1 Piece/3 Ways: Cognac Chelsea Boots

April 4th, 2014

I love finding affordable footwear with simple, elegant design.

After writing so much about the value of expensive footwear, I think affordable shoes have gotten a bad rap.  After all, I think one of the best things you can do to make your expensive shoes really last the test of time, is to add a couple pairs to your rotation to give them a break.

Here’s a great example of a fill-in-the-gap pair that I just picked up. They’re the “Remington” leather chelsea boots by Aldo (only $108 with promo code BUY100 – ends Sunday). I have a few nicer pairs of chelsea boots in my line-up, but didn’t have anything in a rich cognac brown; which in my opinion is the sharpest color for Spring footwear. I didn’t want to drop another $400+ on benchmade chelseas, I just wanted something to fill a gap in my rotation, and these have been doing a fantastic job.

Here’s three ways to wear them (although, you can probably wear them with just about anything).

    1. Stick & Move


    I’m off to New York tonight.

    As I’ve mentioned before, I’m an obsessively light packer. I carry the absolute minimum amount of weight in luggage. Any trip under a week is strictly carry-on (and if the trip is longer I’d rather do laundry than lug around a big bag that needs to be checked). The trick is wearing versatile layers on the plane.


    Four days in NYC = everything worn here, plus a tote containing:

    • Green trousers (to match jacket)
    • Houndstooth trousers (to match waistcoat)
    • Khaki trench coat
    • Chambray shirt
    • White oxford shirt
    • Heather grey cardigan

    There are dozens of different outfit combination with just these pieces. (I have no problem wearing the same item twice – or more sometimes – on road trips. A good steam and press goes a long way.)



    2. West Coast Safari


    Living on the Wild Wild West coast has had all kinds of influences on my style. Here for example, unconsciously showing a little southern country/safari vibes. It’s different out West…compared to the sharp lines and professional attitude of NYC.

    The style if as different as the lifestyle. More on that later.


    I found this white linen safari coat in a dusty vintage warehouse where we sometimes dig for treasure. It’s missing the belt, but I think I paid $7 for it. It could probably use a little nip & tuck chez Franklin – but I like it a little sloppy and flowy.

    The henley was an unexpected Christmas gift from Vince. Usually I don’t promote things just because they are mailed to our office…but this cashmere henley is unbelievable soft and probably the most comfortable top I own. They’re known for the hand of their fabrics.



    • Brown felt hat by Stetson (Vintage)
    • Clear frame sunglasses by Vintage
    • White linen safari jacket by Ralph Lauren (Vintage)
    • Cashmere waffle henley by Vince
    • Braided leather belt by Trafalgar
    • Khaki chinos by Polo Ralph Lauren
    • Houndstooth socks by Ralph Lauren
    • “Remington” leather chelsea boots by Aldo

    3. Spring Business


    And of course, a sharp cognac chelsea boot should be smooth enough to keep up with your best Spring suit.

    This navy cotton number (in a beautiful Ariston cotton with slight sheen) is a workhorse for me come Spring/Summer. It’s like having a go-to lightweight blazer and a pair of can’t-fail chinos.


    The baby pink shirt is courtesy of our friend Angel, as you can probably tell by the high-standing power collar.

    The herringbone cashmere tie is also handmade in Italy by Angel Bespoke, and it is an absolutely masterpiece.


    There you have it, three of the endless ways to wear Spring’s hottest boot: the cognac chelsea.



    Thanks, as always, for reading.

    Yours in style,

    Articles of Style


    Photography by Alex Crawford 

    • A H

      The dark green jacket is a color we need to see more of in menswear. Your choice of the boots, the dark denim and other accessories is excellent. I also agree about not overpacking a suitcase.

    • ChrisD

      Dan you are too good at this :)
      The 1-piece-N-ways posts are always great.

      This doesn’t read anything like an ad. Dan is always one to push quality construction over a cheaper price. It’s now become a rule of my own.. but shit if you see a nice looking shoe at Aldo or Zara.. as long as you know what you’re getting and comfortable with the price – do it.

    • T

      I think you should have repeat features – so features are more informational than others. The recent Business post of Squalor to Baller was the most conservative/corporate post I can remember on this blog, and possibly the best post of the last year. I think you should have your popular features repeat regularly.

    • http://unseenflirtspoetry.wordpress.com Unseen Flirtations

      Another home run of a post. Or slam dunk? Touchdown? I don’t know, I’m British.

      Anyway, that navy suit is the missing Holy Grail of my wardrobe. I know one shouldn’t chase a Holy Grail (Indiana Jones), but there’s something intensely perfect about a go-to navy blazer and infallible chinos.

    • Al Bizzy

      A great example of how a good execution can make me question my own taste. For the longest time, I’ve always said “I hate chelsea boots”. But damn, @tsbmen:disqus, you’re killin it, bruh. I almost want a pair. Almost. lol

      • http://www.TSBmen.com/ Dan Trepanier

        Haha. I’ll get you there. Thx AlBizzy

    • MN

      The boots are honestly pretty good – Aldo nonwithstanding.

      It’s too bad about the elastic sides though… if they were zips I would probably cop.

      • http://www.TSBmen.com/ Dan Trepanier

        Hmmm…If they were zips I would definitely not cop. The elastic side slip-on is a staple of the chelsea boot style.

    • d4nimal

      It’s so hard for me to come to grips with this for the simple reason that if you wait and skulk around, you can usually find something better for around the same price. You can quite often get 2nds pairs (usually a small mark or scratch – sometimes you can’t even tell what was ever wrong with it) of Allen Edmonds for $125 shipped (or less) a couple times a year. The difference in quality may not be readily apparent in full body shots, but up close they’re universes away in terms of quality at literally every point.

      I feel like Aldo shoes have a sort of prop feel to them, like when you go into a home depot and all the TVs on stands are actually made of cardboard. I know that sounds harsh, because from afar they look good. Point being, though, that if you look hard enough and have some patience, the price difference between Aldo and higher quality brands is much smaller than you think it is, therefore negating any reason to go into an Aldo store unless you couldn’t find the style you wanted (which is a fair argument).

      On another note, loving the style looks, Dan. Looking forward in particular to your suit breakdowns. While you’re in NYC, ever thought about visiting Martin Greenfield? Would love to see your take on such a historic menswear figure and giant of the tailored world.

    • Shawn

      Love the first look Dan, that green jacket of yours make me green with envy (pun intended). I’m impressed with how the boots look, no one could tell their cheap-ness when paired with fits like those!

      • http://www.TSBmen.com/ Dan Trepanier

        Hit ’em high, hit ’em low.

    • MS

      Really, really impressed with how quality those boots look, Dan. And great post, great styling. I don’t know, man, you’ve really been stirring the pot lately but I think this post is class TSB. All the best.

    • Ellingsen

      That first look! Awesome.

    • Alex R

      That third look absolutely killed it for me. I think the simplicity of the outfit is what drew me in. The color pallet works so well. I love the light pink, khaki and navy combo. And the way the shoes pop off the dark navy was really great too. Angel always hookin it up with his shirts, love the strong collar look. Great post brotha

    • Miguel

      Man, all three looks were on point Dan, a lot of picks for me to try this spring, thanks again.

      • http://www.TSBmen.com/ Dan Trepanier

        Thank you Miguel.

    • cam

      Dan, looking good as always my man. I too try to pack as light as possible when traveling and have really spent some time minimizing my entire wardrobe. With that said, I have to say that telling your readers the “best” way to make their quality shoes last is to buy a few pairs of poor quality shoes is a total sellout move to push a product from Aldo. I understand you have to make a living but this is simply poor and misleading information and I kinda expected more than that from this site. Sorry for the harsh words as you know I’m a longtime reader but feel it needs to be said.

      • http://www.TSBmen.com/ Dan Trepanier

        This post was in no way sponsored by Aldo. Please do not assume we are “selling out” because we are not getting paid here.

        We sometimes work with brands that we like to create content, but 99% of the posts are unsponsored. The way we “make a living” is by creating content that guys genuinely enjoy, interact with, and ultimately can benefit from. The more you come back to the site, the more we get paid. So “selling out” for content, when we have such a loyal daily readership, would be counter productive.

        I genuinely believe that $100 for these boots are a good deal, and an affordable way for most of our readers to boost their Spring wardrobe (which is something guys ask us for Every Day). I’ve actually been buying more affordable shoes lately…the more pairs you have, the less important it is to have goodyear welted footwear. Like I said, the best way to keep your shoes fresh is to have a steady rotation – all former sneakerheads know that.

        Nevertheless, thanks as always for reading!

        • Sergio Arteaga

          To add to this, not everyone can afford to go and spend $200 plus much less $400 on a pair of shoes so for many buying a few cheap pairs is inevitable. I have shoes from the likes of DSW house brands (glued soles), Allen Edmonds, Ralph Lauren by Allen Edmonds and all the way up to Carmina. Would I love to have all Carmina’s in my closet, sure but at $500 a pair it’ll quickly empty my pockets.

          I think this is a great example of demonstrating that a “lesser-quality” shoe can still be dressed up from jeans to a bespoke suit. I’m more impressed with the fact that the leather on those boots still looks great. My experience with Aldo shoes has been less than impressive with the leather wrinkling to a point of not even wanting to wear them.

          • cam

            I was not at all implying that cheap quality shoes are a bad option esp for those who cannot afford quality ones. My entire point is I think it is wrong to suggest the “best” (Dan’s quote) way to make your quality shoes last is to have cheap ones in rotation. That is not at all the “best” way. The best way is to take proper care of your quality shoes and have them re-soled etc. I can purchase one pair of quality shoes and make them last my entire life. Dan has even posted an entire editorial on this. So to suggest that buying cheap shoes from Aldo is the “best” way is simply wrong according to Dan’s own past articles. I will apologize claiming this was a push of an Aldo product but it appeared that way with a hyperlink and a discount code for the product featured. All the best guys.

            • http://www.TSBmen.com/ Dan Trepanier

              “Have cheap ones in your rotation” was not my quote. Simply “add some to your rotation”. If you can afford quality, of course, go for quality. If not, it’s still more important to rotate your kicks to give them a rest. When you have a large collection of footwear, how important is the quality? Maybe they get worn once a month… You don’t need ALL handmade anything. I’ve been hitting ’em high and low since day one on TSBmen.

              As far as the promo code, I was thinking our readers would appreciate a discount. Expect more of this as we develop private TSBmen Reader discounts with some of our favorite brands…


              • cam

                I still think you’re missing my point. I have plenty of cheap pairs of shoes in my rotation (albeit mostly things like Supergas and Bean boots). I still think the “best” (again your quote) to make a pair of Scarpe di Bianco chelsea boots last is to take care of them through polishing, cedar trees and resoling. Not by wasting money on some cheap knock offs. That was my only point. And again, my apologies regarding the discount code etc.

        • MN

          Not entirely true – you get affiliate link commission, I am assuming?

          Ain’t nothing wrong with that anyways. You deserve our support for a good product.

          As regards to glued vs. benchmade vs. handmade, I think it is majorly overblown.

          I bought into the whole “quality” think and have a number of Green/Gaziano/Rider Boot/Carmina/Vass type shoes but – at the end of the day – very few shoes are classic enough that you will wear them long enough for the quality to be apparent.

          Margiela’s chelseas are glued and I have had mine for years… still hold up fine.

          • http://www.TSBmen.com/ Dan Trepanier

            We can make an affiliate commission on any product we feature, so that doesn’t affect which styles we chose to use in the editorials. If I like it and wear it, and think our readers will, I share it. If it’s affordable, we usually get “Thank You” emails from readers…but then, of course, some think its a scam.

            You can’t please everybody.

      • tommyjohn_45

        Ridiculous accusation… As a long time reader, you are aware that Dan provides content that can help even the tightest budget-minded people. I have built an outstanding shoe collection that consists mainly of ‘Call it Spring’ shoes (Aldo’s cheaper cousin). Many pairs I have owned for 4+ years and they still hold up extremely well and I get compliments daily. Many literally cost me less than $30!!!! If I were a blogger, and had an experience like this with CiS, why would I not write about it? As Dan has done with Aldo…

    • Juan

      Look number 2 is probably one of the most solid, best executed looks in TSB history, I just fell in love with it the second I saw it!

      Also, Dan, is that tote you designed still available? Been meaning to get one for like forever!

    • Jeff

      “I’m an obsessively light packer. I carry the absolute minimum amount of weight in luggage”

      Why is this? What steers you away from packing luggage? I’m curious…

      • Jeanscuffed

        So he doesn’t have to go through what Greg Focker went through where the airline lost his luggage lol

        • http://www.TSBmen.com/ Dan Trepanier

          Word. No waiting, no worrying.

      • http://www.TSBmen.com/ Dan Trepanier

        It’s an efficiency thing, and maybe a psychology thing I think.

        I’d much rather carry in my hand only the things that I need to bring, rather than roll around a big luggage full of whatever I want to bring.

        Breeze through the airport, don’t struggle through the airport. Travel should be fun and free-ing.

        • Jeanscuffed

          I have to ask, does your fiance go for the minimalist approach when packing for the same length trip? I figured it would be harder for females (disregarding accessories) to do the same minimal packing.

      • Stephen

        I don’t know about Dan, but I know I vastly prefer being able to get off the plane, and walk right out of the airport, instead of having to mill around for half an hour, waiting for my bag.

        • http://www.TSBmen.com/ Dan Trepanier

          Absolutely agreed.

    • John B

      I really like Chelsea boots, but every time I try them on, something doesn’t feel right. It’s probably the completely empty vamp, which is also why I prefer laced boots.
      The first look is the best for me.