Looking Good and Feeling Good: Things Guys Never Consider When Buying Clothes

Stylish man

Oftentimes, dressing up is synonymous with being uncomfortable. You button your shirt all the way, tuck it in, add a tie, throw on a suit (or at least a suit jacket), put on your dress shoes and you’ve set yourself up for a pretty miserable day. Luckily, it doesn’t have to be that way. You can actually look good and feel good at the same time. Tired feet and sauna boxers will be a thing of the past if you know what to buy.

The Dress Shirt

Thread count is key for dress shirts.

Fabric quality is essential when it comes to a comfortable dress shirt, and just like with bed sheets, a higher thread count means softer fabric. Aim for a shirt that has a thread count between 100 and 120 and opt for two-ply fabric, especially if you live in a mild climate. If you go any higher you risk ending up with a very warm shirt that will trap in your body heat.

If you’re shopping for a summer shirt, go up to a thread count of 150 and opt for single-ply fabric for a high-quality shirt that will look and feel great. The cost goes up when you increase the thread count, but so does quality. I’d rather buy five $150-$200 shirts in a year than 10 $50 shirts. Thomas Mason Ludlow shirts from J.Crew are great shirts in the $150 range.

The other thing you need to consider is which type of fabric you like. This comprehensive guide will help you decide what’s best for you — ultimately, this choice comes down to personal preference.

The Undershirt

White Jockey t-shirt

Breathable materials are commonplace when it comes to athletic gear, but you might not have noticed that several companies are applying that same technology to everyday undershirts. Let’s face it, spending money on a nice dress shirt isn’t going to do you any good if your old cotton T-shirts are acting as heat furnaces.

Jockey has a staycool collection of T-shirts that regulate skin temperature, keeping you from feeling sticky all day. You can get a 2-pack for around $27. They might cost a little more than what you’re used to, but you’ll notice a big difference.

The Pants

Cotton chinos

Before we get into comfort and pants, let’s make a promise to never wear pleated pants ever again. It’s almost as bad as wearing white tube socks and sandals. Don’t do it.

Getting back to comfort, it’s mainly about fit and whether you prefer jeans, chinos or dress pants. Slim fit (my personal preference) is way different from skinny. I know skinny jeans on guys have been semi popular for a while now, but there’s no way you can convince me they’re comfortable.

If you buy boot cut jeans I hope you also wear boots a lot, otherwise what’s the point? When it comes to comfort and style I really enjoy a good pair of slim-fit cotton chinos. H.E. by Mango has great ones for around $60 or less.

The Underwear

ExOfficio boxer briefs

Workout boxer briefs are so comfortable you want to wear them every day. At least I do. The downside is that they can be very tight, which is OK if you only wear them during your workout. If you wear a pair all day, however, you want some more breathing room, regardless of how great the moisture wicking is.

This is why I love ExOfficio. They have the most comfortable underwear I’ve ever worn. I even consider hand washing them between laundry days just so I can wear them more often. The Give-N-Go Sport Mesh boxer briefs (one of several models) are tight, but not too tight. The material is stretchy, soft and you barely feel that you’re wearing them — even on hot days. They’re roomy in the front, providing more breathing room, but still keep everything in place.

The downside is that these types of underwear cost quite a bit (around $30), but there’s no going back after trying them. My suggestion: Buy a new pair and throw out old ones every month until every day is Good Underwear Day.

The Socks

No-show socks

Nothing detracts more from a great shoe than ugly socks, and if you’re wearing shorts, there’s no way you can hide them. To solve this problem, opt for no-show socks. They’re designed to stay on your feet without showing when wearing shoes. It’s a great way to avoid those unfortunate tan lines that make it look like you’re wearing ankle socks when you’re actually barefoot.

There are lots of options out there, but I like these ones from Sperry Top-Sider because they have a small grip pad at the heel that keeps them from slipping down. There’s less fabric on your foot, so they won’t get as warm as traditional socks. Give them a try at $18 for a three-pack. If you’re new to the no-sock look, ease into it with this guide.

The Shoe Insoles

DoctorInsole shoe insole

I love wearing dress shoes, but my feet always cramp up because the soles are usually hard and flat. It doesn’t help that I’m flat-footed on top of that. Getting custom-made insoles from a doctor can cost several hundred dollars, and more affordable options usually don’t last very long or they don’t provide enough support.

The insoles from DoctorInsole™ seem to be a middle ground between the two. A pair of insoles cost $50 and wearing them is a surprisingly pleasant experience. They’re sturdy, comfortable and come in different models depending on what type of shoe you wear (dress shoes or athletic shoes).

I recently spent five hours chasing after a 5-year-old at the San Diego Zoo and experienced no cramping or fatigue in my feet. I can’t think of a better way to battle test these things out, so they’ve earned their place as a wardrobe staple. If you’re on your feet a lot, do yourself a favor and try these out.

These are some of the products I’ve discovered that has made dressing for any occasion a lot more comfortable, but I’m sure there’s more I have yet to discover. What are some of your favorite wardrobe choices when it comes to mixing style and comfort?

Photo credits: Getty Images, Luke Wooden, Jockey, H.E. by Mango, ExOfficio, Sperry Top-Sider, DoctorInsole

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