What to Wear When the Dress Code Is “Upscale Casual”

“Upscale casual” is basically the host saying: please look intentional, but don’t turn this into a full suit or cocktail dress situation. It’s close to smart casual, sometimes overlapping with business casual, and the exact line depends on the venue (restaurant vs event), time (day vs night), and how strict the door is.

I usually tell people to treat upscale casual as “polished casual with real shoes”. If your outfit would look normal at a nice hotel bar, you’re in the right zone.

Quick answer for skimmers

• Start with one “structured” piece: blazer, tailored trousers, a polished knit, or a clean midi dress.
• Jeans can work if they’re dark, clean, and not distressed, but they’re not always the safest choice.
• Shoes should look deliberate: loafers, leather sneakers (minimal), heels, clean boots.
• Avoid anything that reads “gym, beach, couch”: flip-flops, graphic tees, athletic sets, ripped jeans.
• Aim for neat, clean, and fitted rather than tight.

If you only do one thing: swap casual shoes for a more polished pair (loafers, boots, simple heels). It changes the whole message of the outfit.

The 3-part formula that always works

Think of upscale casual as:

1) One elevated anchor

Pick one:

• Blazer or structured jacket
• Tailored trousers or a clean dark jean
• A midi dress or jumpsuit
• A polished knit (merino, cashmere-blend, or a fine rib)

This is the “upscale” part.

2) One relaxed element

Pick one:

• T-shirt (plain, good neckline, no graphics)
• Knit top
• Dark denim
• Minimal sneaker (only if the rest is sharp)

This is the “casual” part.

3) A clean finish

This is where most people win or lose the dress code:

• Shoes that look intentional
• Bag that isn’t beat up
• Smooth hair, clean nails, minimal lint

What “upscale casual” usually means in real life

Different sources describe “smart casual” and “business casual” as adjacent dress codes: polished, neat, and flexible, with smart casual typically being more relaxed than business casual.
A good mental map:

• If it’s a nicer restaurant: “upscale casual” often means no beachwear, no overly casual tops, and no sloppy footwear.
• If it’s an event (rooftop, birthday dinner, gallery, date night): you can lean a bit more fashion, but you still want polish.

This won’t work if the venue is actually enforcing a stricter policy (some places quietly mean “jacket preferred” even if they don’t say it). In that case, go one notch dressier than you think.

Outfit ideas that hit the code without overthinking

For women

Pick one “base” and one “upgrade”:

Base options

• Midi dress + light jacket
• Tailored trousers + knit top
• Dark jeans + blazer

Upgrades that make it upscale

• Swap flats for loafers or a low heel
• Add a structured bag
• Choose one clean piece of jewelry

A lot of smart casual guidance leans toward dresses, tailored trousers, and jumpsuits as easy wins.

For men

Base options

• Blazer or sport coat + chinos or tailored trousers
• Button-down (or polo knit) + chinos
• Dark, clean denim + blazer (works, but it’s the “risky classic”)

Upgrades that make it upscale

• Leather loafers, derbies, or clean boots
• A proper belt (or intentional no-belt)
• A knit instead of a casual tee

Classic etiquette-style guidance for business casual often includes a blazer/sport coat, collared shirt, slacks/khakis, and loafers.

The “what not to wear” list (the stuff that gets you side-eyed)

Public-facing guides to smart casual consistently warn off the extremes: overly casual items (graphic tees, flip-flops) and overly formal pieces (full black tie energy).

Skip:

• Ripped or heavily distressed jeans
• Athletic shoes that look like you came from the gym
• Flip-flops, slides, or beach sandals
• Loud graphics, slogan tees
• Anything wrinkled, stained, or visibly worn out

Shoes: the easiest “decoder ring”

If you’re unsure, decide based on shoes first:

• Safest: loafers, ankle boots, simple heels, dressy flats
• Usually fine: clean leather sneakers (minimal, no neon, no running soles)
• Often wrong: athletic trainers, flip-flops, worn canvas shoes

Clear trade-off with no perfect solution: sneakers are more comfortable, but the more “performance” they look, the more they drag the outfit back down into regular casual.

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How to adjust for time and setting

Daytime upscale casual

• Lighter colors, softer structure
• Flats or loafers
• Less shine, less “night out”

Nighttime upscale casual

• Darker palette, sharper silhouettes
• A slightly dressier shoe
• One statement detail (coat, bag, earring, watch)

A lot of the confusion comes from people dressing for the wrong “lighting.” Daytime polish is different from nighttime polish.

Accessories and grooming (small moves, big impact)

This is optional. Skip it if you already have a simple routine that works.

• Keep jewelry simple and intentional (one focus point)
• Choose a bag that holds its shape
• Do a 10-second lint check, especially on dark clothes

Common mistakes (and the fixes)

1. You go “casual casual” instead of “polished casual.”
   Fix: add structure (jacket, trouser, knit).
2. Your jeans are doing too much.
   Fix: dark wash, no distressing. Jeans are widely seen as acceptable by many people for smart casual, but ripped jeans are not.
3. Your shoes are too relaxed.
   Fix: swap to loafers/boots/heels.
4. You look overdressed for the room.
   Fix: keep the silhouette clean, reduce shine, drop the “event” accessories.

FAQ

Is “upscale casual” the same as “smart casual”?

Often, yes in practice. Many guides position smart casual as polished but relaxed, sitting near business casual.

Can you wear jeans?

Sometimes. Dark wash, no rips, good fit is the safest version, but denim can be divisive depending on venue.

Can you wear sneakers?

Sometimes, if they’re minimal and the rest of your outfit is structured. If you’re unsure, choose loafers or boots.

Do you need a blazer?

Not always, but it’s the easiest shortcut. A blazer with the right pants and shoes is a common smart-casual “uniform.”

What’s the safest one-outfit answer?

• Women: midi dress + jacket + loafers/heels
• Men: blazer + chinos + button-down + loafers
  These align with mainstream etiquette guidance around smart/business casual.