Style Guide: How to Put Together a Dressy Casual Outfit

Dressy casual attire (also called smart casual) is a combination of relaxed and refined pieces—think blouses, dress shirts, button-downs, dress pants, dark jeans, and clean shoes. Along the spectrum of formality, dressy casual is one step above casual (jeans and t-shirts) and one step below business casual (office wear like dress pants and pencil skirts).

One of the most common ways to achieve a dressy casual look is to pair pieces of slightly different formality levels—for example, wearing a pair of heels to dress up your jeans, or wearing a blazer to dress up your sneakers.

Dressy casual is an ideal style choice for social occasions without clear dress codes. The style choices in this dress code offer a balance between casual and formal wear, making it a safe option for events like nights out with friends and first dates.

Going out to dinner with friends and not quite sure what to wear? Here are some options for dressy casual outfits for women:

• Tops: Try blouses made of nice fabric or with interesting details, or a collared shirt or button-up—either short sleeves or long sleeves work great. Wear a blazer over your top of choice for added dressiness. Avoid cotton T-shirts or anything with large printed graphics or slogans.
• Bottoms: Non-denim pants like chinos, silk pants, or dress pants are a great choice for a dressy casual look. If you want to wear jeans, opt for slim-fitting dark or black jeans without rips or distressing. In terms of skirts, flowy skirts or pencil skirts work, but avoid pencil skirts that look too structured or have formal details like pinstripes, which can skew too business casual. Avoid pants with holes, rips, or stains.
• Shoes: Oxfords, ballet flats, and loafers work well for a dressy casual look. Try ankle boots, wedges, and low-to-mid heel types. If you choose to wear heels, consider dressing down the look with jeans to stay casual enough. Only wear sneakers if they’re clean. Avoid ultra-casual shoes like running shoes or dirty sneakers.
• One-piece outfits: Sweater dresses, shirt dresses, and sundresses all achieve a relaxed and refined balance. Jumpsuits are a great way to try something more unique; opt for one that belts in the middle to add dressiness. Cotton maxi dresses are acceptable, but avoid other floor-length dresses, which often skew more formal (into festive or black-tie optional territory).
• Accessories: Choose one or two delicate accessories to look polished but not overdone. Simple earrings, delicate necklaces, bracelets, or nice watches all work well.

Headed to a first date and not quite sure what to wear? Here are some options for a dressy casual dress code for men:

• Tops: Button-down shirts are the best way to go, either short-sleeved or long-sleeved. Add a blazer or sport coat over a shirt for extra dressiness.
• Bottoms: Chinos, dress pants, or slacks are all great choices. If you want to wear jeans, opt for slim-fitting dark or black jeans with no rips or distressing.
• Shoes: Loafers and Oxfords are great dressy casual shoes; go for leather for the dressiest look. Only wear sneakers if they’re clean. Avoid ultra-casual shoes like running shoes or dirty sneakers.
• Accessories: Adding an accessory or two will help elevate an outfit and give it a final dressy touch. Nice watches or simple bracelets are a great way to go.

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