Today’s issue suggests some items that will be restocked when winter comes again. If you want to bookmark any of those or anything else you’re thinking about buying, I recommend the app Carted, which alerts you when items are restocked and go on sale.
Today’s guest piece is by Derek Guy, whose commentary on menswear I’ve been addicted to for years. Over the last eight months or so, men I know have been asking me about what jeans they’re supposed to buy now that skinnies are over. To which I usually say: I’m not a stylist! But here’s something from Nordstrom that worked for my husband! I knew that Derek would be the perfect person to ask to create a comprehensive guide to moving on from skinny clothes. Ahead, his suggestions for how to loosen up everyday menswear, whether you wear it or find yourself tasked with picking it out for someone else.
—Amy
Skinny Fits Are Over. Here's How to Loosen Up.
By Derek Guy
A few months ago, a friend who runs a small business told me his younger Gen Z employees staged an intervention — like that Christopher Moltisanti scene in The Sopranos — to inform him that he needed to stop wearing slim-fit pants. Much like how Millennials rejected baggy trousers because they associated the look with Boomers, Zoomers are now distancing themselves from their Milennial coworkers’ slim cuts.
Over the last 25 years, slim fits have gone from cutting-edge to passé. The trend took off in the early 2000s when Hedi Slimane and Thom Browne shrank menswear as a reaction to oversized ’90s silhouettes. The Strokes made skin-tight jeans and tourniquet tops aspirational, and fashion writers framed slim tailoring as settled science. Decades later, everyone from President Barack Obama to Elon Musk wears trim clothes.
The shift toward looser silhouettes began in early 2016 when Raf Simons sent models down the runway in oversized bubble parkas, topcoats, and moth-eaten tennis sweaters with hand-engulfing sleeves. I think the death knell happened in 2022 when J. Crew reintroduced their Giant-fit chinos. Or maybe it was when that photo of a little French bulldog went viral on social media.
Rather than letting designers, fashion writers, or Gen Z employees dictate your wardrobe, it’s better to think of dress as a social language shaped by cultural history. Skinny black jeans will always work with black leather jackets and black boots because of the legacy of seventies and eighties punk. Similarly, trim suits with cigarette trousers can still evoke sixties Mod cool. However, the ubiquity of slim-fit clothes and clear indicators from the fashion industry that trends are changing have left many men wondering how to loosen up. Here are some ideas.
Workwear Pants
If you’re “loose-fit curious” but haunted by memories of nineties business casual, start with workwear. Utilitarian styles — double-knee carpenter pants, OG-107 military fatigues, army chinos — look great in a roomier cut because they were originally designed for movement. Carhartt and Dickies offer solid double-knee options, while Ralph Lauren, Imogene + Willie, Standard & Strange, and Kapital carry canvas and denim versions that break in beautifully. For military fatigues, try Stan Ray, Orslow, or the vintage originals (call up Wooden Sleepers). Bryceland’s also offers a more wearable take on military-issued P-44s, charmingly known as “monkey pants” to inveterate thrifters. Theirs features the spacious side pockets that were originally designed to hold military food ration packs, but they don’t have the gas-mask-holding butt pocket that will confuse your coworkers. Just note that these have a very high rise, so they work best with untucked shirts and outerwear.
These pants pair well with plaid flannels, denim Western shirts, or chamois button-ups with the soft, napped texture of a well-loved billiards table. Layer on some utilitarian outerwear — a chore coat, denim trucker jacket (new here), black double rider, or fishing jacket. The Parisian second-hand shop Brut has an in-house line of brand new vintage-inspired clothes. Their outerwear is great for this sort of thing.
If you’re worried about coming off like Bob the Builder, consider getting a slightly fuller pair of jeans. Levi’s Vintage Clothing 1947 501s, Orslow 105s, Rubato Lot Nr1, 3sixteen CS-100x, Buck Mason Full Saddle, and Blackhorse Lane NW1 all have a mid-rise, relaxed fit — comfortable but not veering into JNCO territory. Gustin, a pre-order, direct-to-consumer denim brand, offers made-in-America raw jeans for under $100. Their 1968 vintage straight fit channels a mid-20th-century James Dean vibe — grown-up jeans for guys transitioning away from slim denim but not ready to go fully baggy. Vintage Levi’s 501s from the eighties and nineties also have a slightly higher rise and more room in the thigh with a gentle taper (again, call Wooden Sleepers). If you have a hard time finding off-the-shelf jeans that fit, Todd Shelton and Williamsburg Garment Company can make a custom pair.
For something more contemporary, try Lemaire’s twisted leg pants. Pair with chunky knits and an oversized topcoat or one of Auralee’s tops.
Big Outerwear
Outerwear is an easy entry point into roomier silhouettes without a complete wardrobe overhaul.
Take overcoats. You can wear an oversized one with slim jeans and chinos you already own, as well as the fuller fatigues and wool-flannel trousers you might add. The key is to go big — something that falls to your knees or longer adds a sense of drama and verve (think eighties Richard Gere). A long overcoat swishes around your knees when you walk, looks great with a tailored jacket, and adds a bit of sophistication to casual clothes.
Beyond length, consider sleeve construction. A set-in sleeve, with its shoulder seam positioned on the bone, creates a structured, T-shaped silhouette that feels more formal and commanding.
A raglan sleeve, on the other hand, features a diagonal seam extending from the collarbone to the armpit, offering a slightly more casual, rounded shape that layers well over bulkier garments.
Several brands deliver on proportion and quality. Kaptain Sunshine’s Traveler (ed. note: this coat is so gorgeous it is sold out but it should be restocked in the fall), De Bonne Facture’s Grandad, Wythe, Berg & Berg, The Anthology, and Drake’s raglans are among my top picks. Traditional clothiers like O’Connell’s and Ben Silver offer classic overcoats reminiscent of those found in your grandfather’s closet. For more budget-friendly options, check out Spier & Mackay or Cavour. And don’t overlook vintage — classic overcoats were built to last, meaning even decades-old pieces are often in excellent, wearable condition.
If you live somewhere hot, update your bomber jacket with a blouson inspired by mid-century originals. These feature slightly dropped shoulders, a rounder body, and a cropped length. Some of my favorite brands for this style include Monitaly, Document, and Brut. For a more affordable option, Alpha Industries’ heritage-fit MA-1 and CWU 45/P are excellent choices. If you prefer something in denim, trucker jackets from StandardTypes and Lee offer a similar silhouette.
Knitwear
While men’s knitwear tends to be more restrained than women’s (e.g. the sculptural, curved lines of Lauren Manoogian’s pullovers), meaningful variation exists within its narrow confines. Billy Crystal’s legendary cable knit in the 1980s film When Harry Met Sally has voluminous sleeves, dropped shoulder seams, a high neck, and banded hem. Contrast that with former Congressman Matt Gaetz’s hoodie, which is long, slim, and slinky. It simply doesn’t have the same verve.
For a classic Aran sweater, consider O’Connell’s, Aran Sweater Market, or Inis Meáin if you’re willing to splurge. Broadway & Sons offers Royal Navy submariner sweaters with a wide body and tightly knitted hem, allowing you to adjust how they sit on your torso. For a similar silhouette in a hoodie, check out Brut and Bare Knuckles, which make boxier, mid-century-inspired shapes.
When you’re just starting to loosen up, it can take time to appreciate the difference between fit and silhouette. Fit should be narrowly defined — your suit jacket’s collar should sit cleanly against your neck, trousers should drape smoothly, and buttons should fasten without strain. Silhouette, on the other hand, is about the overall shape of your outfit when stripped of details. Not everything has to look like it was put on with a vacuum sealer for it to technically “fit.” By gradually incorporating roomier pieces into your wardrobe, you’ll find a balance that feels right to you.
