Three Ways to Pull Off a Suit This Holiday Season, All Under $1,000

A little tailoring never hurt nobody

November 13, 2023 10:37 am
A photo of a model in a houndstooth jacket from Madewell on an orange background
There are tons of ways to wear suiting that doesn't suck.
Yeti/Getty Images

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As you may have heard — we’ve only been discussing it, for like, three years — that there’s been something of a tailoring revolution. The total 180 from the stuffy old businessman suits you’d pull out once a quarter for your performance review to a new landscape of relaxed and generally fire options now available for not just the sartorially inclined but for the everyday guy, has been a welcome change. And with this very fact in mind, this season, we’re recommending that you invest some serious time (at least the approximate length of one InsideHook article) in considering a new suit for the holiday festivities.

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Holiday Suiting, Three Ways

The menswear moment: J.Crew Kenmare Italian Moleskin Suit Jacket

The All-American archetype: Buck Mason Italian Soft Wool Flannel Graduate Blazer

The ’90s sitcom suit: Madewell The Roebling Two-Button Blazer

To help you look your very best on Thanksgiving, Christmas, Hanukah or whatever festivities you might partake in, we’ve dropped three presidential pardon-worthy looks, all under $1,000, for you to replicate. There’s a classic menswear two-piece from J.Crew, Americana tailoring, Seinfeld-style sweaters and so much more. Take inspo where you need it, or just copy the whole damn thing. Below, three ways to rock suiting this holiday season.

How to Wear a Suit This Holiday Season

The Moleskin Menswear Moment

Total: $973

When you think of a sartorial-leaning look for the holidays, your mind probably snaps to corduroy. A tried and test option, surely, but why not shake it up? After all, silky moleskin two-pieces, like this Italian-milled duo from J.Crew’s latest holiday drop, add a touch of sophistication to the affair. Pair with some low-key knitwear and an excellent pair of boots, and you’re all but guaranteed to be the best dressed.

The Take Ivy Touchdown

Total: $844

A grey suit is a classic for a reason (because it looks good), but Buck Mason’s latest foray into tailoring has fully captured the spirit of ivy in 2023. The feel of the Graduate Suit might as well be sweats, and the fit — slouchy, but not silly — considers not only the general relaxed vibe we want in our suits nowadays but the sheer amount of festive treats we will be consuming. Toss on a white oxford and a poppy knit tie, like this tobacco-colored silk joint from Todd, to complete the look.

The Seinfeld Shake Up

Total: $1,032

Okay, we admittedly cheated with this one. Not only is it a smidge over $1,000, but it’s not a suit either. But hopefully you’ll afford us the grace to explain as you remember how wild some of those ’90s sitcom fits went (RIP Matthew Perry). Pairing a relaxed, over even oversized, blazer with light wash jeans is a tried and true combo, and with the right accoutrement, can be a smash hit at whatever holiday party (or hot date) you’re blessing with your presence.

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