Casual Preppy is the New Cool: Spring/Summer Style Guide

Streetwear’s not dead, but it’s definitely letting someone else talk for a second. The loud graphics, mega logos and oversized fits are cooling off, and taking their place is something a little more subtle and sophisticated.

Enter the era of casual preppy.

Think collared shirts, clean trousers/shorts, crew socks with loafers, and matching sets that say “I trade stocks and crypto and have good taste in gelato.” It’s a mix between millennials and Gen-Z, a mix of looking professional and successful, with an effortless style that’s more comfort focused and basic. The “Yeah, I work from home, but still stay presentable and on trend when running errands.”

What’s Considered a Casual Preppy Style?

It’s the kind of style that looks a bit classier and expensive without being too uptight and nerdy. Casual preppy style is a mix of classic, collegiate staples—button-ups, chinos, polos, crew neck sweaters—refreshed with a modern, relaxed fit and chill, subtle color palettes. You’ll see lightweight layers, clean slacks, and subtle prints like gingham or stripes.

The vibe is smart but still minimal and casual. Casual preppy isn’t trying to look uber professional or try to impress with labels. It’s about looking well-off and well-dressed, while still being cool and casual enough to go to any dive bar or back yard BBQ.

What You’ll See Everywhere This Season (Spring/Summer 2025)

CLASSIC POLOS AND BUTTON-UPS

While polos and button-ups never really go out of style, they are back in style, not only as officewear, but in general trends for men. This season’s polos are fitted but not tight, often with soft collars, ribbed hems, and a slightly vintage vibe. Think tennis club energy, but for brunch or a rooftop hang.

Stick to lightweight fabrics like cotton-linen blends with one solid color or subtle prints and textured fabrics that add a bit of quality and style to a simple outfit. Untucked and casual is the look, unless the occasion is more formal. For chillier days, crew neck sweaters in classic neutral colors can be worn or casually tied around the shoulders.

Go-to shades:
Pastel colors and lighter shades are the go-to this season. White, cream, faded varsity blues and greens, sage, buttery yellow, rust, or soft gray. All easy to pair with neutral bottoms and classic sneakers or loafers. Avoid wearing all dark pieces or loud colors like neons and graphics.

TROUSERS / SHORTS

Trousers and cargo shorts are essentials for the classic preppy looks. Wide leg style trousers are in style this season as well as longer shorts. Fitted pants (not skinny) still work well, especially in work environments where wide leg pants may be seen as professional. Neutral colors make it easy to mix and match with almost all of your tops, and you probably already have a few pairs in your closet.

Best colors: Traditional khaki, olive, cream, stone, navy.
What to pair them with: Polos, button-up shirts, or a relaxed knit tee. Works well with all shoes, slides, sneakers, loafers, to dress shoes.

MATCHING COLOR SETS

Matching color top and bottom outfits are everywhere this season. They’re clean, trendy, and take the guess work out of trying to match when getting dressed. Go for the same color sets or a few shades off. Monochrome sets in lightweight fabrics give off that casual summer preppy energy without being too dressed down. Throw on with some loafers or clean sneakers and you’re good to go to almost any function.

The move: Go for linen or lightweight cotton. Keep the color soft: mint, dusty pink, butter yellow. If you want to edge it up, go monochrome with olive or beige and layer a silver chain.

Casual Prep Starter Pack: Outfit Ideas

The “Cool Professor” Look

For more professional environments, a light blue gingham shirt pairs well with olive cargos and crisp white sneakers or loafers. Add a messenger bag and tortoiseshell sunglasses to pull it together. It’s simple, most likely already in your closet, and a great everyday outfit for summer that works on campus, in the city, or anywhere in between.

Shirt – Manwan Short Sleeve Plaid Casual Button Down
Cargo Pants – Wrangler Authentics Men’s Relaxed Fit Stretch Cargo Pant
Bag – NEWHEY Vintage Genuine Leather Messenger Bag/Briefcase

The “Coffee Date Flex”

For a casual first date or meeting, a button-up (buttoned up or unbuttoned with a tank top under), loose-fit trousers and clean loafers works perfectly in balancing casual and formal. Add a few subtle accessories, like a leather-strap watch or modest jewelry, to dress it up a bit. It’s relaxed but still looks like you made some effort, the perfect vibe for a casual first date.

Shirt – COOFANDY Mens Casual Button Down
Trousers – HOTake Men’s Linen Dress Pants
Loafers – Tommy Hilfiger Men’s Attle Driving Style Loafer

The “Off-Duty Finance Bro” Fit

Clean, name brand polo, relaxed khaki shorts or trousers, and brown leather slides. Tie a sweater around your shoulders if you really want to prep it out. Tack on a few more accessories, designer watch and sunglasses, and a leather briefcase/bag with a laptop you’re not opening. It’s relaxed but still high-value, like you just closed a deal before 10 AM and you’re now off to brunch.

Polo shirt – Nautica Classic Short Sleeve Deck Polo Shirt
Shorts – Dockers Men’s Straight Fit Supreme Flex Ultimate 9.5″ Shorts
Slide Sandals – UGG Men’s Seaside Ii Slide Sandal

The “Office to Rooftop Party” Outfit

For late nights out, go for a fitted button-down shirt or textured short sleeve polo paired with pleated, relaxed fit trousers. Loafers keep it sleek without being to dressy and formal. Add a flashy watch and a couple subtle accessories, and do something with your hair- gel, blow dry -anything. It’s smart, relaxed, and you don’t need to go home to change when work turns into drinks.

Shirt – PJ PAUL JONES Textured Knit Polo Shirt
Loafers – Bruno Marc Men’s Dress Loafers Slip On Casual Driving Loafer

The “Lazy Day But Still Trendy” Uniform

For casual meet ups with friends or if you’re just out and about running errands, a light polo or unbuttoned button-up paired with medium length shorts or breezy draw string pants, crew socks, and comfy slides or sneakers is all you need. Add a hat a bucket hat or a baseball cap if you can’t be bothered with your hair, and a cross-body bag if you’re looking to accessorize. The effortlessness is what makes it ‘cool’, and pretty much the uniform for Gen-Z.

Shorts – NY Threads Athletic Shorts with Pockets
Button-up – Dubinik Mens Short Sleeve Button Down Shirt
Clogs – Project Cloud Mens Clogs – Full Grain Genuine Leather

Accessories That Hit

In Casual Preppy style lane, accessories reflect more of utility, as loud, fancy pieces go against the effortless vibe of it all. Of course, it only should appear that way, as you’re always putting thought behind your overall appeared.

Stick To:

Glasses/Sunglasses – Large wire frames for everyday wearer, and dark shades for sunny days.
Leather crossbody or mini satchel – Practical and stylish, shows attention to details.
Retro watches – Digital or analog. Bonus points if it looks like you found it in your dad’s drawer.
Minimalist Jewelry – A slim chain, a signet ring, or a simple bracelet. Just enough bling to subtly catch the light.
Crew socks + loafers or runners – Yeah, it’s intentional. Nerdy is the vibe.
A book you won’t finish – Optional but on brand.

Colors to Play With

Colors often seen in this season’s casual prep style keep it light and low-key, but aren’t afraid to try a range of shades. The palette leans into tones that feel academic, nostalgic, or quietly luxe. You’ll see more subtle faded shades of classic colors reminiscent of a school campus rather than bold, bright neon colors or anything too flashy. These shades are all over runways right now:

Soft pastels: Mint, butter yellow, and lavender all give off a scholarly coolness. They pair well with white, cream, or khaki for easy contrast.
Muted classics: Navy, olive, stone, and cream are your essentials. They feel clean, grounded, and timeless—like you know how to dress without needing attention.
Pops of color: Sky blue, varsity greens/blues, and rust can elevate a basic outfit. Think of them like the color version of a clever one-liner—well-placed, not overdone.
Washed brights: Faded red or chalky orange can work when the rest of the look stays relaxed. These are great for graphic tees, retro polos, or socks with a personality.

If it looks like it belongs in a summer classroom or an upscale café, you’re doing it right.