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A Menswear Stylist Shares Her Must-Have Holiday Shopping Picks

From gifts for your grandpa to your partner, here’s what she recommends.

How To Shop Like
A Menswear Stylist Shares Her Must-Have Holiday Shopping Picks

Welcome to our How to Shop Like series, where we spotlight personalities within the fashion industry and take a deeper look at how they shop—think all the best insider tips and tricks. This week, we're chatting with celebrity stylist and founder of LEOIlaria Urbinati about shopping for gifts for all the men in your life.

Celebrity stylist and founder of men’s lifestyle website LEO Ilaria Urbinati spends her working hours thinking about the way that men curate their lives, whether that’s via fashion, interiors, food, or film. Needless to say, we were hard pressed to find someone better to tap for advice when it comes to gifting the guys in our lives. From co-workers to family members to partners, she’s not only recommending specific items she keeps in her arsenal but walking us through her approach, as well. From start to finish, here’s how Urbinati approaches her holiday shopping—her tips could apply to anyone in your life.

Shop Ilaria’s Gifting Picks:

Cryo II


Chelsea Boots


Grill System

Fire & Flavor

Utility Apron


Lambswool Cable Crew

Todd Snyder

How do you start when you’re gifting a man, whether it’s your partner, relative, coworker, or friend? What kind of things should you consider?

“Any hobbies or things he collects are always a good start. For example, say he’s into collecting kitchen knives, you could do a little research into some cool, rare Japanese knife sets. If he’s into photography or film, you could get him an awesome art print from a company like I got my husband a framed black and white of Michael Caine last year. If he’s into something like fishing or camping, maybe some new gear. Just really think about what he’s into and then ask yourself what he’s missing in that regard. If they’re into grooming, a new Dopp kit is always great and most guys need a new one every few years.

“As far as clothing goes, I find that boots are always a no-brainer or a great sweater. You don’t want to get into gifting things like pants because it's complicated and things like ties are a little cliche.

“If its a dad or grandpa, I like to order a print of a great shot of the family or kids or grandkids and have it custom framed (or a regular frame will do, too) or order one of those custom photo books—I got my dad a whole custom book of the grandkids last year. It was like a year of their life in one book printed and made into a beautiful fabric hardcover book. He will have that forever.”

Do you prefer experiences or material items?

“For a birthday, I prefer experiences, but for Christmas, I do like something I can wrap and place under the tree. That said, I love the idea of surprising someone with tickets to see one of his favorite sports teams, a favorite band, or a weekend getaway. You can always print out the tickets and place them in a nice box to gift wrap.”

Do you consider trends or “of-the-moment” items, or do you focus more on the personal preferences of the giftee?

“Always go personal. Men are not so trend driven.”

What are your thoughts on gifting for men within your professional sphere?

“For gifts for clients or co-workers, I usually figure out one cool thing that is an obvious pleaser and could work for anyone, then gift everyone the same. If I start gifting every one of my clients an individual, separate gift, my brain will explode. That said, it can still feel cool. Something like a cool gift set of socks from a fancy sock company like London Sock Co or a booze box set from Flask & Field will make anyone super happy.”

Is it okay to subtly push a man outside their comfort zone with a gift (specifically in the realm of style)?

“A gift is not the ideal time to push someone out of their comfort zone. If I buy Johnny (my fiancé) something I love (but that I’m not sure he’ll be down with wearing and am trying to convince him), that’s something I’ll get him not as a holiday gift. Save those for a just-because gift some other time and see if he’s into it. That way, if he doesn’t like it, I can just return it and there’s no disappointment. When gifting someone for Christmas, you want to know that when they unwrap that box, they’re going to be really excited. This is not really the time to get experimental because then it can sort of become about you and not about what they want to receive.”

Is there anything you gravitate towards when you’re on a budget or don’t think it’s appropriate to spend a large amount of money?

“A coffee table book is a no-brainer—they range in price and are appropriate for everyone, including a co-worker. A great coffee table book always makes an impression, and it can still feel personal. For example, if he’s into boxing, a gorgeous Muhammad Ali book shows you’re paying attention. There’s pretty much a coffee table book for any interest, and they always look great in anyone’s home. If I want to make an impression on a budget, a leather bound writing journal from a fancy brand like Montblanc is only $70 but looks impressive. If I’m really on a budget and looking for a stocking stuffer, an actual reading book is great too ( if they like to read) and are usually around $20.”

Are there any fashion items you suggest if you don’t know someone’s exact size? Should you guess a size or should you steer clear of that realm?

“A sweater is the safest and easiest style item to guess as it usually goes by S, M, L, XL, etc. and has stretch. Also, what guy doesn’t love a sweater? It’s the absolute no-brainer gift as far as clothing goes.”

Are there any catch-all gifts that are a safe bet for most men? Anything you should avoid here?

“Something that works for everyone and is always a safe option is a nice bottle of their favorite booze. For clothing, I would do a knit polo or sweater.”

Any foolproof umbrella categories (i.e. gadgets, cookware) you often gravitate towards?

“Men just like gear and gadgets in general. They are sort of collectors by nature. If they’re into cooking, you can never go wrong with Le Creuset. Try a new pot or pan. Plus, they even have a great coffee maker that just looks beautiful on the counter.”

What are you planning to gift your partner this year?

“If I tell you, I have to kill you! But there’s always some clothing in the mix, and then something to do with one of his many hobbies.”

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