Weekend Edition #35: How To Dress a Guy in Ten Ways

A Style (and Gift!) Guide for the Guys

Hi!

I hope you had a happy Thanksgiving, a delicious meal, and a fun outfit! What did you wear? Tell us in the comments! As planned, I went with cheetah to gobble down lots of turkey.

Jacket on sale here, leopard jeans almost sold out here (the Gap!), boots on sale here!

I mentioned in last week’s post that I wasn’t going to send a newsletter this week…

(Sidenote: did everyone get last week’s post? It went straight to my husband’s promotions folder, so if you missed it too, check there or click here. It’s all about my recent work trip to Amsterdam, think less gouda and more good outfits!)

BUT, I was shopping in stores on Monday and Tuesday this week for work (aka checking out the competition) and got inspired!

I was specifically looking at men’s brands for work, and I don’t know about you, but I am married to a guy who is very hard to shop for. Much less dress. And I’m in the biz, as they say!

So, in the spirit of the world’s best rom-com (or at least a strong contender), I’m going to share my ideas on How to Dress a Guy in Ten Ways. Hope it’s helpful!

moodboard

LOOK BOOK

I imagined five “guys” and offered a traditional and modern take for each one, to get to ten brands for you to explore during Peak Sales Period. Happy shopping!

For the Preppy Guy

It’s all about cozy sweaters and relaxed-fit pants. It’s time to move from a cotton crewneck sweater to a brushed wool one, and it’s really time to try a sweater polo. Just like skinny jeans have been dethroned for women (but it’s ok, you can still wear them, just mix in some other fits, too!), men’s pants are loosening up. Upgrade the slim chino he’s probably been wearing for the last 5 years (or longer!) to a straight, or even better, a relaxed straight. Then, try a wide wale corduroy in a wider fit, for something old that’s new again.

1. J.Crew (Traditional)

I love this Johnny-collar mesh-stitch sweater polo that was inspired by styles from the 1950s paired with the Broken-in Straight chino, J.Crew’s newest chino fit inspired by the classic chinos of the 90s, but cleaned up for today. The rugby stripe color combo in this Brushed Wool Sweater Polo is so good (it’s almost sold out!) and these 10-wale corduroys in a classic fit are cooler than the cords from our prep school days. Want to step it up a notch? Go for these cords in a pleated trouser fit with an embroidered skier critter. Wear with this brushed wool crewneck for the perfect cookie exchange party look!

2. Todd Snyder (Modern)

Todd Snyder used to be the Head of Men’s Design at J.Crew, so this is an excellent brand to upgrade your J.Crew guy to if he’s ready for something a little more modern and luxurious. Todd Snyder elevates classic styles with super soft fabrics and updated fits for a fresh take on preppy style. I love the 100% cotton relaxed chino with this gorgeous button mock sweater made from organic cotton, wool, and alpaca (perfect if you have a ski trip planned). For the holidays, this cable sweater in the perfect shade of red with a casual 5-pocket pant in a super soft Italian fabric made with cotton and camel hair. Like a sweatpant in hard pant form. And finally, since the J.Crew rugby sweater is almost sold out, snag this one to wear with this wide wale cord pant that has elastic at the waist - an ideal outfit for both outdoor winter activities and lounging at home by the fire.

For the Casual Guy

I almost called this guy “Dad Guy,” but while this guy may love to mow the lawn, and grill, and pop open a cold Coors (or Athletic Brewing Co.), he’s also so much more than that. Maybe he lives in Brooklyn, or the Brooklyn of New Jersey (Montclair), maybe he’s a Girl Dad, or maybe he’s the best chef in the house. Or the artist. Either way, this guy is casual, comfortable, and cool. Dress him in a shirt jacket, a barn coat, and a tote, and send him on his way to dominate the day.

3. L.L. Bean (Traditional)

This is the field coat that launched all the other field coats. Originally designed in 1924, it’s a classic for a reason. Wear it over the Signature 1933 Chamois Shirt, another OG, in either a solid, heather, or plaid flannel made from 100% Portuguese cotton. The L.L. Bean Boat Tote is an icon for a reason, but I’m actually partial to the Nor’Easter, which I own and love for travel. It just fits under an airplane seat (if you give it a good shove), and it holds everything. It’s perfect.

4. Alex Mill (Modern)

Somsack Sikhounmuong is the creative director and co-founder of Alex Mill, which was founded by Alex Drexler, son of Mickey Drexler, the menswear legend and former CEO of Gap and J.Crew. (Retail is a very spidery web of connections.) His taste is pitch-perfect, and he writes a wonderful substack . I love how he is combining preppy, sartorial, and outdoorsy influences at Alex Mill to create a multifaceted wardrobe for the modern, casual guy. The Frontier Jacket is inspired by a 1950s barn coat, with added details like a corduroy collar and half-flannel lining and a relaxed, modern fit. Wear it over either their take on the chamois shirt, the Highland, which is cut from super soft flannel and has western-inspired pockets on the chest. For a slightly more modern interpretation, try the Ethan flannel shirt, which has an open collar and hem. I love the black plaid, and I also love the Perfect Weekend Tote in black, too, for a contemporary take on a classic.

For the Classic Guy

I love a guy in a suit. However, I can count on one hand, maybe one finger, how many times a year my husband wears a suit. And I bet it’s the same for you. My answer to that? A sport coat (a.k.a a blazer) and a favorite pair of pants. Could be denim. Could be a 5-pocket twill pant. Could be a chino, a corduroy. Slim leg. Straight leg. Relaxed leg. The options are endless. It’s the suit for the guy who doesn’t need or want to wear a suit. And he’s going to look good. (P.S. Did you know that a button-down shirt refers to the buttons at the collar, which originated in the late 19th century with British polo players who added buttons to their collars to keep them from flapping in the wind while they played? A button-up shirt does not have buttons at the collar, and is considered the dressier option.)

5. Brooks Brothers (Traditional)

   

   Brooks Brothers is the oldest American clothing brand, and they’ve built their business on excellent tailoring. They introduced both the ready-to-wear suit to American customers in the 19th century and the button-down shirt (c/o those British polo players) in the early 20th. They still have tailors working in their stores to give you the perfect fit, and they just opened a brand new flagship on Newbury Street in Boston. The grey Plaid Tweed Sport Coat is cut from tweed woven by the UK's renowned Abraham Moon & Sons mill, and I love it with this rich inky navy button-down made from Portuguese flannel, long considered the purveyors of the softest flannel in the world. The Glen Plaid Sport Coat looks so fresh with a Chambray Shirt (wear with dark denim), and the Camel Hair Sport Coat features fabric woven by Italy's renowned Loro Piana® mill. I’ve felt this person, and it feels so nice. Love it with this Brushed Twill from Italy’s Albini mill. Wear this with a navy 5-pocket pant or chino to a holiday party, or if you need a super refined look, this grey Italian merino wool dress pant.

   6. Sid Mashburn (Modern)

   

   Sid Mashburn was J.Crew’s first men’s designer (see, the tangled web!), and he later designed for Ralph Lauren, Tommy Hilfiger, and Land’s End. He grew up in the South, and while his roots are classic and heritage, his aesthetic is fresh and modern. The corduroy Butcher Jacket is halfway between a chore coat and blazer, so it can be dressed up or down. (Sid offer’s a matching pant if you want to go for the full bonanza!) I love it with the ultra-classic striped Oxford Shirt from Portugal. For something in the color of the season (that would be chocolate brown), check out this fully canvassed Glen Plaid Tweed Jacket with a handmade chambray shirt. Lastly, for the guy who has everything, splurge on this gorgeous 100% cashmere Ghost Blazer, which is super light-weight and will be the most beautiful, and useful, piece in his closet. I like it with this classic Tattersall Poplin shirt.

For the Sports Guy

My two favorite winter sports are skiing and running. The former requires all the gear and the latter requires almost none. But as I’ve learned from living (and running and skiing) in cold weather places like Wyoming and Amsterdam, the Scandi adage that there is no such thing as bad weather, just bad clothes is mostly true. So here are some good clothes to get your guy playing through any weather.

7. Patagonia (Traditional)

   

   As a new student at prep school, Patagonia was one of my first brand obsessions after Birkenstock. I wanted a Patagonia fleece so badly, to go with my Boston clogs. The brand is still so reliable, and I love what the company stands for. These heavy duty shells (jacket and pant) look great. Their Nano Puff is a longtime bestseller, and every guy (and girl) should have a pair of base layers.

8. Stio (Modern)

   

   Stio is a small Jackson Hole-based brand, and the product is designed by the people who wear and use it day-in and day-out. It’s great. My husband and I have been skiing in versions of this jacket and pants for years. (I still have the OG one from launch.) This lightweight down jacket is great on its own for cold-weather running/walking or under the jacket for epic ski days. The Glide Power Stretch Half Zip and Joggers look perfect for running, skiing, traveling, and hanging out at home. What more could he want?

For the Sports Fan

Some people wear the heart on their sleeve, and some guys wear their favorite sports team on their chests. If you’ve got one of those, I’ve got some cool, good-looking, and dare I say, fashionable, fan gear for you.

9. Ralph Lauren (Traditional)

This works best if your guy is a Yankees fan lol. But I love this Ralph Lauren x MLB collab. These are some of my favorite picks, but there are some super luxe items in the collection for the guy who has everything but doesn’t have a Purple Label RL x Yankees Cashmere Cardigan ;)

10. New York or Nowhere (Modern)

    

    Ok, this one is kind of niche, but I’m banking on having a lot of NYC readers here! This is a hyper local brand that does awesome collabs. Check out their Knicks one here, Yankees here (lots sold out but some super cute kids stuff left!!), Rangers here (lookbook only, available at Madison Square Garden), and the NYC Marathon here.

    We did it! How to dress your guy in ten ways. Happy shopping!

EXTRA THOUGHTS

• Aaron Levine was the former head of design at some of the most influential men’s brands in the biz, and he just launched his own brand. He’s doing the media rounds and is super smart and passionate about all things menswear and clothing. Check out How to Get Dressed with Aaron Levine c/o

  Leandra Medine Cohen
  or listen to Lauren Sherman’s Fashion People podcast with him.

• John Jannuzzi
  is another menswear expert and great writer who just published How to Dress Well Without Regretting It and it’s chock full of goodness

• I’ve followed

  Michael Williams
  for years - his taste and aesthetic is second to none. Check out his gift guide for truly excellent recommendations.

• Jennifer Cook
  wrote a super fun non-gift guide gift guide,
  Sarah Shapiro
  gave us another excellent round-up of all retail and fashion news

WHAT I BOUGHT

• Too much. I bought too much. I read everyone’s excellent advice like

  Elizabeth Cardinal Tamkin
  who recommends to replenish your “Back Pocket Wardrobe,” and
  Sarah | Fewer & Better
  who only shops for things on her list, but I unwisely ignored all of it and followed my itchy finger and gut. I avoid final sale like the plague, and anything that doesn’t feel as right on as it did on my screen, I return. I’ll do a round-up of what I kept next week.

THANK YOU for being here. I love writing this newsletter every week and connecting with you all. I’m so grateful. Have a wonderful weekend!

x Lindsay