Fashion Tips for Short Men feat. Dennis Thompson

April 14th, 2014

Similar to our friend Waraire Boswell, Philadelphia native Dennis Thompson got into custom tailoring out of necessity.

At 5’5″ 125 lbs, everything off-the-rack was way too big and provided no shape. Dennis studied fashion design at the Art Institute in Philadelphia, followed by fashion merchandising at LIM in NYC – “I thought it was important to understand both sides of the business”. He then started to dabble in the MTM tailoring business, and quickly found his niche.

“I got really interested in suiting when I was interviewing for jobs after college.  I could never find anything that fit me properly because of my size, so I thought, why not just make it myself? My first internship was with the stunning menswear-clad Amber Doyle at Doyle Mueser. As with any on-the-job training, they taught me many things that couldn’t be taught in the classroom.

One day I was leaving my internship and ran into designer Thom Browne himself (only in NYC, right?). I introduced myself, gave him my pitch, and a month later I was heading up the TB Made-To-Measure program. From there I eventually moved to Bond Street to work with My. Grayson Knight at Billy Reid.

More recently, I’ve decided to take the plunge and venture out on my own.  Starting my own label has always been a dream of mine, and now I have the opportunity and confidence to do it.”

With years of experience in MTM suiting, Dennis has certainly learned more than a thing or two about tailoring for a small frame. Here’s a taste of his sharply tailored personal style, along with some of his advice for flattering a smaller physique.

1. Trim the Fat


“For a small guy it comes down to this: you need a good tailor. For someone like myself, at 5’5”, nothing will fit me off-the-rack. The only place that comes close is Thom Browne (his brand is geared toward small, slim guys).

The first rule is make sure it fits your shoulders, as that is the most expensive and difficult alteration. Next rule I have is slim your pant, considerably [like my boy Adam Lampell, who wears his suit trousers like skinny jeans – Dan].  This will elongate your physique and make you appear taller from a distance (nothing helps when you’re standing next to tall people).

When you’re smaller it’s all about proportion. You don’t need anything extra… Get the ‘fat’ out of your clothing.”


Suiting tips for small guys:

  • Skinny ties are your friend.
  • Make sure the button-stance of your jacket hits at the smallest part of your midsection. This way you can cut the jacket as narrowly as possible with minimal fabric pulling.
  • It’s okay to wear a slightly cropped jacket that doesn’t quite hit the crotch line, and hardly covers the seat
  • Sleeve and pant length are critical. Show 1/2″ of cuff or more, and go with minimal break.
  • Dark colors are slimming, and slimming = lengthening.

I love the subtlety of the colors in this charcoal glenplaid fabric.

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Gray Autumn Glenplaid Suit

  • Blue stripe shirt by Billy Reid Custom ·
  • Tie by Thom Browne ·
  • Vintage lapel pin (father’s) ·
  • Vintage ring (father’s) ·
  • Loafers by Cole Hann (Vintage)
  • · Charcoal Glenplaid Three-Piece Suit

2. Update Thy Waistcoat


“Whenever I have suits made, I almost always order a waistcoat as well.

In my opinion it’s one of the most underrated things you can do if you’re smaller in stature. It adds a more streamlined silhouette if you take off your jacket (showing the full pant line). It also it keeps you a little more formal.”


A waistcoat should just cover the waistband. No shirt showing between the vest and pants!

Notice the deeper neckline of this waistcoat, and the tight spacing of the (only) five buttons. Also note the slimmer shoulder width.


I was supposed to keep this secret – but these are womens chukka boots. One of the advantages of being smaller in size is that you can shop the women’s and children’s “menswear” sections – both of which are usually cheaper too.


Donegal Tweed Vest in Monochrome

Blue Bengal Stripe Oxford Shirt

3. Best-Fitting Foot Forward


“My style varies a lot, but typically in NYC I’m wearing a suit. If not a full suit, a blazer or jacket is a must.  I try to be put-together whenever I walk out the door…in a city like NY you never know who you might randomly meet (that’s how I got the job at Thom Browne). It’s part of the excitement of the city.

I don’t really have a particular style icon, but I always look to Mr. Nick Wooster and Mr. George Cortina. They are at both ends of the style spectrum; Nick is fashion and expression, George is classic and elegant. What ties it all together is they both understand that fit is the number one priority in dressing with style.”


When it comes to overcoats, make sure it’s narrow through the shoulders, slim through the body, and doesn’t hit past the knee.

Mid-thigh is an ideal length, like Dennis’ cotton topcoat here.


Glenplaid Performance Wool Suit in Navy

  • Sunglasses by The Row ·
  • Cotton scarf by Billy Reid ·
  • Cotton topcoat by Thom Browne ·
  • Pink banker collar shirt by Billy Reid custom ·
  • Polka dot slim tie by Billy Reid ·
  • Vintage ring ·
  • Wingtips by To Boot NY
  • · Navy Shadow Plaid Three-Piece Suit

4. Let’s Talk Trousers


“Pant Length. I know this is a touchy subject with some people, especially in the blog world… I started aggressive and dove right in. I went from full-on Thom Browne two-inch cuffs that hit six inches above my shoes, and gradually got to a more traditional (and professional) very-slight break.

For a shorter guy this is probably the single most important element (along with a slim taper) that can help make you look ‘taller’… I like something that has almost no break and just kisses the top of my lace ups. On a loafer it can look little shorter (especially those with an old school low vamp – which I prefer).”

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Charcoal Essential Suit

Blue USA Oxford Shirt

5. Proportional Accessories


“Jacket Length. Should hit right at the bottom of your ass, or slightly higher [it really depends on the size and shape of your abdomen and hips].

I have played around with my jacket length for some time now and I think I finally have it down to what I feel works best. You want something that keeps the eye line flowing from jacket to trouser – lengthening the leg line without making the jacket look noticeably chopped or awkwardly proportioned.”


Your a smaller guy, so your accessories should be smaller too.

Notice the tiny tie bar here, on a skinny 2″ tie.

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  • Sunglasses by The Row ·
  • Custom Blue Plaid Suit by Billy Reid ·
  • Blue striped Dress Shirt by Billy Reid ·
  • Grey Plaid Tie by Thom Browne ·
  • Tie Clip by Thom Browne ·
  • Chocolate Suede Double monks by Alfred Sargent

Thanks for reading, and special thanks to Dennis for participating!

Yours in style,

Articles of Style

Photography by Alex Crawford and Westley Dimagiba

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