Cowboy in the City feat. Alex Crawford

March 7th, 2014

Alex has really been coming into his own.

He’s perfected the ‘Texas Rancher meets menswear Art Director’ aesthetic. His last post on frayed denim was awesome, so we had him take the reins on this one too.

“I’ve always had a thing for workwear and southern inspired dress. In the past year or so I’ve been getting more and more comfortable in those styles, but up until recently I didn’t own a pair cowboy boots. I mentioned this to my dad when I was in Houston over the summer and he pulled this beautiful pair of custom boots out of the back of his closet. Since then I’ve been wearing them almost exclusively.

So when it came time to pack for fashion week in New York, I figured I would just plan my outfits around the boots. I always dress a bit over the top for NYFW anyway, so I saw this as an opportunity to test their versatility. On my last day in Texas my dad pulled out this amazing turquoise bolo tie and said; ‘you can’t have a pair of boots without a bolo’.”

    1. Cold City Cowboy


    “The last five months in LA have softened my skin more than I thought it would. On our first day in NYC staying warm was priority number one. White cut-off jeans with cowboy boots is already a statement, so I just bundled up from there.”


    “I know that Dan has featured this beefy Yokoo scarf before, but I just have to mention it. The weight and warmth is incredible – it can replace a heavy parka. It also garnered a fair share of compliments at shows.”


    “One of the best things about inheriting a pair of well-made old boots is that you don’t have to go through the process of breaking them in. I brought two other pairs of boots on the trip, but ended up wearing these everyday. They were just so warm and comfortable (with thick wool socks).”


    If you’re looking for a pair of versatile cowboy boots, look for something simple, medium brown, and understated. Avoid crazy colors, two-tones, contrast stitching, extra pointy toes, aggressive animal skins, any embroidered logos/bedazzling, etc. Think like a real cowboy, not as an urban fashion cowboy. Authenticity is key.


    • Brown Felt Hat bought from a homeless man in San Francisco
    • Oatmeal hand-knit scarf by Yokoo Scarves
    • Vintage Bolo Tie
    • Navy Henley by Old Navy
    • Chambray Pop Over Shirt by H&M
    • Navy Peacoat by Levi’s
    • Denim Shirt by H&M
    • White 511 Jeans by Levi’s
    • Custom Vintage Brown Leather Cowboy boots

    2. Texas Two-Piece


    “I knew from the start that I wanted to wear these boots with my black MAB peak lapel suit. You’ll never see me mix black and brown leathers, but I’ll mix black and brown fabrics all day.

    I raided Dan’s closet for this moleskin overcoat from Banana Republic. Funny how the size small fits us both… When I went to the Houston Rodeo as a kid, the older cowboys always wore a duster over their suit to keep it from getting dirty. I don’t have a duster anymore, but the 3/4 length and rugged texture of this trim topcoat was a perfect replacement.”


    “I really love the way a bolo tie looks when fastened all the way up. I’ve been wearing this one loose and casual, but there’s something sharp about replacing a traditional necktie with a bolo. Then again, I grew up in a culture full of bolo wearing men, so my perspective may be a bit southernly skewed.”


    “My dad gave me sh-t for the length of my trousers when he saw this photo. But, cowboy boots or no cowboy boots, I’ve never liked the way slacks look pooled around a man’s ankles. I’ll stick with no-break for now.”


    • Beige Stratoliner Hat by Stetson
    • White French Cuff Shirt
    • Vintage Bolo Tie
    • Brown moleskin topcoat by Banana Republic
    • Custom Vintage Brown Leather Cowboy boots

    3. Western Textures


    “Or course I had to go full-western for one of the looks, NYC or not.

    I could see a cowboy saddling-up his horse on a cold winter day in this outfit.”


    “Stealing from Dan’s closet again here; this vintage cowichan sweater was perfect for this western look. I spend most of my money on camera equipment – and he gets plenty of free swag – so we share the love.”


    “I really love the mix of fabric textures in this look. Fur felt, waxed cotton, corduroy, rugged wool, broken-in denim, old beat-up leather…all the good stuff.”


    • Beige Stratoliner Hat by Stetson
    • Vintage Bolo Tie
    • Navy Henley by Old Navy
    • Denim Shirt by H&M
    • Vintage chunky “cowichan” zip shawl cardigan
    • Green Waxed Cotton Barbour Beaufort Jacket
    • Blue Jeans by J.Crew
    • Custom Vintage Brown Leather Cowboy boots


    Thanks, as always, for reading.

    Yours in style,

    Dan Trepanier

    • Arrowsmithshoes

      Thanks for sharing your experience with us about cowboy boots.Here you
      have present awesome pictures to provide the idea about the fashion of
      modern era.

    • Stuart

      Alex, I’d like to think that we’re long lost fashion brothers. Always love the looks.

    • Koko

      Alex. The short torn jean look over a western boot reminds me of the ubitquitous window shutter that doesn’t match the window. Sitting in a saddle with those jeans and boots would be a horrible thing to contemplate.

      • Alex Crawford

        I think my first mistake in that scenario would be riding in white pants! My jeans are always filthy after riding.

    • ChrisD

      The first look is perfect. That “tie” falls perfectly among the colors and textures of the layers you’ve got going on.

      Did it feel/look strange to you wearing suit pants over those boots? When wearing such thick leather boots I’d feel more comfortable with a more rigid pant leg. Not sure why, just seems off.

      You only get a few of those gems where a family member pulls something like that out of their closet for you :) It seems like you get many of these experiences! Jealous… Enjoy

      • Alex Crawford

        I am very lucky that my father was so cool, haha.

    • John B

      Alex looks amazing here. Definitely not something most guys would wear (including myself), which makes it even better.

    • TK

      Good post fellas,just not a fan of the scarf.I get it’s warm but when you get to your destination,then what?? Where can you possibly store that thing? No need for a scarf that size! C’mon son…

      • Dan Trepanier

        Don’t knock it till you try it. I stand by this thing 100%…and I have a few scarves.

        • TK

          So where do you put it when you get to your destination? It’s equivalent to wearing a blanket out of the house,sure it’s warm but not necessary! Not for me,do you though!

          • Dan Trepanier

            With my coat. Sometimes stuffed in the sleeve.

    • TO

      Killer post by Alex! No. 2 is the best I’ve seen someone wear a bolo ‘thus far’, because we know it is building steam as a big trend. I can’t get over how good the black suit goes with the boots and western tie. Solid looks from AC!!

    • Matt

      How tall us Alex?

      • Dan Trepanier


    • Alan

      A timely post. I’ve been working on getting my style associates into cowboy boots. I love mine. But I’ll admit… They’ve got a contrast stitched welt and inlays on the shafts. They’re far from urban cowboy, though. They’re straight out of M.L. Leddy’s in the Fort Worth stockyards, and they’re awesome.

    • Wes

      Blame it all on his roots, he showed up in boots.


      • Alex Crawford

        And ruined your black tie affair.

    • Matt Johnson

      As your hair grows, so does your sense of style. Great looks. Even better flow.

      • Dan Trepanier

        From the President of the Flow Appreciation Society himself. Hope all is well Matty! Missing you out here in your neck of the woods.

        • Matt Johnson

          Missin you too brotha! Huge congrats on the engagement!!

    • Khalid

      That brown moleskin coat in size small is an amazing fit. It fits 6’2″ Dan, my 5’1″ father (with sleeves shortened), 5’7″ Alex, 5’10” me, and lanky Wes as well, with the proportions and pocket placement always appearing just right.

      • TO


      • Dan Trepanier

        It’s true. And kind of a mystery. I think it’s mostly due to the rigidity of the fabric, which masks ill-fits and keeps a great shape. It’s also a little tight on me (can’t fit a jacket under)…but I like it that way.

    • Randy

      Echoing the positive vibes. Alex clearly knows who he is and isn’t afraid to express it. Also dat bolo. #srslykillinit

    • AK

      Trepanier/Crawford for 2016!

      • Dan Trepanier

        Hahaha our views might be a little extreme

    • cuponoodles

      The excessive finger jewelry is foolish, and the bolo tie is affected and overwrought (although I sadly wish it weren’t). Many of these looks scream “try hard” and inauthentic, despite the claims to the contrary.

      The boots are great though, and the definitely make a statement, especially on the East Coast.

      • Alex Crawford

        I appreciate criticism, but I wish it was more constructive. Why is the jewelry foolish and the bolo tie affected? I’ve seen so many men wear 4+ rings, what about me wearing them is any different? Or do you think anytime a man wears more than just 1 ring it’s foolish?

        The definition of affected is 1. influenced by 2. pretentious or artificial. The bolo is certainly influenced, like I said mostly by my father and other traditional Texans, but how is it pretentious or artificial?

        Sorry, I know I’m coming off as defensive, but I hear these same criticism so much and no one ever really backs them up. I’m just curious, and I do genuinely appreciate your comment!

        • Akil McLeod

          I can definitely appreciate all of these looks Alex. Your style has evolved quite a bit and it is very inspiring to say the least. And speaking as someone who also wears 4 or 5 rings on any given day it is always a pleasure to see someone else rock a fistful of rings. Great job brother!

    • Adam

      Being from Oklahoma, I see more than a fair share of cowboy boots. I don’t own a pair myself, but I am convinced that I WILL buy a pair if I ever come across some that aren’t as gaudy as most of the ones I see on a day-to-day basis. I really love the 1st and 3rd looks, but I just can’t get around the bolo tie in the second look…Just a matter of personal preference.

    • JM

      This is literally how alex needs to dress from now on. No more experimenting, this is his sweet spot.

      • JM

        I also got a few of my grandfathers old bolo ties from my grandma. I’ve been wearing them loose with a chambray shirt and cotton jacket. So I’m all for the bolos

    • Nafi

      Really love how Alex has came into his own style. He has become a huge influence on my personal style. Especially in terms of rugged workwear and classic fedoras.

    • Steñ

      I love everything about this. Seeing people really come intontheir own personal style is very inspiring

    • Ali Naaseh

      Alex has made a lot of progress from the shaved-head, oversized shirt and beat up vans version of himself that first showed up on TSB a few years back. Well done my man

      • Dan Trepanier


      • HL Merkin

        Agreed. Look #1 is absolutely stellar. If you looked at a list that said “cut-off white denim, cowboy boots, huge chunky scarf, oversized bolo tie, and Mandarin-level amounts of rings” it reads like a big gross pile of affectations and trends. This looks natural and excellent.

    • JoeFromTexas

      One of the best all time posts, with look 2 being one of my all time favorites (and look 3 not far behind). By my screen name, you might say I’m a bit biased, well I am. When I kept hearing about the emergence of the bolo tie after Rivers wore it post game, I thought it was a cruel joke. Even growing up in TX, I never really liked bolo ties, but I have to admit it looks pretty perfect in the second look. Brown boots with a black suit, no break hem with boots, breaking all the rules and still looking great.

      There’s this line from a Lyle Lovett song (“That’s right, you’re not from Texas”) about wearing your jeans long when you wear boots. And there’s something about the clean sweep of pant leg to the vamp of a high heeled boot when your hem is longer, but not so long as to pool. I tend to have pants with a full break I wear with cowboy boots, and pants with no break for shoes. But I’m going to have to experiment after this post. By the way, I’m still curious who made those boots. I have one custom pair (that I happen to be wearing today), and the rest of are all used (or I should say vintage) finds, no break-in necessary.

      • Dan Trepanier

        JoeFromTexas, you are absolutely Joe from Texas. Love this comment. Thank you.

    • Robert

      Houston is a shitstain but if Alex Crawford is from there, it can’t possibly be all bad.

      • Alex Crawford

        The armpit of America.

        • JoeFromTexas


          • Alex Crawford

            What?! I love the armpit of America!

        • Harry

          I thought that was NJ

          • Dan Trepanier

            Definitely Jersey. Alex should know that.

            • Jack


    • Wieczorek

      Alex Crawford’s Guide to Building Your Own Wardrobe:
      Step 1: Ask your dad for clothes.
      Step 2: Steal some clothes from a friendly menswear enthusiast (preferably your boss).
      Step 3: Buy some stuff in thrift shops. Make sure there is only one such item in the universe so that only you can rock your amazing clothes.
      Step 4: If you need anything more, ask your dad again or go custom.
      Step 5: Wear everything with confidence and look flawless.

      I love Alex’s style. I always have. He finds great pieces and combines them very originally.

      It seems that he gets a big portion of his clothes form his dad. Those are always nice pieces. I’m wondering, if we could see an editorial featuring the older Crawford. Alex’s dad has got to have outstanding style. Is there a chance of you making a post about him?

      • Ali Naaseh

        Poppa Craw would be cool to see, I’m on board with that.

      • Alex Crawford

        Haha this is surprisingly accurate. I haven’t been able to convince my dad to let me feature him yet. I’m still working on him, so we’ll see. In the mean time here’s a picture of him before his senior prom in 1972. Yes that’s a blue crushed velvet tuxedo.

        • Jeanscuffed

          LOL NOOOO!!!! This is good stuff. All he needs is a pair of long horns on the front of his car and a big ass cowboy hat to complete this look lol. Surprisingly, his suit looks tailored.

        • Wieczorek

          Thanks Alex, now I just want to see him featured even more. And if he does not agree, then well… We have his photo and know where he lives (Houston CAN’T be that big). I’m from Eastern Europe, so it would be wise to make those photos :) Just sayin’

        • Dan Trepanier


    • Jeanscuffed

      Definitely agree with Jorge B. that Alex has really developed his style since I saw him first featured on the site, and I can see him going beyond his current state which is what personal style is all about, transcending. I can’t wait to see of what’s to come for Alex later on in the year. I do have one question though: Alex do you style yourself as in besides men’s workwear (which you were born and bred in so it’s easier to own that look), the other looks outside of men’s traditional workwear. If Dan styles you then kudos to you both of you because you definitely pull off the cowboy look. I ask because I know Dan is more centered around styling whereas you are more centered around photography.

      • Alex Crawford

        Dan definitely helps me out. These three looks I styled myself, although to be totally honest I did send Dan a selfie of the second look just to make sure he thought I wasn’t breaking too many rules. There’s no doubt that Dan has been the biggest influence on my style. Sure I base my aesthetics on the south and on the way my dad used to dress, but if it wasn’t for Dan I wouldn’t be trying any of that. I’d still be wearing t-shirts everyday.

        • Dan Trepanier

          You’re too sweet Alex.

    • cam

      This post is a perfect opportunity to mention something I’ve been thinking about for awhile and then acted on and would like Alex and Dan’s thoughts/opinions. While I don’t wear cowboy boots, I do wear my LL Bean boots and LL Bean Signature ranger boots quite often. I had always worn them with JCrew 484 fit cords/jeans and the ankle would hit at the top of the boot. I had been thinking about buying some RRL slim boutcut jeans to be able to cover the boot. Well I did and I think it looks great. I like the fact that the silhouette is still tailored through the thighs. I know you’ve never really featured bootcut jeans and it seems to be #menswear sacreligion to wear them. With the trend to fuller cuts and the shift from the small ankle openings, your guy’s thoughts?

      • Alex Crawford

        Dan and I were just talking the other day about how we think bootcut jeans are going to come back soon. I’ve been looking for a pair myself. Good on you for rocking them!

    • Massimo

      the look is ok, but I do not like the cuff of these pants, i have seen on several occasions. they seem to short, and just looks unprofessional: cut with scissors and now fraying a bit. Alex’s look always seems to forced and gimmicky, w/ too much layering & accessories imo.

      • Jeanscuffed

        Unprofessional? These looks are built around cowboy boots so I don’t think Alex was going for “professional” in the 1st place.

        • massimo

          unprofessional in terms of cutting the jeans by oneself with a scissors vs. having them done by a professional tailor. I was not referring to professional as in a 9-5 kinda job…durrrr.

          • JoeFromTexas

            I think Alex was going for an “unprofessional” hem on purpose. I’ll go ahead and leave out any patronizing remarks.

          • Jeanscuffed

            I was unclear of which kind of unprofessional you were speaking of. But yes I agree with JoeFromTexas, it’s part of Alex’s personal style to look like that.

    • Tiffany

      Alex, I’m pretty obsessed with you and this is the perfect example of why! You kill your looks in a way that’s completely individual and authentic. Even though I’m a lady, you make me consider pieces I would have overlooked otherwise. Do you, do you.

      • Alex Crawford

        Thanks Tiffany!

    • Jorge B.

      Daaaaaaaamn. Alex, man I LOVE the style you’ve developed. I’m in Houston myself, and I have to say I haven’t seen any cats completely owning Southern influences in the way that you’ve been doing. I’ve never been personally drawn to cowboy boots, but the way you’re incorporating them in these looks is really nudging me to try them. Also, for some reason my mind named look #2 the “Dapper Desperado” haha. Keep that fire coming brother, much love from Houston.

      • Troy

        My sentiments are the same. I wish I had seen this post last week before going to the cook off, I may have pulled out the bolo tie as well. Alex, you have any recommendations for a good tailor here in Houston?

        • JoeFromTexas

          For Troy and Jorge:

          Regarding a tailor in Houston, check out the post:

          If you mean tailoring/alterations, I personally like Duke of Hollywood, in downtown Houston. He does tailoring (i.e. he can make a bespoke suit) and alterations. I’ve only used him for alterations and he does a great job. He’s an interesting character… Also, his shop doubles as a bar, so there’s that.

          @Troy, If you’re in the market for boots, check out the Texas Junk company. As far as I know, they have the biggest selection of used boots in Houston. They’re only open Fridays and Weekends though.

          • Alex Crawford

            I have to check that place out!

            • Sean

              @alex..great post.. I am a fellow h-Towner..cowboy boots are definitely a hidden gem and a major piece in my wardrobe in terms of footwear.. I def agree with your point in regards to selecting a low key boot style with minor detailing…the easiest to style to pull off is the low heel roper with a round toe in brown leather.. All in all great post and keep up the good work.. By the way, were you able to make it back home for the cookoff last weekend?

        • Alex Crawford

          Absolutely, Nick Lopez. Best Tailor in America. We did a post about his bespoke suit shop but he also does tailoring.

      • Alex Crawford

        It’s Rodeo season in Houston right now. If you get a chance to go, even just to the convention and not the rodeo itself, you should. There are some very well dressed cowboys (and cowgirls).