Frugal male fashion: 49 essentials that are always affordable and always in style

Levis, a classic brand with great value.

I love a sale.

But waiting for a sale isn’t the only way to snag a great deal. And sometimes sales downright suck:

  • You can end up getting something because the price looked exciting, not because you need it or actually want it.
  • Things are on sale for a reason, and they’re not always good — could be a weird style, an awkward cut, an unflattering color.
  • A lot of sales are artificial. Stores set fake “retail” prices that nobody actually pays, only to show off a big markdown when they run a sale.

This last one gets on my nerves because it’s such a scam. A product’s value is what people are willing pay for it, not what the seller arbitrarily decides it should be worth. If I tried to sell you a bottle of Coke for $50, saying I marked it down from $500 doesn’t make it a good opportunity.

Like the stock market, the best way to judge something’s value is to know what other people are buying and selling it for. And just like the stock market, there’s value to be found if you ignore the daily noise and focus on the long game.

What does any of this have to do with male fashion? The point is to look for opportunities where something is priced right and has timeless style. Don’t worry about chasing 1-day-only sales, you’ll probably wind up with junk you never really wanted. Do it if you must, but understand that it’s kind of like day trading, a demanding hobby that will probably have negative ROI ultimately.

The point is to look for opportunities where something is priced right and has timeless style.

Just like there are conservative investments that always pay out in the long term, there are frugal male fashion items that are always reliable, affordable, and worth their price. Basically, they’re consistently priced right and you don’t have to hunt for the right time to buy. You won’t cop these at a brag-worthy price. But you won’t overpay for hyped fashion brands or disposable quality. In effect, these are the 401K funds of your wardrobe. Invest wisely.

Try to find brands and items that live in this top-right quadrant. That’s the sweet spot.


Shirts and sweaters
Cotton dress shirt
Flannel shirt
Oxford Cotton Button Down
Polo shirt
White t-shirts

Jeans, pants, and shorts
Birdwell Board Shorts
Levis Jeans

Shoes, boots, and footwear
Chippewa Service Boot
Desert boot
L.L.Bean Boot
Red Wing Iron Ranger
Suede boots
Vans Authentic
Wingtip leather shoes

Socks and footwear accessories
Boot and shoe laces
Darn tough socks
Horsehair shoe brush
No-show socks
Shoe horns
Shoe trees

Suits and blazer
Two piece suit
Navy blazer

Coats, jackets, and outerwear
Wool overcoat
Wool peacoat

Seiko 5
Timex weekender
Orient Ray II

Amazon Basics suitcase
Baseball hat
Cashmere scarf
Leather gloves
Lint roller
Money clip
Passport cover
Sunglasses: beaters
Sunglasses: nice
Tie clip
Watch repair kit
Weekender bag
White pocket square
Wooden hangers

Shirts and sweaters

1. Cotton dress shirt

A simple cotton dress shirt in solid white or light blue is timeless and versatile. Get a few and keep them well cared for and you’ll be able to rotate them for years.

Amazon Essentials Solid Dress Shirt
Buttoned Down Solid Dress Shirt from Amazon

2. Flannel shirt

Might be no pattern more iconic than flannel. Flannel has been a American icon pattern for generations. It conjures everything from lumberjacks to sipping bourbon by the campfire, to Kurt Cobain smashing a Stratocaster.

Wrangler Men’s Long Sleeve Plaid Fleece Shirt from Amazon
Woolrich Men’s Trout Run Flannel Shirt from Amazon

3. Oxford Cotton Button Down

Seventy percent of the times you think you need to be wearing a dress shirt, you actually want an oxford cotton button down. These are more casual and a lot more versatile. Wear it buttoned up under a jacket to meet you girlfriend’s parents. When dad wants to shoot pool in the basement later, lose the jacket and roll up the sleeves.

Ralph Lauren Men Solid Sport Oxford Shirt from Amazon
Goodthreads Oxford Shirt from Amazon

4. Polo shirt

It’s a great time to give polo shirts another shot. Because it’s not 2003, brands are making them in great fits. But also because it’s not 2003, they aren’t overpriced mall fashion costumes.

Amazon Essentials Polo Shirt
Lee Uniforms Modern Fit Polo Shirt from Amazon

5. Sweater

A cashmere sweater is a big ask in an article about frugal fashion. But they actually last longer, regulate temperature better, improve over time, and don’t lose their shape like wools and blends. Or just go for a great wool for now.

Amazon Essentials Men’s Crewneck Sweater
Williams Cashmere Men’s Sweater from Amazon

6. White t-shirts

The white t-shirt is an icon and a staple. James Dean, Paul Newman, Brando, the boss, the Fonz. The plain white t-shirt has graced every major cultural moment of the last and current century.

Short-Sleeve Cotton T-Shirt from Amazon
6-Pack Crewneck Undershirts from Amazon

Jeans, pants, and shorts

A few New Yorker Levi’s fans.

7. Birdwell Board Shorts

These shorts are a surf icon.

Birdwell Beach Britches from Amazon
Birdwell Board Shorts, Medium Length from Amazon

8. Chinos

You have to have something to wear to the office.

Men’s 5-Pocket Chino Pant from Amazon
Levi’s 502 Chino from Amazon

9. Levi’s Jeans

Even at full retail, Levi’s offers a great jean for the money. Simply put, nobody at this price point is putting this kind of care and brand development into a denim product.

Levi’s 505s from Amazon
Levi’s 514s from Amazon

Shoes, boots, and footwear

10. Chippewa Service Boot

The secret to making footwear last is having plenty of pairs to rotate through. Hard to go wrong with a rugged pair of Chippewas. They’ll go easily from a night cleaning out the garage to a date at the movies.

6" Rugged Chippewa Boot from Amazon
Original Chippewa Rugged Handcrafted boot from Amazon

11. Desert boot

Sure, you see these shoes on the internet a lot. But for good reason.

Clark’s Bushacre 2 from Amazon
Clark’s Chukka Boot from Amazon

12. L.L.Bean Boot

You’ll pay a little upfront for a Bean boot, but their service and quality are legendary.

6" Bean Boots from L.L. Bean
Duck boot from L.L. Bean

13. Red Wing Iron Ranger

These seem on the steep side, until you realize how long they last.

Iron Ranger 6-Inch Boot from Amazon
Heritage Iron Ranger Work Boot from Amazon

14. Suede boots

Suede is way more durable and efficient of a material than it gets credit for. Like a lot of natural products, these develop a handsome patina and actually get better looking over time.

Bushacre 2 Suede Chukka Boot from Amazon
Clark’s Chelsea boot from Amazon

15. Vans Authentic

The Vans Authentic belong in a museum about youth in America. Or at least California.

Vans Adult Authentic Core Classics from Amazon
Vans Unisex Authentic True White from Amazon

16. Wingtip leather shoes

In a conservative business setting, Wingtips are pretty casual. But for most of us who aren’t bankers, they’re formal enough for almost any occasion. And still casual enough for an outdoor party with jeans.

Johnston & Murphy Oxford from Amazon
Allen Edmonds Strand Cap Toe from Amazon

Socks and footwear accessories

17. Boot and shoe laces

Upgrading shoe laces is an easy way to bring some new life to old kicks.

Round Heavy Duty Boot Laces from Amazon
Waxed Cotton Oxford Shoelaces from Amazon

18. Darn tough socks

Darn tough socks come with a legendary return policy. Consider all the socks you buy and burn out in a given year. Now imagine those socks lasted for years and got replaced for free when they wear out.

Darn Tough Merino Wool Micro Crew Sock from Amazon
Darn Tough Full Cushion Socks from Amazon

19. Horsehair shoe brush

Leather shoes and boots pick up all sorts of dirt and dust on their travels. Give a quick brush with a horsehair brush after each wear and prolong their life.

Kiwi 100% Horsehair Shine Brush from Amazon
7" Horsehair Shoe Brush from Amazon

20. No-show socks

Cool sock-less look without the uncool smelly shoes thing.

Saucony Men’s 6 Pack No-Show Socks from Amazon
M&Z Mens Cotton Low Cut No Show from Amazon

21. Shoe horns

Shoe horns very inexpensive and save the back of your good shoes and boots and they’ll last forever. Plus they look kind of cool.

Stainless Steel Shoe Horn with Leather Strap from Amazon
18-Inch Stainless Steel Shoe Horn from Amazon

22. Shoe trees

These shouldn’t even be optional, really. Shoe trees are a necessity if you’d like your leather shoes to last. Leather shoes last a lot longer when they live in these between wears.

Woodlore Men’s Shoe Tree Pair from Amazon
Product name from Amazon

Suits and blazers

23. Two piece suit

Spending less than $500 on a suit isn’t going to get you anything that will last a lifetime. But if you only need a suit a few times a year, these are a great option. Build confidence, get that raise, and upgrade when you’re ready.

Ben Sherman Two Button Plaid Suit from Amazon
Tommy Hilfiger Nathan Suit from Amazon

24. Navy blazer

A navy blazer is frugal because it’s so darn versatile. These will never be heirlooms at this price point. But consider wearing a blazer is like driving a race car, you don’t want to learn in the best.

Eddie Bauer Men’s Voyager 2.0 Travel Blazer from Amazon
U.S. Polo Assn. Sport Coat from Amazon

25. Tuxedo

Just owning a tuxedo, regardless of its pedigree, will surprise and delight people.

J.Crew Peak-lapel Tuxedo

Coats, jackets, and outerwear

26. Wool overcoat

These coats create a classic silhouette that won’t ever go out of style.

Men’s Single Breasted Wool Walker Coat from Amazon
Kenneth Cole Topcoat from Amazon

27. Wool peacoat

If an overcoat feels a little too muted, try a peacoat. They’re just a little more fun.

Nautica Wool Peacoat from Amazon
Levi’s Wool-Blend Peacoat from Amazon


28. Seiko 5

This might be the best deal on this whole list. To get a Japanese automatic watch for under $100 is insane. On top of that, you’re getting one from a pioneering brand that revolutionized the industry. You’ll get nods from guys in Pateks.

Seiko 5 SNK809 from Amazon
Seiko 5 SNZF17 from Amazon

29. Timex weekender

Timex is on tear this century. If you’re new to watches, start with a weekender. A solid, simple, dependable quartz. You’ll get nods from guys in Seikos.

Timex Weekender from Amazon
Timex Weekender Chrono from Amazon

30. Orient Ray II

Another incredible automatic watch at a great price. You could easily pay 5 times this for something comparable.

Orient Ray II from Amazon
Orient Mako II from Amazon


31. Amazon Basics suitcase

Cheap suitcases are like cheap bikes, totally fine if you don’t use them a lot. Unless you travel for work, go for a handsome suitcase like this.

AmazonBasics Softside Spinner Luggage
AmazonBasics Hardside Spinner Luggage

32. Baseball hat

Every kid’s a baseball hat kid. Then guys get older and decide to go one of two ways: never hat or always hat. Try a solid color, non-branded hat. Great for taking the dog to the park or Sunday morning walks to get coffee.

Cotton dad hat from Amazon
Top level baseball cap from Amazon

33. Belt

A $20 like these will last the rest of your life and a $10 belt will probably fall apart in a year and cost you another $10 the next year, and again the year after that and … you get the idea.

Dockers leather casual belt from Amazon
Timberland Men’s Classic Leather Jean Belt from Amazon

34. Cashmere scarf

These are great prices for the kind of scarf you could easily find for many times this much.

Winter Cashmere Scarf from Amazon
Cashmere scarf from Amazon

35. Iron

When you iron a shirt, you care more about it. When you care more about it, you’re more careful when you wear it. When you’re more careful, it lasts longer. You save money.

Sunbeam Steam Master from Amazon
BLACK+DECKER Professional Steam Iron from Amazon

36. Leather gloves

These look great with those coats I recommended.

Pierre Cardin Leather Glove from Amazon
Carhartt Men’s Insulated Full Grain Leather Driver Work Glove from Amazon

37. Lint roller

Great for cleaning up a thrift store find.

Flint Retractable Lint Roller from Amazon
Scotch-Brite Lint Roller Combo Pack from Amazon

38. Money clip

Money clips don’t have to be dorky, they’re great for going out in a suit when pockets can make your wallet bulge out.

Stainless steel money clip from Amazon
Tan leather money clip from Amazon

39. Passport cover

Passports expire after 10 years, so you’d have to do a lot of traveling to wear one out. But it can’t hurt to protect it.

Leather passport cover from Amazon
Passport Holder Wallet Cover from Amazon

40. Sunglasses: beaters

Riding a jet ski, backflipping into the pools, rounding third in Fourth of July wiffle ball game. The most fun times to wear sunglasses can be the most risky for the actual shades. Get some beaters to compliment the nice pair.

Knockaround Classics from Amazon
Knockaround Premiums from Amazon

41. Sunglasses: nice

Then there’s the nice pair. Driving into the sunset, taking a walk, sitting at an outdoor wedding.

Ray-Ban Wayfarer Sunglasses from Amazon
Ray-Ban Clubmaster Sunglasses from Amazon

42. Tie

Thanks to the Tie Bar, a really great tie can be had for $50. These will last a lifetime and look great doing it.

The Tie Bar Wool Skinny Solid Black Tie from Amazon
The Tie Bar 100% Woven Silk Tie from Amazon

43. Tie clip

The Mad Men look might have worn out its welcome. I still think a simple tie clip always looks good. Stay away from anything too decorative.

Tie Bar Clip from Amazon
Brushed Straight Silver Tie Bar from Amazon

44. Umbrella

Companies want you to think umbrellas are disposable so you keep buying them. That’s silly, you can get one of these quality umbrellas for less than a trip to Chipotle.

Compact travel umbrella from Amazon
J Stick Umbrella Umbrella from Amazon

45. Wallet

Full grain leather gets better over the years. If you’ve only had polyester or “genuine leather” wallets, you’re in for a treat.

Saddleback Leather Co. Full Grain Leather Thin Sleeve Credit Card Wallet from Amazon
Saddleback Leather Co. from Amazon

46. Watch repair kit

For just a couple bucks, you can save thousands in routine watch replacements and repairs.

147 in 1 Watch Repair Kit from Amazon
Watch Repair Tool Kit from Amazon

47. Weekender bag

People think they need to drop big bucks on big suitcases. But the reality is you won’t schlep out that giant bag more than once a decade. What you’ll use ten times a year though, is a duffle bag.

Large Capacity Duffel from Amazon
The North Face Base Camp Duffel from Amazon

48. White pocket square

Forget what I said about Mad Men. Long live the pocket square.

White Silk Pocket Square from Amazon
Woven Silk White Pocket Square from Amazon

49. Wooden hangers

You visit your closet every day. Wooden hangers are the cheapest way to feel like a millionaire.

AmazonBasics Wood Suit Hangers
AmazonBasics Solid Wood Suit Hangers, Cherry

Want something on this list for free?

Every month I select a random subscriber to my newsletter and mail them one of these products. Sign up here and I’ll contact you if you win. Note: The list is still small, you have a pretty good chance ;-)

The fine print: We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.