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Tis the season to be bombarded by gift guides. But instead of doing a highly generalized, throw-everything-against-the-digital-wall mega post, we’ll be breaking it up by category and dropping multiple guides in the coming days. Gifts for that somebody who likes watches. Or the guy who’s really into shoes. Or the Dad who makes time for style. We’ll cover all those, and hopefully a few more over the next week or so. 

A (slightly unexpected) Pocket Square – $14 and up (way up)

• Kent Wang Made in France Star Chart Burritt Pocket Square – $45 – $65 shown above
• Todd Snyder Made in Italy Wool Foulard Pocket Square in Rust – $45
• The Tie Bar Holiday Snow Day Printed Silk Pocket Square – $24
• The Tie Bar Domino Dots and Paisley Navy Pocket Square – $14
• Spier and Mackay Blue and Gold Paisley Silk Pocket Square – $28

A crisp white pocket square is always gonna look good. But since he’s probably set on those basics, go for something different. Try something saturated, or in a wool fabric, or maybe a micro print.

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Storing suits sans garment bags is asking for moth-trouble. Storing them in suffocating, cheap plastic bags is asking for rank saturation. Bags like these are the answer. Breathable but still dust and water resistant, with a plastic window that allows you to see just which suit you’re grabbing off the rack. Perfect.

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Change their socks, change their life. If you had to pick one type/model of socks that you’d be forced to wear with everything for the rest of your life… from working out to wearing with a suit and tie… these are the socks. No really. They’re that comfortable. That versatile. “The Standard” from Darn Tough are those socks. Perfect for wearing with suits, sportcoats, jeans, t-shirts… they do it all. Made in the USA, extra cushioning protects without being overly bulky (can’t say that about a lot of dress socks), and made from temperature regulating and moisture wicking merino wool. Machine wash gentle and tumble dry low.

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Is it the sexiest gift? No. But wide shouldered hangers are gold, GOLD Jerry!… to a guy who loves to wear suits, sportcoats, and blazers.

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If the person you’re looking to give a gift to wears suits often, then they’re almost certainly in dress shoes often. And that means using a shoe horn. Made in Denmark from real horn sourced from Nigeria. And sheesh, for such a utilitarian piece, it sure looks great.

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Sticky rollers are great for quick jobs or more casual clothes, but if he really likes his suits and sportcoats he might think twice before taking an adhesive roller to it. That’s where a clothes brush comes in. They’re specifically designed to lift dirt and hair out and up from a suit’s fabric without damaging the weave. Kent makes really nice clothes brushes. Shown above is an older model of the two sided (soft/stiff) bristle brush. Spendy? Yes. But he’ll have it for the rest of his life.

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Skip giving him cheap ties. If the guy on your list wears suits a lot… he knows where to get cheap ties. Instead (if he’s been extra nice this year) opt for a splurge-level-tie. Like this classic, silk grenadine tie from Kent Wang. Solid in color but with that unmistakable texture. Made in Italy. And unlike cheap ties, the construction and quality/weight of fabric makes it tie easier and drape better.

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• Bespoke Post Halfday Garment Duffle – $95
• Hook & Albert Garment Weekender Pro – $337.63 ($675) (shown above) 
• Briggs & Riley 22″ Garment Duffle Bag – $369

These are the duffel bags that are designed to unzip and unroll into a traditional garment bag. Perfect for transporting suits and sportcoats (and the accompanying shirts and shoes and what not) while reducing wrinkle risk. Available at many brands and at MANY price points, you can find a review of the (cheap!) Bespoke Post option over here.

A Gift Certificate to their Tailor

There’s always something that can be tweaked just a bit better. A jacket to let out. A new coat to bring in a little. Shirt sleeves to adjust. And a lot of us are coming out of the pandemic with clothes that need to be let out or taken in.

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Why a gift card instead of just outright buying the shirt? Because of all the customization options the recipient will get to chose. An enormous amount of fabric choices, three fits, sleeve lengths in half inch increments, and six different collar styles. The non iron fabrics are of particular note, with their silky finish. They’re just excellent. Production takes 4-5 weeks after ordering since they’re made-to-order. Shown above is the Sanders Non-Iron Fine Twill, which was recently reviewed over here.

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As necessary as the dry-cleaner can be if you’ve seriously sweated up or otherwise soiled your suit… dry cleaning is absolutely terrible on suit fabrics and construction. The way to keep your good suits lasting longer is to use a steamer to freshen them up/get wrinkles out. Dry clean as little as possible, and use something like this instead to make your well-loved (and worn) suits feel and look as good as new. A large water reservoir, anti-calc function, easy to hang clothing-station, and wheels/collapsible pole for easy storage, all make for one heck of a “no it doesn’t need to go to the dry cleaner yet” tool.

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Expensive for sure, but wearing a polo with a suit or sportcoat is kinda like wearing a turtleneck with a suit or sportcoat. Only you are totally not wearing a turtleneck with your suit or sportcoat. The turtleneck thing is an advanced style move that requires a lot of confidence of which not all of us possess. Polos are so much easier, and Tenet showed they look terrific worn this way. The Rhone Commuter is a long sleeve polo with a hidden button down collar (a must if you’re wearing a polo with a suit or sportcoat) that’s made from the same fabric they make their excellent breathable, high-stretch, wicking button down shirts from. Translation: They’re performance wear that doesn’t look like performance wear. So you’ll be super comfortable no matter what. Expensive, yes, but worth the (major) splurge for some. Popular enough that they sell out almost immediately when they restock. So signing up for a notification when they restock might be worthwhile.

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For when he gets home and wants to relax. Made in the USA from Horween Chromexcel leather or suede. Genuine Handsewn Moccasin Construction. Italian Wool Linings. The opposite of cheap, gross feeling, department store slippers. Currently 25% off, but sizes are selling really fast.

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• Chalk Stripe Track Jacket in Cotton/Wool – $157.20 w/ EXTRA20 ($378)
• Houndstooth Track Jacket in Cotton/Wool – $139.20 w/ EXTRA20 ($348)

Ridiculous as a concept (a $380 originally priced track jacket?!) but those can be some of the most fun gifts. Because not many are gonna buy something like this for themselves. Athleisure, but made from cotton/wool blend fabrics that look like they were lifted from Savile Row. Made in Portugal. Final sale though. No returns or exchanges. So they’re a massive risk.

A Suit Valet (prices varies)

The Pick: Proman Products Excalibur Wardrobe Wood Valet Stand – $149.99 ($199)

One way to dress a little better in our increasingly casual world is to set out what you’re going to wear the night before. A valet stand is perfect for those who prefer to dress up (even if they don’t have to). It’s also a really good wind-down evening tradition for a lot of us. Helps us turn off screens, disconnect, and get ready to truly rest and recharge. These things are increasingly hard to find but sure are handy. Amazon has some, but just make sure you get it fulfilled by them in case it shows up damaged, busted up, etc. That way you can easily send it back (don’t trash the box before inspecting/assembling). If you can find a cool vintage one, that might be the real bee’s knees.

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Even if he never goes double breasted with his tailored wear, those have to be the perfect sweaters for those who love to wear suits.

A simple (but interesting) dress watch

• Baltic HMS 002 Automatic Watch – $390ish
• Dan Henry 1937 Dress Chronograph – $270  (reviewed here)
• Orient Bambino Small Seconds Automatic – $203  (reviewed here)
• Lorier Zephyr Automatic – $499

A watch given as a gift can hold high significance. How can you not think of the person when you wear it and glance down to look at the time? Your giftee almost certainly already has a go-to, simple dress watch. So something slightly different could be a fun way to mix it up. Think: a simple dressy chronograph, or a watch with a different case shape.

A Dressed Up Dinner Out

A nice dinner out isn’t just about the food. It’s the good lighting, the good furniture, and the talent on display by those making the drinks and food for us. And it’s a great reason to dress up.

Want more gift guides? Head here for the soon to be growing archive of our 2023 gift guides.