I believe in dressing for success…But how?

Grew up in a small town in the Midwest. I ended up taking a scholarship at a local state school. I worked hard during undergrad and was able to land at a solid MM shop base in the Midwest. I always told the story of "I want to be close to family" and "this is where I grew up" to get the job but that was a lie; I just wanted IB. Now I have been at the desk for a year (ignore username) and am realizing I want more.

I just finished taking the GMAT, and now I am trying to lateral to NYC. All my life, I have been the "Midwest kid," but now I want to dress to impress! When I talk to other analysts/associates, I always feel lesser. They are just more polished overall than me. They dress better and they hold the floor when speaking. As the title says, I believe in dressing for success. Look good, feel good type stuff. I think first impressions matter and I obviously don't have "it." What are the key things I need to do to take my looks to the next level? Honestly, I want to look like a Harvard MBA that just finished up at a MF.

I am also frugal, so I assume that plays a role in it. This fall I have set aside 5k-8k to do a whole fashion update. Would love WSO's fashion advice! what brands? what to buy first? maybe do teeth whitening? Maybe buy better glasses? Any advice is welcome.

This is a serious question. Thanks!

Comments (29)

nutmegger189, what's your opinion? Comment below:

Holding the floor is only half about your appearance. I don't really subscribe to the same view as you, some of the most successful people I've met go to work in a polo and jeans. They hold the floor with their actual product and general vibe.

But we can go with your view for now. By no means an expert here but I don't think anyone can argue that a well-tailored suit (and even tailored shirts) are a staple for looking like "1 million bucks" in the workplace. Doesn't have to be the most expensive thing in the world. Navy works well. The fit and the materials are what matter most. Then some nice, shiny black leather shoes and you're golden.

RuckSack, what's your opinion? Comment below:

If you feel successful, you'll act successful. There's no shame in using clothes to achieve greater self worth. 

Fit is more important than just buying top brands. Tailoring is great or if you can get a personal shopper/stylist session they can help with sizing if you're buying off the peg.

Boss Guides currently has some good information on suits styling or have a search for Ralph Lauren Ready to Wear if you fancy some contemporary inspiration.

Best of luck out there and I hope you land the NYC position!  

krn.nfltn, what's your opinion? Comment below:

For shoes: Crockett & Jones, Tod's, Ferragamo, Edward Green and John Lobb are your new best friends... Just don't forget the shoes trees and care 

Most Helpful
Five Star Man, what's your opinion? Comment below:

Don't blow all of that amount at once. Buy a few nice items and ease into them. Then you can continue to build.

For suits, agree with the other poster, find a solid tailor. That will help it look good on your body type. Stick to navy and charcoal to start. Grab a sport coat or two, so you have that business casual look locked in.

For shirts, I use proper cloth, again slightly more tailored to body type.

Shoes, get a few nice pairs, but keep them relatively conservative. 

Haircut, start getting professional haircuts or find a great barber (I just moved and the new guy fucked up my hair, ruined my entire week).

Always match belt to shoes and socks to pants. 

Conservative always wins, so no gaudy logos or silly colors. Definitely no pocket squares and keep cuff links to a minimum. Monograms are probably okay (though I see them less) as long as they are understated.

Invest some money, or go on YouTube, and find professional speaking courses. You'd be surprised how much more confident you are and how much of a skill public speaking is.

Diversify your interests, so you have a lot of different things to talk about and reference. You'll become a more interesting person. Buy an Emily Post book, so you can learn the right etiquette for social situations. Nobody likes boorish behavior. You'll also feel more comfortable at a formal dinner.

Most of "holding a room" is confidence. People look good because they feel good about themselves. So practice, go to lower risk environments and talk to people. 

Drop the MM and Midwest chip on your shoulder, you are who you are and it's gotten you to where you are now, be proud of your work ethic - stop comparing yourself to a MF or a Harvard MBA (outside of this forum, they aren't comparing themselves to you).

"Look good, play good. Play good, get paid good." - Deion Sanders 

ADTIBE, what's your opinion? Comment below:

Still wear ties on the daily (except Fridays or when meeting with certain clients). Genuinely enthusiastic about neck ties (colors, patterns, dimensions, fabric, etc.). I think people know I like wearing ties so I don't come off as a "try hard". Otherwise the knot, length and matching will be off. People can sense vibes, good or bad.

Since many, including execs, have gone hipster (some forcefully) and ditched ties, it definitely helps me stand out in a unique way. Easy "signaling" hack without much work, risk or investment. BUT, my deliverables are also top notch, so there's a positive correlation (i.e. not trying to cover up subpar performance with a sharp look). NOTE: if your work isn't excellent, dressing well in any regard can backfire and have the opposite effect.

Before or after work, people definitely treat you differently-- usually better. For those that think ties are pretentious, out of style/touch or uncomfortable, there's probably a logical explanation. It could be that certain people are just control freaks, insecure or jealous; if you have a supervisor that fits the bill, you have to understand how to read people. If a higher-up is being petty about something as minor as you wearing a tie, time for you to rethink your career choices and trajectory. Feel free to reply and I'll share my experiences.

People have been talking about the death of ties for literally a century, yet, when it goes out if style enough, it becomes hipster to start wearing them again, so the pendulum swings just as with most things in fashion, finance and the world. 

If you don't want to wear ties voluntarily, then DON'T. Not trying to change anyone's mind, so please don't try to change mine; just sharing my first-hand, real world experience with the OP and anyone else who cares.

  • Analyst 1 in IB - Cov

I think it's a good idea to wait a bit for all the sales before going in too hard.

Allen Edmonds currently has a sale on shoes, and that's certainly a dependable classic. Meermin isn't currently on sale but has been very popular in previous posts, and are like half the price of AE anyways. I've heard about Beckett Simonon but have never worn any. If you're willing to go pricier, Carmina is wonderful. As you're starting out, go oxfords, black. Think Meermin's cap toe or AE Park Avenue. Shoe brands always offer belts that match, so would probably go with a matching belt from whichever brand you choose.

For suits, can't ever forget Suit Supply. I also like Brooks Brothers and Ralph Lauren. Highly recommend this WSO thread on suits. Charcoal and navy suits to start.

Dress shirts, I adore Brooks Brothers, but many people also like Charles Tyrwhitt. Have even heard Nordstrom and Bonobos but I haven't tried those, so would love to hear from anyone who has.

Pants, at least in my office, goes hands down to Lululemon. Try their Commission pants, more dressy than the ABC pants. 

Coats depends a lot on taste. Lots of different styles, from more dressy overcoats with Suit Supply/RL/Brooks Brothers to winter gear from North Face/Arcteryx. I prefer the former, but it doesn't really matter. Would go with something cheaper simple and dependable. Navy or black. 

Now the extras. A good scarf and pair of touchscreen gloves are huge. For socks, I prefer Ralph Lauren. You could also go for Icebreaker or Darn Tough, as they're more expensvie but have lifetime warranties are known to be excellent. Pick up one or two ties from wherever you get your dress shirt or suit, keep them simple and classic stripes and colors.

TechBanking, what's your opinion? Comment below:

Bonobos are great. Charles Tyrwhitt is a great value…I always liked their shoes. Thomas Pink is similar and better at a higher price. Brooks Bros is perfectly fine. Don't be afraid to ask for help from the people at the store. Honestly, most of my button down shirts these days are just from J Crew. 

  • 2
Ehmerica, what's your opinion? Comment below:

Looking sharp absolutely helps you feel better and perform better. Also, people just look at you differently. Nearly every major city has somewhere that you can get made to measure or bespoke which will fit you much better and likely be better than off the rack. These places are not mens wearhouse they are likely mom and pop. Plus, the experience of picking fabrics, buttons and different cut options is great as well.

For shoes you can never go wrong with Allen Edmonds - they will actually get something that fits you well in their stores. On top of it simple maintenance like polishing can help them run for decades with some redrafting every few years.

$8K should be more than enough to get a damn fine wardrobe going, particularly if you leverage sales. TBH, I'd cut it down to 4 and cut the rest. Then add as your career grows.

Also, as someone pointed out working out helps. Add in a positive attitude and you will be fine.

For presenting the key is rehearsal. Know your deck well, plan what you'd like to show and be able to explain the key points clearly. It never hurts to plan out the speaking points with anyone you're presenting with. When you've done several you will need less reversal, but as markets move and needs change it is good to stay sharp and on point. A critical point to remember is that your audience may not understand certain areas like you do so being able to explain rationale in lay man's terms is critical.

Finally, it is beneficial to be able to communicate and relate to those who drink champagne and those who drink Budweiser.

Only two sources I trust, Glenn Beck and singing woodland creatures.
  • 8
IhateKetchup, what's your opinion? Comment below:

Honestly just stay in shape and be a sigma like Patrick Bateman. You will get more compliments wearing a cheap suit that fits good than trying to impress with a expensive wardrobe.

  • Analyst 2 in IB-M&A

OP here. After posting, I realized my position was wrong, so I changed it to the correct title, A2. Original post wont let me edit it, but I am the poster.

I appreciate the comments and feedback. Shout out to everyone helping me. I want to make a few more comments and reply to a few posts here. 

1) Again, great feedback from everyone! A follow-up question to the WSO community. These messages were focused on work, and I do all right at work. I have the Patagonia vest, Charles Tyrwhitt, with the ABC pants, but it is more outside of work where I fail (hard). For example, an old co-worker invited me for beers with his wife and a few of his co-workers (all from reputable PE shops). My dress options were 1) a T-shirt and shorts or 2) work attire. I showed up with #2 and got some crap for it. Not too bad but still not the best look. How do I find a middle group when dining/hanging out? That balance has been tough for me to find. At work, I work hard and get my shit done. No one complains, and everyone likes me, but as soon as we go out, I get weird, can't hold the floor, and never feel dressed "right". Opposite is true as well, I dress too far down at times.

2) [Five Star Man] Great post. I appreciate it. I have been in finance long enough to know the right investments pay off. I am going to invest in myself and buy a course. While looking for a public speaking course, all I could find was Tony Robbins or other guru-type stuff. Would you happen to have any recommendations? Should I look into the executive coach-type classes? Appreciate the other insight. Bought new vejas shoes, got a new haircut (still trying to figure this out), and love the Deion Sanders quote. Finally, your right, I got myself here and I deserve to be here. Imposter syndrome can be difficult smh.

3) ADTIBE I agree with you. Love the tie. I will rock it till I die.

4) Ehmerica Love the rehearsal point. Something I should do more of. I tend to ramble when a curveballs come my way. What are your thoughts on that? Is that just knowing your stuff? or do you have any tips to act polished when you have no clue but are on the spot? 

Finally before everyone crushes me, saying "get your own style, don't ask the internet" or "you're lame to ask WSO! Just buy whatever you want. You are just going for a beer". I would like to say, I have my style but I recognize my style of baggy shirts and shorts (street style) doesn't always come off as presentable or polished. I want to change that to progress my career. I really want to get polished before I head off to NYC. (update on that: I am in a final round interview for a NYC bank)

Grid, what's your opinion? Comment below:

Join a local Toastmasters organization and read Alan Flusser's "Dressing the Man: Mastering the Art of Permanent Fashion "

Outsiders, what's your opinion? Comment below:

In a similar spot of missing the upscale causal between college bar attire and work attire take my advice with a grain of salt.

I have had success with dressing down work outfits by swapping dress pants with jeans/chinos and swapping dress shirts with an untucked Oxford/polo or a plain dark t-shirt. Similar with shoes. Swap the oxfords with a more casual loafer or chukka boot. Basically, the idea is the take a step down in formality in shirt, pants and shoes. You could only do this with 2 of the 3 or even 1 of the three depending on the level of formality of the gathering.

Start here then layer on vests, pullovers or a blazer/coat depending on weather and event.

Again, I struggle with this too coming from a similar background. Happy to get other opinions.

TheBuellerBanker, what's your opinion? Comment below:

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