Gift Guide: For Guys, But Make It Fashion

Everyone knows that men can be painfully difficult to shop for during the holidays—especially when it comes to buying them clothing. So we turned to our partners for some fashionable gift ideas… which, let’s be honest, meant we just turned back to ourselves because the both of us have years of experience dressing our guys. Here’s just a few suggestions that have been crowd favorite gifts in the past, or made the wishlist this year!

1. Clark’s Desert Boot (7-15) / 2. Denim Jacket (XS-XXXL) / 3. Shawl Collar Sweater (S-XXL) / 4. Fun Print Shirt (S-XXXL) / 5. Pom Pom Beanie (OS) / 6. Joggers – Straight Size (S-2XL), Big & Tall (MT-5XBT) / 7. Plaid Button Down (XS-XXXL) / 8. Traveler Jeans (28W-44W)

1. Clark’s Desert Boot / $56

Summer / These Bushacre desert boots are a ubiquitous staple in fashionable men’s wardrobes—a cursory glance of r/malefashionadvice will have you awash in a sea of “CDB” (Clarks Desert Boot) references. I can see why, I can’t speak to the comfort, but they are affordable and super versatile. They work for the office, casual attire, date night, almost any occasion. My boyfriend is on his second pair after having completely worn out the first—both in the beeswax color if you’re curious. If you have a “I only need to own two pairs of shoes” type of man in your life, do him (and yourself) a favor and grab him some CDBs.

2. Denim Jacket / $40

Summer / After years of wearing the same North Face (that matched nothing in his closet), I finally got my boyfriend to commit to a jacket that isn’t black, fleece, or logo-laden. He settled on this denim jacket, which I liked because the light wash will tone down the Canadian tuxedo vibes with his dark wash jeans. The sherpa is cozy enough to keep him warm for most days of Mississippi winter, and it can dress up some joggers for an athleisure moment. It won’t work for a formal office, but it is a small step toward getting your man out of his zip-up hoodie rut.

3. Shawl Collar Sweater / $35

Kathryn / My mom got my husband a heather grey shawl collar sweater for Christmas last year, and at first he hated it. And then he wore it once, then twice. Then three times. Now it’s one of his favorite winter wardrobe staples. He can wear it to work if it’s especially cold out, or out to date night. This similar one from Kohl’s has the same silhouette and the speckle pattern matches my new Old Navy sweater (similar)—there may be a matching couple’s outfit in my future.

4. Fun Print Shirt / $27

Kathryn / There was a time when my husband only wore graphic tees. One summer I gave him a boat-patterned short sleeve button down shirt, which he proceeded to wear every day until about Christmas 2017. For that holiday, Summer gave him a lobster-patterned shirt that he wore just about every day, and when he didn’t, he wore the boat shirt. It was then that I realized we cracked his signature style: bold patterned short sleeve button downs from Old Navy. It’s his closet staple. Maybe these are a new closet staple for a guy in your life. Or maybe they just need something fun to put into their rotation. Old Navy has SO MANY fun patterns, including some awesome dinosaurs this year!

5. Pom Pom Beanie / $17

Kathryn / It’s pretty much a sin in the south to go outside when it’s cold with a bare head. My husband, who is from the northeast and hardened to any cold Texas could throw at him, is not much of a “hat” guy, but maybe a hat in his school colors could win him over. If your man isn’t a fan of red and blue, this hat comes in another color and has fleece lining which makes it super soft and cozy.

6. Joggers / $15 (Straight Size) or $23 (Big & Tall)

Summer / The other day on the phone Kathryn’s husband said “I’m gonna wear joggers out, I think they look cool,” and y’all, he’s not wrong. Joggers can look cool if you style them right; like I said, I’m a fan of the denim jacket+jogger combo. I usually find a decent pair at Marshall’s, but this pair from Target is on sale so they’re a better deal than I usually find. Plus, they come in a bunch of colors and Big & Tall sizes, because you know we’re all about size inclusivity over here.

7. Plaid Button Down / $35

Kathryn / A plaid button down can be perfect for the holidays or to wear to the office. A shirt like this was another one of those gifts from my mom to my husband last year that didn’t initially go over well, but now he wears them all the time. Old Navy has so many different patterns, and this style is great because it is thin cottony material, not flannel, so it can carry over between seasons.

8. Traveler Jeans / $129

Summer / Speaking of those dark wash jeans, these are the only ones he wears. They’re a little pricy and he owns two pairs, but he wears (and raves about) them constantly. If you’re going to invest in a clothing item, a pair of jeans you wear three times a week isn’t a bad choice. These are great because the wash works for a casual office and makes your weekend-wear look a little more dressed up. If you prefer a khaki look, they also come in four colors of chino. The fabric is stretchy so they’re super comfy, they’ve seen many a road trip and plane ride without complaint.

Honorable Mention: Duluth Trading Co Buck Naked / $21+

Kathryn / We talked about clothes for your guy, but what about what’s under them? My husband is obsessed with Duluth Trading Co’s Buck Naked underwear. He got me some women’s underwear as well, and I am such a fan. They come in both standard solids and fun patterns!

FTC: This post contains affiliate links. Whenever you purchase something from one of these links, we at Tailor of 2 Cities earn a small commission at no additional cost to you. We only post items that we love or want ourselves. When you purchase from these links, you’re helping to keep our little blog going and we appreciate your support!

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