There are two kinds of summer gear. The stuff that makes the suitcase. And the stuff that never leaves the drawer. This list makes the cut.
The best time to buy the stuff you’re going to live in all summer? Right before summer actually starts, and it’s on sale. That’s the smart shopper’s opportunity of Memorial Day weekend.
It’s getting swim trunks, sneakers, shorts, or easy shirts for less, right before you actually need them. And you don’t need much. Just the right pieces, bought on purpose.
I did the digging. Here’s what’s actually worth grabbing.
→ Scroll to the bottom to see 4 example summer outfit combinations.
My tactical take:
Prioritize the versatile stuff you’ll wear weekly: shorts, swim trunks, sneakers.
These are seasonal basics, not clearance junk. If your size is in stock now, it won’t be in three days.
Remember: a $45 knit polo that looks like it cost $125 is the exact kind of move that separates guys who buy and dress smart from guys who panic-shop at the mall the day before their flight.
J.Crew
6″ Cotton-Nylon Blend Swim Trunk, $46.50 $79.50
Matte finish and clean structure make these look tailored, not touristy. You could wear them to lunch and no one would clock them as swimwear.
Abercrombie & Fitch
Classic Stitch Johnny Collar Sweater Polo, $45 $60
Elevated texture and a structured collar that reads way above its price. This is the one shirt you pack when space is tight.
Amazon
Puma Club 5v5 Sneaker, $45.98 $70
Soft leather, gum sole, and retro lines. Aspects of a Killshot, not a Killshot. Feels like a $100 sneaker disguised as a sub-$50 pickup. See our summer sneaker outfit look book for more inspiration.
Timex Waterbury Classic Dress Watch, $91.38 $115.12
The kind of watch that adds credibility to your entire outfit. Clean dial, real chrono, heritage name.
Reebok Smash Edge Suede Sneaker, $38.50 $65
A sharp court shoe in black and white with just enough retro to feel intentional. Better style than most sneakers twice its price.
Adidas Path Sneaker, $44.96 $65
If your vacation requires lots of walking or you just need something new for the gym, this ultra-clean profile with athletic roots won’t kill your style.
Banana Republic Factory
7″ Lived In Short, $18.75 $60
Classic chino styling with a washed-in feel that makes them easy from day one. This is the basic that slots in anywhere and is under $20.
Textured Resort Shirt, $22.50 $75
Warm-toned stripe and visible slub give this some depth. Looks boutique, feels effortless.
Harbor Linen Wide Leg Pant, $37.50 $100
Fluid silhouette and visual weight without bulk. Makes a simple tee or polo feel styled.
Textured Resort Shirt, $22.50 $75
Tropical without being a costume.
Todd Snyder
Nike Blazer Mid ’77, $66 $105
A true classic, on discount. Minimal color blocking keeps them versatile. If you don’t own these yet, now’s the move. See how I’ve worn them.
Vans Authentic Suede, $69 $98
The suede turns a skate shoe into something grown. Great with everything from denim to linen.
Champion Midweight Sweatshirt, $69 $98
Beefy without being bulky. Details that read premium, has the features I want in a vintage gray sweatshirt. It’s a classic men’s summer style layer that adds structure.
Gap
Open-Stitch Sweater, $21.99 $44.99
Breathable, textured, and visually interesting. Throw it on over a tank or t-shirt and it does the work for you.
Linen-Blend Jogger Shorts, $14.99 $29.99
These are lounge-level comfortable but still sharp enough to leave the house.
J.Crew
7″ Stretch Chino Short, $46.50 $79.50
A summer essential. Slim but wearable, hits mid-thigh, no frills, all utility. Dress it up with a button up, wear it with a loose tank top, whatever you need these will work.
5.5” Linen Cotton Pier Short, $39.50-$52.50 $79.50-$89.50
Shorter, softer, more European. Wear with espadrilles or sandals and you’re suddenly on vacation.
6” Stretch Swim Trunk, $44.50-$52.50 $89.50
More Riviera, less resort. Good enough to wear dry.
Stag Provisions
Birkenstock Boston Suede Clog, $132 $165
The clog that gets worn five times a week because it works every time. Neutral suede that styles with everything. If you hate them, you feel like I’m beating a dead horse. But if you know, you know. The best sandal alternative for summer.
Summer Outfit Idea Examples
A few summer combos, all on sale.
Set for Summer
BBQ? Check. Vacation brunch? Check. Just a normal summer day getting some stuff done? Check.
Summer Hang, Water Involved
You’ve already swam, changed, and you’re still where the action is. The day’s not over, but you’re not headed anywhere fancy. You just want to feel comfortable and still look put-together.
Easy Start, Late Chill
The kind of day where you need layers because it’s cool in the morning and calm at night. You might hit the beach, do a grocery run, or end around a fire. You’re set either way.
Summer @ Golden Hour
Maybe you’ve got an early dinner, a backyard bbq that’s a smidge more upscale than a t-shirt, or pre-dinner drinks at the hotel’s waterside bar. This is casual, intentional, and elevated.
