleeve) is the ideal base layer when it comes to setting the foundation of your day to night date outfit. Having a few in multiple colors is a great place to start. Make sure the fit is not too tight, nor too loose and that the sleeve hits right near your upper arm. This item is the most common day piece that you can also switch out for a polo shirt to add a little more dress to your day. Moving onto a button down shirt, which is a fantastic staple to style, especially when using some color and patterns to add that extra pop to your look. Leave them tucked or untucked, sleeves rolled and even layered. Adding layers is key when it comes to transforming a regular casual look into a sophisticated ensemble for your day to night clothes. So let’s add on top a crewneck or v neck sweater with the collar peeking through to add some nice dimension to the top half of your outfit.

(Learn more about styling your sweaters in a past post, here.) 


White polo shirt, gray v neck sweater, blue slacks, blue plaid blazer, black dress shoes, black belt, man in sunglasses wearing a gray blazer, blue polo shirt, beige slacks, black dress shoes, holding a weekend bag


Next, pair your tops with some dark denim or colored chinos to create a polished look to wear in the office or out for the day. Again, fit is important with the bottoms you choose, as wearing a more fitted pant automatically elevates the proportions of your outfit. When we begin to transition our looks as the sun sets, throw on a blazer or a nice bomber jacket as the final layer to put a magic finish to your day to night look. Lastly, having a black dress shoe, or a clean sneaker makes the whole combination more appealing from top to toe! A chukka boot is a must-have winter item that can also replace a dress shoe and still feel elevated and ready to go. Looking for one more finishing touch? A leather belt takes any casual day to night attire to the next level by really tying together all of these pieces.


gray long sleeve henley shirt, black denim jeans, brown boots, blue collared shirt, khaki pant, blue and gray plaid jacket with white pant and gray shirt, black sport watch, man wearing brown jacket, tan shirt, and white shirt with blue jeans and brown boots


Mixing and matching these essentials is an easy option when it comes to dressing from day to night and a fun way to play around with your personal style. Start with neutral basics, then slowly add more colors and patterns and even different layers when the seasons start to change. Never stress again, when Stately has all of your items covered! 

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Dottie Day
Stately stylist, writer, and designer based in Los Angeles, CA