Everything You Need To Know About Styling Your Guy

Surely it's happened to you: a fellow in your life—maybe a buddy, perhaps a boyfriend—asks you for wardrobe help. As he should, of course, since you're stylish, chic, and perfectly put together. But just because you've figured out your own look doesn't mean you can instantly assemble his. Menswear is its own beast, which is why we've compiled this styling and shopping guide for you.

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    From where a tie should hit to most important thing to know when buying a suit, we've got tips and tricks galore from some of the most influential fashion insiders. Read on for our crash course in dressing dudes; we promise you'll learn something (or at least be entertained).

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    Meet The Experts

    1. Ilaria Urbinati: Stylist (dresses Armie Hammer, Bradley Cooper, and more). She's also the co-owner of LA's beloved menswear store Confederacy.

    2. Jenny Ricker: Stylist (dresses Joseph Gordon Levitt, Zac Ephron, Aaron Paul).

    3. Will Welch: Senior Editor, GQ

    4. George Esquivel: Designer, Esquivel Shoes and creative director, Tumi.

    5. Estee Stanley: Stylist (dresses James Marsden, Vince Vaughn, and Luke Wilson, and many others). She's also an interior designer, editor-at-large for Domaine, and co-creator of HomeMint with Justin Timberlake.

     

     

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    PHOTO: GG/Fame Flynet Pictures
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    Sneakers

    The key here is to keep it simple. "If you are down to spend a chunk of cash, try Common Projects," GQ's Welch says. (Urbinati agrees, though she suggests the classic low-top in white, while Welch prefers gray.) For less pricey options, classic Jack Purcells or Chuck Taylors will work.

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    PHOTO: fashionbeans.com

    Dress Shoes

    Oxfords are the name of the game here: Urbinati likes Ferragamo for a dressier shoe, while Ricker goes for a thrify thrill. "Mr. B's x Aldo has well-made brogues that won't break the bank," she says. Esquivel recommends a leather-sole suede shoe because it works for both casual and dress-casual situations.

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    Ankle Boots

    "Boots are a choose-your-own-adventure situation," Welch says. "Stylistically speaking, do you identify more with a construction worker, an architect, or a punk?"

    Bonus Suggestions
    "A pair of white Adidas Rod Lavers (with either blue or green accents) is sort of the GQ go-to." –Will Welch

    "I love Rachel Comey's casual tan lace-ups in the summer with no socks and rolled up chinos." –Ilaria Urbinati

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    PHOTO: Photofab/Rex/Startraks Photo

     

     

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    Raw Denim

    "Every dude should have a slim, raw jean he can break in himself like a big boy--none of this faux broken-in business," Urbinati says, and our other experts agree. While Urbinati and Stanley like A.P.C.'s timeless raw denim ("No matter if you're tall, thin, short, or stocky--their fit is amazing," Stanley says."), Esquivel and Welch both swear by Baldwin Denim's medium rise, slim fitting The Henley Jean

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    PHOTO: fashionbeans.com

    Classic Denim

    The classics are always good, too. "If you want to look great and like you know what's up, but you kind of hate it when people ask you about your clothes, go with Levi's 511s," Welch says. "You can buy three pairs in blue, black, and white for less that what all these denim-nerd brands are charging."

    Bonus Suggestions:
    "J Brand's Kane Jean is the perfect slim-straight jean." –Ilaria Urbanati

    "J Brand's Tyler Jean is not-too-skinny slim jean for guys with long, lean legs." –Ilaria Urbanati

    "Whether his style is preppy, rocker, or classic, he can never go wrong with a vintage Levi 501." –Estee Stanley

    "Nudie Jeans Co.'s dark denim is best for dressing up an otherwise casual look." –Jenny Ricker

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    PHOTO: FilmMagic/Getty Images

     

     

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    While khakis sound awfully fratty, there are apparently some cool chinos out there. "Dockers, which used to be a punchline--shorthand for slouchy, pleated American style--has introduced a fit called the Alpha that's very tapped into what stylish guys are wearing now," Welch says.

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    PHOTO: alexandergrant.blogspot.com

    Urbinati recommends Gant as well as Shipley & Halmos for chinos, while Ricker likes J. Crew's broken-in slim fit and classic versions.  

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    Bonus Suggestions

    "Other favorites are UnisRRL, and an amazing Italian brand called Closed. Closed does really great slim cargo pants too." –Will Welch

    "Rag & Bone chinos are a must! So good in classic khaki or navy." –Estee Stanley 

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    PHOTO: GG/Fame Flynet Pictures
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    PHOTO: hespokestyle.com

    Denim Jacket

    A classic jean jacket is a must-have for Ricker and Stanley. "It should be a staple in every man's wardrobe," Stanley says. 

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    Leather Jacket

    Just like the ladies, a well-dressed man needs a leather jacket. "Everyone from Schott, who made the Perfecto jacket that Joey Ramone wore, to Saint Laurent has insanely badass versions," Welch says. 

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    Bomber Jacket

    Urbinati likes a bomber, specifically either a Gucci's leather version for colder days, and a cotton or lightweight option for warm weather. "It's usually best to go down a size on a bomber, as it should look slightly shrunken," Urbinati says. "If it's even a little too big, the look is ruined." 

    Bonus Suggestions:
    ​"An unstructured blazer is also a staple to have to for those last minute garden party situations." –Jenny Ricker

    "A good all-around jacket that is available from all brands, in many price points, is the utility jacket." –George Esquivel

    "I love a Diesel leather jacket; I go for the simplest ones with no bells or whistles." –Ilaira Urbinati

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    PHOTO: WireImage
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    Fit

    When it comes to suits, our experts agree: the jacket has to fit perfectly, or else you might as well stay home. "The shoulders of the jacket need to hit right at the peak of your shoulders and hug them snugly," Welch says. "If the shoulders don't fit you perfectly, you've got the wrong size, and no amount of tailoring is going to fix it." Everything else--specifically, the body and the sleeves--can be easily adjusted to fit. 

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    PHOTO: fashionbeans.com

    Style

    Style-wise, Urbinati votes for Burberry's slim two-button suits in gray (the most versatile) or navy, but also suggests trying something in a color like burgundy or green. Once a suit's been picked, make sure that sleeve length is perfect. Welch says the jacket shouldn't cover up any of your hand at all, so you'll show approximately ¼-inch of shirt cuff, while Urbinati prefers a ½-inch of shirt to show.  Also worth noting: material. "The big thing is dressing seasonally," Welch says. "You don't have suits you wear year-round; you have three fall-weight suits and three summer-weight suits. It just makes sense." 

    Bonus Suggestions:
    "Have your tailor nip the jacket in at the sides to give you broad shoulders and a slender waist. You're not supposed to say this in terms of men's clothes, but eff it--that V shape is how you get what's known as sex appeal." –Will Welch

    "My pet peeve is a too-long jacket--the old rule of putting your arms straight down and being able to curve your palm around the bottom of the jacket is dated. It should come up higher than that." –Ilaria Urbinati

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    PHOTO: FilmMagic/Getty Images
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    PHOTO: fashionbeans.com

    Fit

    Just like with suit jackets, finding a dress shirt that fits a fellow's shoulders perfectly is imperative. The neck must fit properly too; sleeve length and the width of a shirt can be easily tailored, the rest, not so much. Also pay attention to the collar. Welch likes a smaller collar: "Preferably a semi-spread, which means it's not just the classic point collar with tips pointing down at your shoes, but it's not an outrageous spread collar that makes you look like a Wall Street wannabe.

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    Shopping & Suggestions

    Welch likes Hamilton or Sid Mashburn, while Urbinati likes Dior Homme (in white or pale blue) for "smaller dudes," and Dolce & Gabbana for a slim-fit shirt that works on a bigger build. Less expensive options abound too. Topshop makes some Urbinati-approved options, while Ricker suggests J. Crew and Esquivel recommends Uniqlo's affordable slim-fit shirt.

     

    Bonus Suggestions:
    "For most shirts, I usually have the tailor add darts in the back to slim the torso--especially for broad shoulders." –Ilaria Urbinati

    "Make sure the collar isn't too big or too pointy--that's the quickest way to look dated." –Will Welch

    "My advice is to opt for the cheaper shirt, and spend a little extra to have it tailored to fit perfectly. It will assure you look like a million bucks without having to overspend." –Jenny Ricker

    "Always white or periwinkle blue and 100% cotton--never silk!" –Estee Stanley

     

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    PHOTO: Goodwin/Fame Flynet Pictures
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    PHOTO: meninthistown.com

    The perfect t-shirt is an elusive thing, but start your hunt at Gents. "They make that '50s James Dean/Marlon Brando cut--shorter in the body and the sleeve," Urbinati says. 

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    Welch also likes tees with a shorter arm, specifically ones by Ralph Lauren Black Label Denim, which he calls the perfect pocket t-shirt. "The colors are really inky--they look almost wet," he says. For less rarified options, he also like J. Crew's pocket tees in washed out colors. Also affordable: Urbinati's favorite crewneck from Alternative Apparel. As for colors, make sure he has the staples: black, white, navy, and gray. 

    Bonus Suggestions:
    "If you're a little more fashion-y, try James Perse, who makes a really great jersey crewneck tee." –Will Welch

    "Todd Snyder makes good tees in colors that read cool and vintage." –Ilaria Urbinati

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    PHOTO: Getty Images
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    Much like with socks (more on that in a minute), a casual belt can show a little personality. "This is a great place to add a pop of color: greenblue, or red," Urbinati says. Or if you're feeling like really showing some summertime flair, Welch allows that a ribbon belt with a ring buckle is a good option for seersucker pants, Bermuda shorts, or khakis. "It's a preppy staple, but you don't have to look like your mother is a Tom-Collins-addicted bottle-blond named Miffy who summers on the Cape," he says. "It'll also look cool in Arizona, or Louisiana, or St. Paul." For a dressy option, Ricker recommends a leather belt from Hermes. "It's a little more expensive," she says. "But it's also reversible, so you're getting two belts for the price of one."

    Bonus Suggestions:
    "A black leather belt with silver hardware and chocolate leather belt with antique gold hardware are no brainers." –Estee Stanley

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    PHOTO: ChinaFotoPress/Getty Images
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    Length and Width

    When it comes to ties, our experts agree: it should graze the top of the pants. Width, on the other hand, is up for debate. Urbinati says the width of the tie should be in proportion to the lapel of the suit jacket. Ricker thinks it's more about the guy's build, meaning broader men do better in wider ties, slimmer men in skinny ties. Welch and Stanley both think a tie that's 2 ½-inches at its widest is ideal. 

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    PHOTO: alexandergrant.blogspot.com

    Shopping & Suggestions

    As for brands, Urbinati likes Rag & Bone, Band of Outsiders, Burberry, J. Lindeberg, and Gentry. If you're on the hunt for something a little more obscure but equally awesome, Welch suggests Alexander Olch ties.

    Bonus Suggestions:
    "You should have some cotton ties for when it's hot out and wooly ties for when it's cold." –Will Welch

    "I love the selection at Barneys. They have ties ranging from playful to conservative and from $50-$500." –Jenny Ricker

     

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    PHOTO: Getty Images
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    Having a strong sock game is just one more way a fellow has of showing his sartorial abilities, so finding the right ones is imperative. With all the shorter hems on trousers these days, it's nice to have something to show off, like a thin or thick stripe, floral, or gingham print Urbinati says. If a statement sock isn't for you or you're simply looking for a simple dress sock option, try Calvin Klein, which Urbinati swears are affordable and super soft. Ricker also likes hand-made socks from British brand Pantherella.

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    PHOTO: Getty Images

    Bonus Suggestions:
    "The best socks I've ever purchased are Falke from Douglas Fir in Los Angeles. They always have a great selection." –George Esquivel

    "I hear Happy Socks is good for colors and patterns and getting your footwear ya-yas out." –Will Welch

Shop this Story
Original Achilles Leather Low Top Sneakers

Original Achilles Leather Low Top Sneakers

Common Projects, $320
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Tournament Suede Sneakers

Tournament Suede Sneakers

Common Projects, $320
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Jack Purcell Sneakers

Jack Purcell Sneakers

Converse, $60
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Chuck Taylor All Star Sneakers

Chuck Taylor All Star Sneakers

Converse, $50
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Cap-Toe Oxford

Cap-Toe Oxford

Salvatore Ferragamo, $640
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Cap-Toe Oxford

Cap-Toe Oxford

Salvatore Ferragamo, $640
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Theatum Brogues

Theatum Brogues

ALDO, $175
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Kris Suede Shoe

Kris Suede Shoe

George Esquival, $600
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875 Moc Rubber Soled Leather Boots

875 Moc Rubber Soled Leather Boots

Red Wing Shoes, $220
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Desert Boot

Desert Boot

Clarks, $120
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1460 Boots

1460 Boots

Dr. Martens, $120
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Originals Sneakers

Originals Sneakers

Adidas, $48
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Uncle Dan Oxfords

Uncle Dan Oxfords

Rachel Comey, $338
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New Standard Jeans

New Standard Jeans

A.P.C., $185
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The Henley Jeans

The Henley Jeans

Baldwin, $165
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Kane

Kane

J Brand, $154
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Tyler

Tyler

J Brand, $196
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Vintage 501xx 1966 Jeans

Vintage 501xx 1966 Jeans

Levi’s, $215
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Thin Finn Jeans

Thin Finn Jeans

Nudie Jeans Co., $199
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Alpha Khakis

Alpha Khakis

Dockers, $59
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Broken-In Chinos in Urban Slim Fit

Broken-In Chinos in Urban Slim Fit

J.Crew, $70
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Essential Chuno in 484 Fit

Essential Chuno in 484 Fit

J.Crew, $70
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Canvas Chinos

Canvas Chinos

Gant, $165
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Belmont Pants

Belmont Pants

Shipley & Halmos, $195
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One Star Perfecto Leather Motorcycle Jacket

One Star Perfecto Leather Motorcycle Jacket

Schott, $900
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Slim-Fit Leather Biker Jacket

Slim-Fit Leather Biker Jacket

Saint Laurent, $4900
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Burgundy Washed Nappa Leather Jacket

Burgundy Washed Nappa Leather Jacket

Gucci, $2700
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Lumi Leather Jacket

Lumi Leather Jacket

Diesel, $898
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Cotton-Blend Bomber Jacket

Cotton-Blend Bomber Jacket

PS by Paul Smith, $179
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Lightweight Bomber Jacket

Lightweight Bomber Jacket

Neil Barrett, $500
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Washed-Denim Jacket

Washed-Denim Jacket

J.Crew, $140
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Bruno Twill Jacket

Bruno Twill Jacket

Haberdash, $599
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Khaki Lakeville Jacket

Khaki Lakeville Jacket

Penfield, $185
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Modern Fit Wool Suit

Modern Fit Wool Suit

Burberry, $1195
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Slim Fit Wool Mohair Suit

Slim Fit Wool Mohair Suit

Burberry, $1295
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Suit

Suit

Albert Hammond Jr. for Confederacy, $2125
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Selected Homme Green ‘Walton’ Suit

Selected Homme Green ‘Walton’ Suit

Topman, $280
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Embroidered Cotton Poplin Shirt

Embroidered Cotton Poplin Shirt

Dior Homme, $530
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Bee Embroidered Striped Poplin Shirt

Bee Embroidered Striped Poplin Shirt

Dior Homme, $530
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Gold Fit Shirt

Gold Fit Shirt

Dolce & Gabbana, $365
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White Double Cuff Long Sleeve Smart Shirt

White Double Cuff Long Sleeve Smart Shirt

Topman, $56
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Secret Wash Point-Collar Solid Shirt

Secret Wash Point-Collar Solid Shirt

J.Crew, $65
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Men Slim Fit Long Sleeve Shirt

Men Slim Fit Long Sleeve Shirt

Uniqlo, $30
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Short Sleeve Crew Neck T-Shirt

Short Sleeve Crew Neck T-Shirt

Gents, $38
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Short-Sleeved Pocket T-Shirt

Short-Sleeved Pocket T-Shirt

Ralph Lauren, $85
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Broken-In Jersey Tee

Broken-In Jersey Tee

J.Crew, $25
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Crew Neck Cotton-Jersey T-Shirt

Crew Neck Cotton-Jersey T-Shirt

James Perse, $45
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Grey Heather Crew Neck T-Shirt

Grey Heather Crew Neck T-Shirt

Todd Synder New York, $70
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Washed Webbing Belt

Washed Webbing Belt

Gap, $25
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Contrast Edge Striped Webbing Belt

Contrast Edge Striped Webbing Belt

Gant, $price upon request
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Red Smart Leather Belt

Red Smart Leather Belt

Topman, $32
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D-Ring Belt

D-Ring Belt

Sid Mashburn, $55
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Cape Cod 32 Belt

Cape Cod 32 Belt

Hermes, $890
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Knit Bar Stripe Tie

Knit Bar Stripe Tie

Rag & Bone, $59
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5cm Silk Jacquard Tie

5cm Silk Jacquard Tie

Band of Outsiders, $157
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Stripe Detail Silk Tie

Stripe Detail Silk Tie

Burberry, $195
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Lalle Vintage Stripe Burgundy Tie

Lalle Vintage Stripe Burgundy Tie

J. Lindeberg, $90
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Sky Blue Multi-Stripe Socks

Sky Blue Multi-Stripe Socks

Paul Smith, $35
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Highland Socks

Highland Socks

Shipley Halmos, $30
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Highland Socks

Highland Socks

Shipley Halmos, $30
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Multi Stripe Socks

Multi Stripe Socks

Gant, $11
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Bamboo Blend Flat Knit Dress Socks

Bamboo Blend Flat Knit Dress Socks

Calvin Klein, $14
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EXPLORE: How To, Ilaria Urbinati, Will Welch, Estee Stanley, Jenny Ricker, How To, menswear, George Esquivel
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