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Suiting Up, Dressing Down: 10 essential items that every guy should own

By Diana Yan ‘15  |  april, 2014, Issue 1
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1. Super 130s 100% Wool Suit from Proper Suit; Dress shirt from Hall & Madden
2. Merino Crewneck Sweater from J.Crew
3. Slim Fit Dry Jean from Acne Studios
4. Dress Chino from Club Monaco
5. Dark Brown Leather Belt from Prada
6. Dark Brown Plain Oxford from Cole Haan
7. Cotton Blazer from Thom Sweeney

Dapper. Custom built. Full canvas. Made to measure. Quality. Suits. These words cross my mind as frequently as stock symbols in a ticker stream across CNBC and Bloomberg. Needless to say, I have a crush on menswear. My internship at a custom suit making company that's disrupting traditional suit retailers has only heightened my appreciation for men's fashion and tailored clothing.

In contrast, most guys don't like to shop, and pay little attention to season or occasion, so long as the clothes fit. While that might have worked pre-Booth, it would be wise for dapper Boothies to start investing in a few pieces that can be relied on to build their professional brand. To those guys, the ones who prefer to have a simple go-to guide, I present to you the basic starter kit for suiting up and dressing down as you work hard and play harder in the months ahead:

1. Navy or Dark Gray Wool Suit
For the office, conference or nearby cocktail lounge, this suit helps you fit in wherever you are and still get noticed. Tip: Find a good tailor who understands (or can guide) your fashion vision.

2. Button-Down Dress Shirt
Basic colors: white and pale blue. Wearable with both your dark or light colored suits. A good quality white dress shirt is the most versatile item in your closet and can be worn with a suit, under a sweater or paired with trousers and a statement belt. The blue shirt can be paired with a tie in a darker shade of blue.

3. Tie
A silk woven tie will elevate any suit and dress shirt combination.

4. Accessories: Watch and Leather Belt
The watch can be worn on all occasions. You can look at the time in a more discreet way during, say, a meeting, interview or date without appearing rude by taking out your cell phone. Wear a belt to keep your suit pants up; make sure it matches the color of your dress shoes.

5. Sports Coat or Cotton Blazer
Wear this as a standalone blazer for when you don't feel like wearing a suit but still want to look great. This piece is also perfect for date nights or slightly dressier nighttime social functions.

6. Lightweight Cardigan or Sweater
Cotton, cashmere, or close weave wool. A versatile item that can be worn with almost anything and as a layering piece.

7. Classic Trousers
Slim fit. A good alternative to suit trousers and can be worn with a shirt, shirt and jacket, t-shirt and sweater - the options are endless.

8. Cotton Jeans
Slim fit. Lighter denim for the daytime and darker denim for nighttime.

9. Socks
To keep your feet dry.

10. Shoes
One pair for formal occasions (ex: black leather). One pair for casual occasions (ex: canvas sneakers). One pair for all-purpose / in between occasions (ex: brown leather shoes; suede Desert or Chelsea Boots) that can be worn year round, with jeans or to a formal event.

Bonus: Medium-size travel bag
For the gym and your weekend getaways to the beach, mountains and exotic destinations.

Leading a well-dressed life comes down to wearing clothes with the perfect fit. Clothes that fit do not call attention to themselves, and they make you feel confident and relaxed.

Diana Yan is currently interning at Proper Suit and Hall&Madden, two Chicago-based luxury brands disrupting traditional menswear and retail fashion.

Last Updated 4/9/14
Last Updated 4/9/14