A blog by "America’s Best Dressed Real Man". Fashion tips, answers to your questions, and all things men’s style
Sunday January 15th 2012



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Comfortable but Not Sloppy – A New Way to Wear Sweats



Hey SB, absolutely love the site. Quick question: do you ever wear sweats anymore? As a former college athlete there must be times when you say “f*ck it, I just want to be comfortable”. Any tips on wearing sweats as a grown-up and not looking like a total slob or fraternity brother?

Thanks, and please keep it coming!


Thanks for the compliments, and good question. You are certainly not the first to inquire about sweats. We’ve been meaning to do a post on the topic.

For the most part, after college I updated my casual wardrobe by trading in most of my team-issued Nike sweats (which were always at least two sizes too big) for some soft denim and chunky sweaters.

From time to time, however, yes there are days when I just want the soft comfort and stretch of fleece – but that doesn’t mean I’m rolling out of bed in head-to-toe Columbia gear.

The trick to not looking sloppy is to invest in proper-fitting sweats with an updated silhouette and mixing them with other pieces from your wardrobe.

Here, some comfortable but not sloppy looks incorporating fleece pieces.

1. “Tailored” Sweat Pants

Same sweat pants, different shape. Slim, tapered, trouser waistband with fly, hemmed, 2″ cuff.

These look similar to flannel trousers, but feel more like pajamas. With a pima cotton t-shirt, cashmere sweater and unlined cotton jacket it doesn’t get much more comfortable than this – while still looking stylish and presentable.

Bonus Tip: These are the same pants that I throw on when I roll out of bed Sunday morning, but because of their fit they can be repurposed for a number of occasions.

…For those long-time followers, you might remember these pants from the very first time that I published a photo of myself on the site (which I used to write anonymously). See the old post on the original version of thestyleblogger.com HERE.

Bonus Tip II: Mixing very casual pieces (like these pants) with sharper ones (like this unstructured jacket) can make for a unique and visually interesting look.

Bonus Tip III: If the inseam is hemmed and the leg is tapered properly you can pair your sweats with more than just sneakers or sandals. Try boots, loafers, or even lace-ups as shown here.

Fleece trousers by Woolrich (size 34). Cotton unlined blazer by Theory (size 40). Plaid cashmere cardigan by Brooks Brothers Black Fleece (size 2). T-Shirt by Ralph Lauren Polo (size M). White suede brogue captoe shoes by Moreschi.

2. The Hoody’s Sexier Cousin

A fleece shawl collar cardigan is more flattering, better for layering, and just as comfortable as the typical fleece hoody that every man owns.

In fact, I find it even more comfortable since you can open or close the front to regulate your body temperature and you don’t have to pull it over your head to take it off.

Bonus Tip: transition your boat shoes to Fall by wearing them with socks…and as we spoke about last post, you don’t have to be shy about it. If you’re looking for more inspiration, take a look at this example of badass hosiery.

Bonus Tip II: In a perfectly edited wardrobe (which I do not have), just about every piece can be interchanged with one another – this includes the waistcoat from a three-piece business suit, boat shoes, and your “Sunday sweats”.

Fleece shawl cardigan by Canterbury of New Zealand (size M). Jeans ad plaid shirt by Polo Ralph Lauren (size 34 and size M custom fit, respectively). Navy waistcoat (part of 3-piece suit) by MAB (bespoke, my own design). Navy/Grey/White striped socks by Paul Smith. Canvas boat shoes by Sperry. Watch by Montblanc.

3. The Knit Blazer

Another great combination of casual and dress: the knit blazer.

Again, it feels no different than a typical hoody, but looks a hell of a lot sharper.

This is a simple t-shirt, jeans and sneakers look – but now you don’t have to go home and change before you meet up with that girl. And if all goes well, she’ll love keeping warm and cozy in it while you cook breakfast ;)

Bonus Tip: It’s not quite heavy outerwear season yet. It’s moderate outerwear + scarf + gloves season.

Piped knit jacket by Rugby (size M). T-shirt by Fruit of the Loom (size M). Scarf by Kennth Cole. Jeans by Polo Ralph Lauren (size 34). Sneakers by Nike. Watch by Montblanc. Grey suede gloves (in jacket pocket) by Thom Browne. Shades (in breast pocket) by Persol.

4. Okay – If You Must Go Full-Sweats

If the situations calls for supreme comfort, you can go full sweats - once in a while.

Again, just keep the items fitted, the silhouette classic, the color palette neutral and the accessories light – as well as the mood.

Bonus Tip: Aside from looking much better, slim sweats have other advantages over looser, baggier ones. They are sleeker to the body so there’s less chance of excess fabric getting in your way or getting snagged on things. Also, the heavy contents of your pockets (wallet, phone, keys, etc) won’t cause them to sag off the body as much.

Bonus Tip II: I keep this outfit on the back of my bedroom door, for those quick 3am runs to the deli.

Piped knit jacket by Rugby (size M). T-shirt by Fruit of the Loom (size M). Fleece trousers by Woolrich (size 34). Tweed cap by Rugby. Sneakers by Converse. 

Thanks, as always, for reading.

Yours in style,



Photography by Jenilee Thorton (yes, we shot this over a year ago – just never got around to posting it)


Leave a Comment



  • Karissa says:

    Love that navy knit blazer :) Great blog!



  • Anthony says:

    Where did you get the sweater vest in the first section of photos? I want one!

  • Ruggine says:

    Functional and very comfortable

  • Min.Q.Cho says:

    Cool & looks so comportable!!

    Can I get the model number of Polo Ralph Lauren Jean?

  • Mountain Dandy says:

    I’ve been wanting a nice knit blazer to wear in the classroom…a little less formal than a regular blazer.

  • COOL SQUARE says:


  • James Schwartz says:

    I just bought a knit blazer prior to reading this post, was very inspired to see the one and only Mr. Trepanier sporting one! Nice job, man!

  • Maurice says:

    Fantastic post! Great job.

  • Ali says:

    Are those the Woolrich Transit Pants? http://www.woolrich.com/woolrich/browse/productDetail.jsp?icProduct=1542&icParent=searchResults&icCategory=&icSort=&icColor=BLK

  • Big Jon says:

    You can wear socks with boat shoes? I thought you weren’t suppose to.

    • George Dunhill says:

      @Big Jon:

      You definitely “can” but probably shouldn’t. I wouldn’t anyways — boat shoes are more casual and, as the name suggests, summertime footwear, which, to me, translates to careless and sock-free. That’s just me, though.

      -Ben T. for George Dunhill

    • Anders says:


  • MikeN says:

    Very interesting stuff here. By the way, ever considered doing a “must-have” list? 5-10 things every guy should have in his wardrobe? It’s the hot thing to do for store websites (popularized by J.Crew i think) but yours, I believe, would have a certain flare to it that the other websites lack. Keep up the great work! -M

  • Aldrin of http://ukaygasm.blogspot.com/ says:

    Thanks for the tips! Veryyy informative! That’s why I love this blog <3 http://ukaygasm.blogspot.com/

  • George Dunhill says:

    Great post and creative use of items that are typically seen as more “lazy” or “overly casual”. Especially love the shawl collared cardigan and can see it making its way into more formal looks & styles.


  • Julian says:

    This time I can’t agree with you Dan. Sweatpants are ALWAYS sloppy. The first and the third look would look so much better with some grey chinos.

    @Every Man’s Closet: Band of Outsiders made a pair a couple seasons ago. But they we’re 400$…

  • A Norwegian says:

    Thanks for great tips! I like the style of this site.


  • Every Man's Closet says:

    Wow, the fleece trousers are a great find! I’d be interested to know what other brands make the same type of pant. Has anyone seen others with a similar cut?

  • Windsorite says:

    Thats the same rugby jackin’ i’ve been rocking and catching so much flack over for the last year Dan! hahaha.

  • AAJR says:

    Glad you posted this. This season I bought two knit blazers, one in grey and one in navy. Let me tell you, they were the best buys this season. They are great for in between seasons. I’ve got a slim sweat pants in grey as well. Love to look put together and extra comfortable. So knit blazers are great!

  • vikflo says:

    Loved the piped knit jacket & the fleece shawl cardigan look. The sweat pant look seemed a reach for me though.

  • Anonymous says:

    I love your blog!

    Congrats on your continued success.

  • Ambyr says:

    That knit blazer is fantastic. I love the white trimming and the ease it has with only 1 botton closure. So chic and comfortable looking.


  • Plain T-Shirt says:

    Good to see some sperrys.

  • HarrisonK says:

    Most of the pictures dont work when clicking on them. Example, the first pictures in looks 2 and 3.

    This is a really great post though. I really like the casualness of each look, they are all perfect for a college campus in DC.

  • balls says:

    Your hair looked a lot cooler in 09.

  • Dorian says:

    Amazing post! However, I’m probably biased since most of the items you are wearing are from my colour palate ;D

  • Khalid says:

    Are the Woolrich pants still available? Can’t find ‘em on the Woolrich website.


  • Tim says:

    Where did you get the socks in the mentioned sb-daily post? They are badass indeed.

    Best wishes

  • Marc says:

    I love your blog!

    Johnny-The jacket is on RL Rugby com and it’s on sale.

  • Johnny says:

    Nice post! Is the piped knit blazer still around anywhere? Really like it

  • Zach says:

    Fantastic post! love the versatility.

    Question, where can you look for sweats like this without spending a fortune?

    • Arron says:

      I got a pair of nice fitting sweats that are fitted at forever 21 for about 23 dollars. Also club monico has some nice ones that usually go on sale.

  • tom says:

    What is your normal chest size and sleeve? I was thinking about picking up that Rugby blazer, but they don’t have measurements on the site. trying to decide between the M and the L.