Let’s be honest here: some things are worth the price, while some could be skipped entirely.

Here are some items you should spend a couple extra dollars on, and some others you can skimp on and still come out okay.

Splurge on these if you have the cash

Well-made shoes

You can find “dress shoes” practically anywhere (even Payless has stuff that can pass for decent “dress shoes”, or something that resembles a leather shoe), but there are vast differences between a pair that costs $39.99, $300, and $1600. And yes, there are shoes that cost $1600.

Where do the differences lie? Material (leather vs faux leather), quality of the material, the sole, construction, finishing, and so on. For a decent leather shoe, you’ll want to stick in the $200-$300 range and up. Alternatively, if you’re a slick bargain hunter, you can scour eBay or Style Forum for brands that typically sell models in that price range and buy them at a discount (albeit slightly used in most cases).

L-R: Double Monks, Antonio Maurizi; Burnished Brogue Boots, Harris; Green Double Monks, Bally

I found a pair of used Antonio Maurizi double monk straps in a tan leather for $120 online. These usually retail for $300. Granted, it took a while and I had to be patient in looking for that particular shoe, but if you have that kind of time you can find some great deals online.

I also have a pair of burnished brogue boots by Harris that my lovely girlfriend got me for Christmas. She found them on sale at Barney’s for $275, but their retail is around $600. Deals are plentiful for the patient shopper.

A classic watch

I can’t wait to amass a collection of watches like John Mayer, but until then, I’m setting my sights on an entry-level piece that’s classic and goes with everything.

I appreciate watches more than I do clothes, mostly because it’s a different ball game with a higher barrier to entry. Sure, you can buy a $500 pair of Alden shoes and learn their history, but to know and appreciate (and be able to afford) the mechanics of a tourbillon, for example, is something completely different.

As far as classic, entry-level watches, I’m thinking of pieces like the Cartier Santos, Rolex Air King, IWC Portofino, or the Tag Heuer Monaco. Sure, it’s good to have a Timex as your everyday watch, but as your disposable income grows, look into investing in one of these. Soon it will turn into your everyday watch, and maybe even become an heirloom you pass along to your kid one day. How cool would that be!?

A great suit

Just like shoes, there’s a big difference between a $200 H&M suit and a $6000 Ralph Lauren Purple Label suit. That’s a whole article within itself, but a lot of the differences lie in the construction and fabric alone. If you’re interested in details, check out my friend Antonio’s explanation here on Quora.

The price of the suit isn’t as important as the way it looks on you, so no matter the price, always take it to a tailor.

Assuming I was rolling in dough, however, I wouldn’t mind spending top dollar for a nicely made suit, crafted from some fine wool cashmere, like RLPL. Besides, if you DO have that kind of money, you’ll probably find yourself in a bunch of situations where suiting is necessary. That’s how I picture it, at least.

Save your money; don’t bother spending top dollar

T-shirts, socks, and underwear

I find it a little crazy that Calvin Klein sells ONE pair of boxer briefs for close to $30. Do they last five times longer than the Hanes boxer briefs that I get from Target? As far as I can tell, they’re pretty comparable, save for the branding on the waist band.

Same goes for socks. Paul Smith makes some wonderful socks, but they’re quite pricey. Happy Socks is a great alternative if you don’t want to spend $30 on a singular pair.

Tees as well. I’ve seen T-shirts for $50 and up… for a plain, white tee. Why?

Stick with the basic brands you see at Target, or a 3-pack you find on sale at Macy’s. You don’t need a $50 t-shirt. One brand I do like (that can be pricier than something you’d find at Target) is American Apparel. They have great-fitting tees in super soft jersey cotton.


I’ve mentioned this before, but I’ve never spent more than $50 on a pair of jeans. I stick with dark-wash, unadorned, straight leg denim from Levi’s. If you’re the John Mayer of jeans, and you’re all about the selvedge 20 oz Japanese cone mill blah blah blah that goes for $300+, I can respect that.

For the everyman, however, try a pair of Levi’s 514 and see how you like those.

Bird legs? Levi’s 511. Thighs bigger than your head? Levi’s 501xx Shrink to Fit.

Boom. Done.

So these are my thoughts on what I find acceptable to spend a little more coin on, and what I feel can be skipped.

Agree or disagree? Let’s hear it in the comments below.

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40 Responses

  1. Teresa Baldwin on

    I agree with you on most cases, except for the brands of watches. I worked at a lower end jewellery store for a few years and fell in love with Citizen’s Eco-Drive. http://www.themenswatchreview.com/2010/04/25/citizen-men%E2%80%99s-eco-drive-corso-titanium-watch-review/ is the men’s version of the watch that I’ve now wore for about six years. This is a solid watch that has dealt with me backpacking across Europe, taking care of raccoons, as well as about half a dozen job interviews, if not more. Not a huge price tag, I think they retailed at $475 or so, but fantastic pieces.
    Do you know of a female version of this? 🙂

  2. Real Men Real Style on


    Great article and most I agree with – however I feel it comes down to owning less clothing and seeking quality in everything you buy. Although underwear isn’t seen in public, it does touch your body all day and should be breathable, comfortable, and a bonus if presentable especially when you expect special company.

    Undershirts are a great example – Ribbedtee http://ribbedtee.com/ turned me on to their wares a year ago. Before that I wore the cheap Hanes – since wearing their stretch to fit cottons I can’t wear the Hanes without feeling constricted in the armpits and chest. I will wash laundry before traveling just so I have my 4 Ribbedtee ready for the trip vs. taking one of my dust covered old ones.

    I think I could bring up similar examples for briefs and socks – the point being stop buying disposable crap and instead own clothing that in a small ways makes you feel better. Then you can get to the task of being a better man.



    • Barron on

      I like your point about buying less, avoiding buying disposable crap, and the need to start investing in things that will last. I’ve heard great things about RibbedTee and would love to try them out.

      In my head, I was referring to the other comparable brands you see at mid-level department stores that tend to sell at pretty high price points, but are still of a basic cotton variety with nothing particularly special about them, besides the brand and the price.

      If an undergarment is soft to the touch and super luxurious feeling, I’m often willing to pay that price because I know it will be the layer closest to my body, and it will feel great throughout the day. Spend money on great things and quality items, not just because there’s a brand name on it or because they sell it for a certain price, is my takeaway.

      Thanks for your comment!

  3. SG on


    For the most part I do agree with everything you posted, but my one gripe is your section on denim. Just because you want to wear selvedge denim you don’t have to spend wayward up to $300+ dollars. There are plenty of domestic startup companies that makes selvedge denim right here in the U.S. using material produced here in the U.S. (Ex. Cone Mills in North Carolina). Companies like Imogene+Willie, Baldwin Denim, Railcar Fine Goods, Rogue Territory just to name a few, all of which are based here in the States, use material produced here in the States, and majority, if not all, produced right here. The best part about the products being made right here Stateside is that you’re not spending $300+ but from $140-$200. I would hope that with your relationship with Kate (Who I am financially contributing to because I believe in her foundation behind her company), that you wouldn’t look past domestic small brand companies putting their own products out.

    The quality you pay for selvedge denim, the construction, the process of wearing them into your own personal wash, it’s like your comparison of Payless Shoes to those in the $200-$300 category. How many wears are you going to get out of your Levi’s 514/511/501xx before you have to grab another pair?

    Also, as a John Mayer fan (from his solo stuff to the Trio), I’m partially offended by you saying that he’s obsessed with nothing but Japanese products. If you had known better, you would of understood that he has come out quite a few times in interviews that all the pieces that he wears on a daily routine and during his tours on stage are pieces from any number of his friends in the fashion industry. Never once do you find him in something that you can identify with a brand, with the exception of his extensive watch and, formerly, his shoe collection.

    You spent the whole article differentiating that in each category of clothing, there is a clear difference in quality based on price, yet when it came to denim, you throw it into the same categories as undershirts and underwear? I understand that you said, “I can respect that,” but honestly that just means to me that there is a lack of respect for people who differ to your opinion on that subject. I would hope you would be a little more open-minded the next time you look into selvedge denim.

    And all of this is coming from a 22 year old man who went through the stages of designer denim (Sevens, True Religion, Citizens of Humanity, Hudsons), to this shift of finding denim with no stitching on the pocket (hence why I won’t wear Levi’s even though it is a fashion staple), to the cheaper denims like Uniqlo, to now selvedge denim.


    • Barron on

      Hey SG,

      Thanks so much for your comment. Maybe I shouldn’t have discounted denim so much. I’m just a little turned off by the denim purists who spout off all the time about premium denim while poo-pooing the cheaper stuff. This is just my reaction to that. Also, a lot of my readers can’t always spend $150-$300 on denim, and I’m just confirming that it’s okay.

      That being said, I TOTALLY support and love great products that come out of the good ol’ USA, and like you mentioned, our own brand Fifth&Brannan was conceived and produced right here in San Francisco. I couldn’t possibly ignore home-grown, because we ARE home-grown.

      I don’t mind paying premium prices for stuff that was made here, in fact, I gladly do all the time. But I’m also aware of what I’m purchasing, and I buy things because I want them, not because a group of blogger elites are saying selvedge is the way to go and it’s what all the cool kids are doing. Does that kinda clarify where I’m coming from?

      Lastly, I’m probably a bigger John fan than most (seriously, both for his guitar skills and his off-color, witty humor which is a lot like my own), so I wasn’t slighting him at all, and you misunderstood. I was referring to his love of fine and obscure watch models that he speaks of in the article I linked to, under “A classic watch”. So when I said “John Mayer of jeans”, I meant someone who’s really into denim and knows everything about it.

      You make great points and I’m glad you didn’t let me get away with not giving credit to well-made US denim. I do stick by my guns, however, when I say I personally can’t always afford $200 denim, that a majority of readers probably can’t either, and that there are more affordable alternatives.

      • SG on

        No worries. I used to share your position of never understanding what the whole ordeal was behind selvedge denim, especially all the forum folks riding up on APC everything. But I’ve grown to really like it now and when it comes down to it, I’m rotating about 2-3 pairs of selvedge denim and then a mix of chinos and other sorts. I just feel that as a long term investment, selvedge denim is just a better purchase than a pair of Levi’s even with the price differential. Like I said before, when I can invest in quality, I usually take that route as I’ve made my runs through so many brands with poor construction and quality control, but I am not one of those denim purists who discounts everything other than the denim.

        And yeah, I completely misread your use of John Mayer _____. So my apologies for that. I’m probably right there with you when it comes to being a huge fan of John’s work (Ever so present in my on and off progress of building a replica southpaw version of “The Black One”. From seeing him perform live numerous times to meeting him 5 years back in person, we have many commonalities.

        Keep up the good work though! You continue to put out great material especially for those who are still entering this different realm of clothing and style, and if you can take anything away from our conversation, at least you got one man riled up haha. Cheers, mate!


        P.S. Tell Kate I wish her and you the best of luck and fortune while making the push to get this first collection out!

        • Barron on

          Investing in quality is always good, hands down. If one can afford to buy a quality pair of denim for $200 (and one knows why they’re buying it, and why it’s considered ‘quality’) then by all means, s/he should.

          Another one of my pet peeves is when people buy things but they don’t know why they’re buying them. Usually it’s to follow a crowd, which I think is a terrible reason to buy into things.

          When it comes down to it, I know a majority of my readers aren’t buying $200 denim, or they choose to spend $200 differently (towards a nice pair of shoes, for example) and can’t do both. I’d rather them buy a less expensive pair of denim, at least for now, and buy a nice pair of leather shoes… vs. skimping on the shoes, which is just a bad decision all around.

          Glad we can relate on John’s awesomeness 🙂 And thanks for the well wishes; it’s a little crazy at the 5&B headquarters as we near production, but it’s coming along nicely.

  4. Micah Dickson on

    Great article. I really want to invest in a watch but $3,000 is way out of my price range right now. Any great watches that fall into the $400-$800 range that you would suggest?

    • Barron on

      You can find nice models in that price range, but you’re looking at quartz or hybrid movements instead of automatic. Some models from Seiko like the Spring Drive or the Grand Seiko (http://bit.ly/90agoN) are great if you can find them. I also really like the Victorinox watches like the day/date (http://bit.ly/fi7lwT) and some of the other models, which are way easier to find in stores.

      Start there. Hope that helps!

    • Travis on

      Check out Tissot. Great brand, over 150 years making watches. You can get an automatic in that range and a classic style.

  5. belligero on

    Shoes: definitely worth spending a few bucks. You get what you pay for.
    Watch: get vintage if you want something great for (potentially) not too much expense

    I have to disagree about socks and denim, though. Quality socks make a huge difference in comfort, providing that you get wool (or cashmere/alpaca/etc.). Cheap nasty cotton socks make your feet miserable and stinky.

    There’s also a reason that quality denim costs what it does; it’s far more durable and better looking than the consumer-grade stuff. 

    The best way to get good bang for the buck is to stay away from stuff you see ads for.

    • Barron on

      Certainly, and I agree that in the best case scenario, every piece should be quality, down to your socks and denim. But under the assumption that the man who’s reading this has a limited budget, I’d rather he skimp a bit on, say, a pair of jeans (since he can find a decent-looking pair in the $50 range vs a $275 pair) and splurge on a pair of shoes (because you can’t find a long-lasting, good pair in the $50 range).

      Thanks for your comment!

  6. James on


    If you’re looking for a good deal on comfortable basic t-shirts, try the 3pack of Calvin Klein undershirts (crew or v-neck, whatever your style).  they’re soft and ridiculously comfortable.  If there’s a Norstrom’s Off the Rack (their outlet store), you can find that $30 3-pack-at-Macy’s for $15, but these blow Hanes out of the water.

    good choice on the Levi’s, too, because worn properly, they’ll fit into a variety of social situations- country folk love ’em for the durability while city folk love the style.  I personally am a fan of their Silvertab line, myself (especially on sale).  While other jeans are comfortable and look good, levi’s do that and don’t fall apart after a year (looking at you, DKNY).

    • Barron on

      Hey James,

      Great suggestion with the Calvin tees. This is exactly the type of stuff I’m referring to when I say it’s worth “saving” your money. You can still get a great quality undershirt (in a three pack, nonetheless) for a good price.

      Glad we can agree on the denim as well!

  7. Steve on

    A good place to go for a classic looking watch is LL. Bean. It is $99.00 retail price but it comes with a lifetime warranty (i.e. your watch dies for whatever reason, you send it back in, they give a new one for free). I got mine two years ago and nothing has happened, it just keeps going. Also, the one I got has two sets of canvas wrist bands – one olive and one black. Its cheaper than Timex and they look pretty much identical.

  8. Gabriel on

    This is a really great piece. Especially helpful for a single father and a collage student. Just one question-   
    I’m 5’7 and 110. I’m a tiny little dude. Any suggestions for pants that don’t make me look like a thug or a kid playing dress up.

    • Barron on

      Hey Gabriel,

      What pants have you tried so far, and what kind of denim do you buy? Sounds like you have a slim frame; have you ever tried on Levis 511? They’d probably fit like a straight leg on you. Anything considered “relaxed” or “straight leg” cut for bigger dudes will probably be too large on you.

      • Gabriel on

         thanks for the tip. I hadn’t yet tried the 511, but I’ve considered. Next time I go out I’ll be sure to. 🙂

  9. Luke on

    Great article. One of my goals this upcoming year is to update my wardrobe and dress more classy. My problem is I’m a Big & Tall victim – mostly Hawaiian shirts at my local shop. Got any advice or things that I may not consider (other than get smaller :^/). 

    • Barron on

      How big and/or tall are you? To be honest, even if you’re tall, big, or both, you’d dress the same as any “normally-sized” person.

      It’s all about proportion and fit. Most likely, you’ll need to shop at a brand’s online store to get the big / tall sizes, but they’re definitely available.

      This is all general advice but if you have a specific question, feel free to email me and I’ll do my best to help.

  10. Troy Lilly on

    I totally agree with not spending more than $50 on jeans. I have 5 or 6 pair of 514 Slim Straight jeans, all in difference washes. All my bases are covered, slate blue metallic-esque, smoky gray, casual dark wash, lighter traditional blue and so on.

    • Barron on

      Yeah, I do too. They’re my favorite make and model. When guys are first learning how to buy a good pair of jeans, I always tell them to start with the 514 Levi’s to learn their fit, and they can change models as needed from there.

  11. Anonymous on

    totally agree on the jeans.. Levis 511! Agree on everything actually..I spend on suits, jackets, and shoes.

  12. orlando on

    you can easily get unbranded brand raw denim 15oz for $75

    levis usually run 50-60, no excuse not to own raw denim which will last way longer than levis, for only 15 bucks more .. i love my levis 511 but the quality is low when compared to raw denim

  13. The Crucifier on

    You’re absolutely correct! I’ve often wondered if it’s just me or whether the cost of high-end sox and underwear really made a perceptable difference. I would, however, make one other somewhat qualified addition to the when and when not to save list: It boggles my mind to page through GQ and Esquire, viewing an ensemble of suit, shirt, tie, etc., and to read tha the sliver of a very high-end designer dress shirt goes for $295, $385, $425, and so on. I will admit that a dress shirt with the Nordstrom brand for just under $100 feels softer and more luxurious against one’s skin than a $29.99 dress shirt from Sear’s, Kohl’s, J.C. Penny’s, etc., but how much better is the dress shirt costing WELL over $100? In my opinion, aside from how the fabric feels on the skin, the fit and the construction of the shirt, what is seen from under a suit or sport jacket does not justify the outrageous prices mentioned above for high-end shirts.

  14. Dave Hahn on

    I’m a denim-head that only wears selvedge but I agree that it’s not necessary unless you want to go there and have the disposable income to do so. Also, I’m a casual guy and don’t spend money on blazers or suits so I don’t mind spending the scratch for premium denim since it will be the base of my wardrobe. That being said, I think selvedge fans on the ‘net get stupid about it and take it way too far. BUT the new denim companies are putting out cuts that are pretty tight. Slide into some Baldwin Henley’s and tell me they aren’t awesome…

    • Barron on

      I like that you know what’s important to you and where your money goes. That’s what’s most important in the end. Haven’t checked out the Henley model yet; I’ll do that!

  15. Mustafa on

    I agree with most of it except the t-shirt bit. I am tired of buying cheap t-shirts whose seams twist and shift after a few washes. Just symmetrically align the left side seams and watch it not match the alignment on the right and you will see what I mean. If I don’t get that twisting with the 100$-200$ range t-shirt, it justifies the price.

  16. Pam Lorne on

    I really enjoyed this article. I will show it to my husband. I do not complain when he spends money on his J Adler shoes, but high end undergarments seems senseless!