Jeans 101: Tips on Fit, Brands, Color

Some have described jeans shopping as “soul crushing,” “self-esteem destroying,” “masochistic,” and “terrifying.” How many times have you been lured into a store by a sign reading “JEANS: 50% OFF,” only to leave the store’s dressing room practically in tears after trying on a pile o’ unflattering denim?

Well, this jeans primer is not going to change the fact that designers mass produce clothing for body types that are unattainable to the majority of us.  It is also not going to change your body type. But, it will outline some basic “jeans 101” so that you have some foundation when you are diving into the process of finding a perfect pair, especially in a market that now has an overwhelming number of cuts and styles.

dapperQ He Said/We Said model Tiq Milan rocks Levi’s. Photo by Vito Fun.


Many brands will have sizes that read something like “34×32.” The first number corresponds to your waist measurement. The second number corresponds to your inseam measurement. So, I guess it’s sorta important to know your waist and inseam measurements, no?

How to measure your waist:

    1. Measure around where you normally wear your pants (e.g., about naval level or at the top of your hip bone).
    2. Put one finger between your body and the tape measure to allow for seating and “eating” room.

How to measure your inseam:

    1. Remove your shoes.
    2. Measure your inner leg from the lowest part of your crotch to your foot (bottom of the ankle).

*Vanity Sizing Alert: Esquire Magazine’s article “Are Your Pants Lying to You: An Investigation” reveals some of the waist size disparities between popular brands. Take a few different sizes in the dressing room with you, because the sizes on the labels may be deceiving.

Via Esquire

Some dapperQs prefer the fit of women’s jeans (e.g., “boyfriend,” “straight leg,” and “skinny” cuts). However, women’s jeans are often sized with an arbitrary, single number, such as size “6”. There is no industry standard for women’s jeans sizing, meaning there is even less consistency across brands. While some women’s jeans do have sizes that correspond to your actual waist and inseam measurements, you should be prepared to accept that jeans with arbitrary sizing offer less choice regarding your specific inseam measurements; at best, these jeans may come in short, regular, or long. Do your research beforehand. Most retailers post size charts on their websites that provide ballpark waist and inseam measurements. When you get to know a brand’s sizing practices ahead of time, you’ll save time and won’t be devastated if you need to go up a few sizes when trying on brands that run small.

Katherine Moenning rocks a women’s “skinny” cut. Image via DYKE.

Another popular women’s cut is the “boyfriend.” You can style these Paul Smith “boyfriend jeans” masculine, feminine, and anywhere in between.


If you found the perfect pair of jeans for a couple of bucks at the thrift store, congratulations! Your patience has paid off and you’ve earned your treasure. But, if you find something that is anything less than perfect, put it DOWN. There is no sense in owning a million pair of cheap jeans that do not make you feel amazing. Invest in a few great pairs and take care of them. And, my golden rule: when you find a pair that you absolutely love, buy more than one in multiple washes, especially if you struggle with jeans shopping.


Matt Baldwin, Founder and Designer at Baldwin Denim, believes that, when it comes to jeans shopping, the number one mistake is buying a jean that fits perfectly because it’ll stretch about a full size during your first 30 wears. Always size down.

Menswear blogs from GQ to Esquire have noted that today’s jeans market is so saturated with confusing choices that anyone trying to buy a pair of jeans that just fits is often frustrated.  If your body type doesn’t lend to the latest fit crazes, such as super skinny, do not beat yourself up. Jeans are a wardrobe essential and you should feel confident and comfortable in them. Stick with a classic cut and you won’t go wrong. Here’s some classic fits we love:

Slim Fit
Unlike Saran wrap tight skinny jeans, slim-fit jeans should gently hug the thighs, knees, and calves and loosen up around your ankles.

Slim fit jeans via Esquire

Straight-Leg Fit
Straight-leg jeans should be cut the same all the way down, which will give you a slightly tighter fit around the thighs.
Straight-leg fit via Esquire
Classic Fit
These jeans are loose throughout, so they will not fit tight around your thighs. However, this may cause some “bunching.” Consider getting them hemmed so that you have a 1-inch break or roll them up.
Classic cut via Esquire
Relaxed Fit
With a fuller leg and seat, these are the roomiest of all the jeans. Just be careful not to wear them too “saggy.”
Relaxed fit via Esquire


I get each and every single pair of my jeans tailored. I don’t have a choice. I’ve come to terms with it. I’m a size 4 to 6 and apparently fashion designers believe that if you are anything over a size 2, you must be at least 5’6” tall, which I am not. If you’re not 100% sold on the idea of tailoring, read more here. The key is to start with jeans that fit the largest parts of your body and then have a tailor take in any excess fabric.


You may want to start with at least three pair of perfectly tailored jeans: a dark, medium, and light wash. This way, you will be prepared for all four seasons and have jeans you can wear to a variety of events with different levels of formality (e.g., football at the in-laws, clubbing, casual Fridays). You can add colors, such as white, tan, or gray, once you have the essentials.

Casual classic wash via Esquire

Sporty, predistressed vintage wash via Esquire

Dark rinse jeans can be dressed up or down. Image via Esquire

Raw jeans are untreated, unwashed, and take forever to break in. But, the payoff is a great looking, unique pair of jeans that can be dressed up or down. Image via Esquire


When it comes to the cuff, some say cool, others say tool. I say both cuffed and uncuffed can be dapper if done right. In order to pull off cuffed jeans successfully, you need a pair of jeans that have attractive piping and stitching worth showing off, which is yet another reason to invest in a higher quality jean.
Cuffed via Neiman Marcus
Uncuffed via Esquire
Co-founder of BKLYN Dry Goods, Jahn Hall, who styled and photographed dapperQ’s Queer Country Fashion Show and also held creative and leadership tenures at Diesel and Earnest Sewn, had the following advice to offer our readers:
On Curvy and Plus Sized dapperQs…
The biggest thing to consider is that some men’s denim (particularly those playing off old workwear and denim) often have a square waist, which is a good choice for those with a fuller waist. Men’s jeans still have a ‘waist’ in terms of waist to hip ratio, albeit a slighter proportion than a woman’s jean. If you’re curvier [in the hips/butt] and still prefer men’s denim, a good tailor is a must, as they can help cinch in the waist, if you prefer.

Paris in Vintage Levi’s 505s. Styling and photography by Jahn Hall.

Ariel in Vintage Levi’s 501s. Styling and Photography by Jahn Hall.

On Slim dapperQs…
Brands like J.crew actually have a section dedicated to slim menswear — and Uniqlo stocks men’s denim in smaller sizes.

Look for selvedge…
While it doesn’t mean it’s better in terms of quality than all denim, selvedge denim is made from ring spun threads and uses the natural finished edge of fabric bolts to create the exterior leg seams — like denim was made back in the day. It’s best if you’re looking to rock a cuff.

Denim isn’t made the way it was used to:
Most denim today selling for less than $50 is made from open-end threads, a technique invented to save money and create homogeneity in the 70s by chemically bonding scraps of weaker, shorter fiber cotton to make the thread. Prior to that, all denim was ring-spun, a process whereby only the longest and strongest fibers are spun into threads.

Do your research:
Know what you’re buying. Just because you’re buying a pair of Levi’s doesn’t mean you’re buying the best. Sure, Levi’s offers up a range called LVC (Levi’s Vintage Clothing) based on their archive and made with great consideration of quality — and even their mainline offers up selvedge and U.S. made styles. These styles run anywhere from $175-$350. The Levi’s you find at Wal-Mart for $30 are made from different threads, constructed differently, and aren’t made in the U.S. Different strokes for different folks; however if you’re wanting the real deal, know it’ll never cost $30.
Know your options:
You can get anything in NYC — including a custom-made pair of denim. Loren, based in Greenpoint, will measure you up and make the cut from around $550. It’s not cheap — but we’re talking about a one-of-a-kind pair of denim made for you. If you can’t afford custom-made denim, make nice with your tailor. PS: Loren also offers up denim repair and alterations.Invest in your investment:
Now that you’ve splurged on that $200 pair of denim, it’s best to make ’em last. Wash them…occasionally…at best. True denim heads will go for a year without washing their new raw selvedge denim to get the most desired wear from their investments. When you do wash them, wash them inside out in cold water — and hang them up to dry. The dryer does more to fade out your favorite blues than the washer does!

Levi’s is the classic all-American jean. You can never go wrong with a good pair of Levi’s. They come in a variety of styles and washes, but the ultimate Levi’s fit is the 501, a straight leg jean that sits below the waist with a classic seat and thigh. And, if you’re looking for something a bit more trendy, Levi’s updated their 501 to create the super-close-fitting 511 that has a lower rise and snugger fit without being too skinny. dapperQs from Ariel Speedwagon (pictured above in vintage 501s), Paris (pictured above in vintage 505s), Rachel Maddow, Rocco Katastrophe, and Tiq Milan enjoy a good pair of Levi’s.
Levi’s works for many sizes and genders. Here Tiq Milan (top left), Rocco Katastrophe (bottom left), and Rachel Maddow (right) show the versatility of Levi’s
J Brand
J Brand jeans are a moderately priced premium option, an investment that is more expensive than Levi’s but a fraction of the cost of Dior or Dolce & Gabanna. The L-Word’s Katherine Moenning (Shane) swears by J Brand jeans.
J Brand Kane (style) in Boone (color)
A.P.C. Jeans
A.P.C. jeans are in the same price range as J Brand. According to her Foursquare account, Ellen Degeneres is a fan of their denim.
A.P.C. jeans
Dior Homme
Apparently these are the Rolls-Royce of jeans and a favorite of Lindsay Lohan’s boi toy, Samantha Ronson. GQ instists that what you’re paying for is “a pair of jeans with a crazy good fit and a subtle, intentional wear and tear. A paint and resin splatter here, a crease and whisker there.” If you’ve got an extra $650 weighing you down, I can recommend some great charities that are looking  for donors. But, if you simply must splurge on a pair of mega-pricey jeans, then I suppose these are the ones to buy.
Dior Homme Jeans
H&M Jeans
Still have price tag shock from those Diors? Well, GQ recommends H&M jeans, such as their Drain Denim and Sliq cut, as an affordable option, stating, “Here’s the truth: the treatment and fit of these is nearly indistinguishable from ones 20x’s the price.”
H&M Sliq cut
Lucky Jeans
Founding President and CEO of Riot Grrrl Ink (RGI) (the largest queer record label in the world), Gina Mamone, modeled a pair of Lucky jeans at a dapperQ He Said/We Said photo shoot. Since then, we’ve all been believers.
Gina Mamone in Lucky jeans. Photos by Maro Hagopian.
Women’s Styles We Love
Our readers swear by Abercombie and American Eagle “skinny” jeans, and the Gap usually carries an affordable version of the Paul Smith “boyfriend” jean pictured in the measurements section.  Sonny Oram, Founder of Qwear, is a fan of Abercombie’s “Erin Skinny” jean, while my fiancé, Senka, has a slightly obsessive collection of American Eagle skinny jeans in a variety of washes.  And, dapperQ contributor Ariel seconds Senka’s positive appraisals of American Eagle jeans, particularly their Slim Straight fit.

Sonny Oram in Abercombie’s “Erin Skinny” jean. Photo Courtesy Sonny Oram of Qwear.

Ariel in American Eagle Slim Straight Jeans

Senka in American Eagle SkinnyJeans

Gap “boyfriend” cut jeans

Tags from the story
, , ,
More from Anita Dolce Vita

Interview: O’Hooley & Tidow’s New Album

The dapper Belinda O’Hooley and Heidi Tidow of the British chamber-folk duo...
Read More


  • I am looking for another brand to the Levi’s 550 that I have been wearing. Any suggestions other than going to the stores and trying all the brands.

    Your suggests would be welcome.

    thanks, stephen

  • Hi, I’m trying to help a male friend buy a pair of jeans. He’s built like an athlete — tall and slim, with muscular thighs. He’s having trouble finding jeans that fit around his waist and thighs. What brands would you recommend? Thanks!

  • Nice article,shopping for jeans has always been a frustration for me. Now i have some insights on what to look for next time i go shopping.

  • Hi Anita, i liked your article and all the aspects are clearly explained. Well one of my friend always trouble finding a right type of denim for him. He has slim body and medium height but he never find a prefect waist fit jeans for him. So can you please suggest some brands which he can look for?

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.