3 Tips On How To Dress Well And Stay Comfortable

by Barron Cuadro  |  in Style Tips

As men who care about appearance and how well we dress, we concern ourselves with things like fit, quality, and cost.

Not as much attention is paid to comfort, because we assume it sorta just takes care of itself.

Unfortunately, that’s not always the case. When you’re still honing your personal style and taste, you will, to an extent, feel discomfort. But that’s all a part of getting to know what you like and what fits you best.

Along the way, you’ll pick up little tricks that work really well for you and help you feel comfortable both physically and mentally as you try new things.

Today, I want to focus on you being comfortable physically, because I know that once you’re feeling good in your clothing, you’ll ease up and be more confident in your look.

Add these little tactics to your arsenal, so the journey towards better personal style continues without a hitch.

1. Get hot (or cold) easily? Become a master at layering

Smart, strategic layering is a well-dressed man’s version of a Swiss Army Knife.

That’s a weird analogy. What I mean by that is, if you take advantage of layering, you’ll be prepared for any sudden climate change (like when you go from the toasty, warm indoors to the frigid winter weather outdoors).

Layering is simple. Start with your thinnest, most fitted layers closest to your body. And from there, your layers gradually become thicker and looser to accommodate for everything underneath.

So for example:

3 Tips On How To Dress Well And Stay Comfortable
Click image to enlarge in new window || Row 1: Undershirt, Ribbed Tee ($18) | Gingham shirt, Mizzen+Main ($125) | Sweater, S.N.S. Herning ($345) | Parka, Alpha Industries ($200) || Row 2: Boxer brief, Tani ($35) | Long Johns, Uniqlo ($20) | Denim, J.Crew ($125) || Row 3: Socks, Chups ($35) | Boots, Chippewa ($239)

If you’re concerned about clashing or mismatching, stick to mostly neutrals (anything in the white / grey / black family, plus tan, olive green, and navy) and just one large-scale, busy pattern (like plaid), if you’re trying to fit it into your look.

The beauty of strategic layering is that if you do get warm, you can easily shed a layer or two. And when you’re back to braving the elements, it’s easy to throw those layers back on.

So instead of leaving the house in a thin shirt and heavy coat, pad that look with extra layers.

Not only is it a more versatile option when the temperatures change, it’s also more visually interesting and complete (just keep in mind the “rule of three” from the last article).

2. Feel restricted in your shirts? Get one with some give

If you’ve ever worn a dress shirt to work, by the end of the day, aren’t you just dying to take it off and change into something a bit more comfortable?

When I have a sweater and coat over my dress shirt in the winter, that discomfort is only magnified. Sometimes, I’m fine and I can readjust, but often, it’s just something you deal with as a well-dressed dude.

I specifically remember this feeling at my last 9-5 when I had to sit at my desk for hours on end. There’s something about working long hours in clothing that, although I love, can feel a bit restricting at times.

I never really considered other kinds of shirts until recently, one by one, my guy friends started asking me, “Have you tried Mizzen + Main?” I’ve heard about them for years from friends and readers alike, so naturally, I had to give them a try.

The first thing I thought after putting on this dress shirt was, “Why didn’t these shirts exist when I was still going into the office!?”

3 Tips On How To Dress Well And Stay Comfortable
Me, basically, when I first tried on one of these shirts.

Guys, I own many, many dress and sport shirts, and at the end of the day, I can’t wait to get them off and throw on a T-shirt.

This dress shirt from Mizzen + Main is the first one I don’t mind keeping on when I come home. In fact, I could sleep all night in this thing; it’s that freaking comfortable.

Think about your favorite performance gear (like Nike’s Dri-FIT or Adidas’ Climalite)… what do you love about it? Me, it’s all about the fabric’s breathability, stretch, and best of all, its moisture-wicking capabilities.

Mizzen+Main’s Made-in-USA shirts are essentially your favorite workout shirt, disguised as an office-ready dress shirt.

The stretchy performance fabric keeps you comfortable, resists wrinkles, draws moisture away from your body and quickly evaporates, leaving you nice and dry. When’s the last time your 100% cotton dress shirt did all that?

Oh, and if you happen to travel a lot (or you’re just too lazy to iron), these shirts come out of the wash and go straight on the hanger, no dry cleaners or irons needed. Pretty great.

3 Tips On How To Dress Well And Stay Comfortable
Kennedy windowpane, Douglas mini gingham, Fraser multi madras (all Mizzen+Main, $125)

If you’ve ever been in the same position as me, wanting to look sharp while still being as comfortable as possible, with as little fuss as possible? You need to give their shirts a try.

I’ve partnered up with the guys at Mizzen + Main to hook you up with a nice little discount. Just use promo code MAINMAN3 at checkout for $50 off 3 dress shirts. You can shop the collection here.

If you’re looking for something classic, go with the Kennedy windowpane. This will work with suits, but also with denim and a sport coat.

If you’re into something slightly more festive and seasonally appropriate, the Douglas mini gingham or the Fraser madras might be up your alley.

3. Feet hurt? Try a different dress shoe (they’re not all made the same)

If you’re used to wearing sneakers, the first time you throw on a Goodyear-welted dress shoe, you might be a bit uncomfortable. The weight and rigidity takes a bit of getting used to.

My recommendation—assuming you’ve chosen the correct size, and it’s the weight and rigidity you’re not used to—is to wear your shoes until they get comfortable. You’re simply just not used to them.

And while I believe a Goodyear-welted brogue wingtip in brown and black belongs in every well-dressed man’s wardrobe, there are other options that would also be worth owning, that may also be a bit more comfortable.

3 Tips On How To Dress Well And Stay Comfortable
Click image to enlarge in new window || Meermin, $340 (Goodyear), Beckett Simonon, $199 (Blake)

In particular, take a look at a shoe with a Blake construction. The overall benefit to Blake-constructed shoes are: thinner soles, a generally lighter weight, and more flexibility, making it easier to wear.

This, of course, is in comparison to a shoe made with a Goodyear welt construction. (A more detailed explanation here.)

One of the main benefits to a Goodyear-welted shoe is the fact that they’re finished by hand and can be resoled down the road. With Blake construction, most need to be resoled with a specific machine, which can be costly and not as easy.

Each type of shoe has its strengths and drawbacks, but now, you know the major differences and can choose wisely.

4. (Bonus) Do your clothes actually fit?

This should’ve probably been #1. The best way to be 100% comfortable is to make sure your clothes fit your body well.

Formal garments (shirt might be.

These garments are meant to drape and have clean lines, i.e. as little pulling, wrinkling, and stacking as possible.

In the photos below, the two on the left are examples of good fit and drape, the two on the right are waaay too tight.

3 Tips On How To Dress Well And Stay Comfortable
Click to enlarge in new window || Good drape examples, left: @andreasweinas, @dressduckwho

So, as far as fit is concerned, your suit jackets and trousers should fit more like photos 1 and 2, and (a lot) less like photos 3 and 4.

You don’t have to sacrifice sharp looks for comfort

Most guys who only dress casually think dressing up means being restricted, hot, and uncomfortable. Effortless gents know that’s not the case at all. You can dress well and be comfortable; those two things aren’t mutually exclusive.

It all boils down to nailing the perfect fit for your clothes and body type, and from there, choosing the right details to make sure you’re not feeling restricted, overheated, or uncomfortable when on your feet.

By the way, don’t forget to grab yourself a Mizzen + Main shirt. Right now you can snag 3 dress shirts and get $50 off, just use code MAINMAN3 at checkout.

How do YOU stay comfortable while dressing sharp? I’d love to hear what you do in the comments below.