Dress Shirts
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Men's Dress Shirts Built for Canadian Life Since 1909
Dress Shirts
Tip Top has sold men's dress shirts in Canada since 1909, and the collection still starts with the same question a good associate asks in store: what's the occasion? A wedding needs a crisp white collar. A job interview needs a shirt that looks pressed at 4 p.m. A long week at the office needs non-iron cotton that survives the dryer.
Our dress shirts for men come in Modern Fit and Slim Fit, in wrinkle-free sateen, stretch weaves and easy-care cotton, and you can buy them online or try them on at any of our 102 stores.
Sharp style, made simple. Your shirt for every event.
Why Choose Tip Top for Men's Dress Shirts?
Proudly Canadian Since 1909
Tip Top started as a Toronto tailor more than 115 years ago. That history shows up in the details that matter on a dress shirt: a collar that sits flat under a tie, sleeves cut in real lengths, and prices built for everyday Canadian wardrobes instead of a luxury markup.
Designed for Life's Events
Most men buy a dress shirt for a reason. Ours are built around those reasons. Choose a white sateen shirt for the ceremony, a light blue shirt for the interview, or a patterned Hechter Paris shirt for the reception afterparty. Wear it buttoned under a suit, or open-collar with chinos when the dress code says business casual.
Modern Fit and Slim Fit for Every Body Type
Modern Fit is cut straight, with extra room through the chest, shoulders and arms. Slim Fit tapers from chest to waist for a closer line. Neither one needs alterations to look right, and many styles add stretch, like our 360 stretch dress shirts, so you can reach and dance without pulling at the buttons.
Easy-Care Fabrics That Travel Well
Bellissimo non-iron sateen comes out of the wash smooth. Grafton 1853 non-iron prints hold their shape through a carry-on and a hotel closet. Stain-release finishes help a white shirt stay white after the coffee spill. Hang it overnight and it's ready.
Convenient Shopping and Hassle-Free Returns
Order online with free shipping over $99, or pick a size in person with an associate who fits dress shirts every day. Returns and exchanges run through our online Returns Centre. Select stores also offer in-house tailoring for sleeve-length adjustments, often the same day.
Find Your Perfect Dress Shirt Fit
Fit decides whether a shirt looks bought or looks borrowed. Start with the cut, then confirm your numbers.
Modern Fit, Slim Fit, and Classic Fit Explained
- Modern Fit: a straight cut with room through the chest, shoulders and arms. It suits broader builds, all-day office wear and anyone layering a vest or sweater on top.
- Slim Fit: tapered from chest to waist with narrower sleeves. It reads sharp and contemporary, and it tucks cleanly without extra fabric bunching at the belt.
- Classic Fit: the fullest, most traditional cut, sometimes sold as regular fit. If that's the shirt you've worn for years, Modern Fit is the closest match in the Tip Top range and gives you the same comfort with a cleaner line.
Not sure? Try one of each in store. Two minutes in a fitting room settles it.
Sizing Guide: Collar, Chest, and Sleeve Length
A dress shirt fits when three numbers line up. Measure these before you order:
- Neck size: wrap a soft tape around the base of your neck and leave room for one finger underneath.
- Chest: measure around the fullest part, under the arms, with the tape level.
- Sleeve length: start at the centre back of your neck, run across the shoulder and down to the wrist, arm slightly bent.
Match those numbers to our dress shirt size guide, then pick your fit. Between sizes? Go with the collar that closes comfortably and let a tailor handle the sleeve.
Dress Shirts by Colour
Colour sets the tone before anyone notices the fabric. These are the shades Canadian men ask for most, from boardroom basics to shirts built for a party.
White Dress Shirts
Buy a white dress shirt first. It works under a navy suit at a wedding, a charcoal suit at an interview and a tux jacket at black tie (a pleated tuxedo shirt is the formal option there). Choose sateen for a formal sheen, or 100% cotton from Grafton 1853 or Hechter Paris for everyday wear.
Black Dress Shirts
A black dress shirt goes from desk to dinner. Swap the jacket, done. Wear it under a black or grey suit for a tonal look, or on its own with dark trousers. For evening, sateen gives it a subtle sheen.
Red Dress Shirts
Red is the confident pick for holiday parties, festive dinners and semi-formal events where you want to be remembered. Keep the rest of the outfit quiet, a navy suit and a dark tie, and let the shirt do the talking.
Purple Dress Shirts
Purple adds colour without shouting. A lavender or plum dress shirt looks sharp at a spring wedding and works on a regular office day under a grey suit. It also pairs well with silver or navy ties.
Blue Dress Shirts
A light blue dress shirt is what most men reach for on a Monday, and for good reason: it flatters most skin tones and matches nearly every suit colour. Deeper blues and navy suit evenings and business casual.
Grey Dress Shirts
Grey is the understated option. A light grey dress shirt softens a black suit, while a darker grey works on its own with navy trousers. It's the easy choice when white feels too formal.
Boys' Dress Shirts
Ring bearers and junior groomsmen need shirts too. Tip Top boys' dress shirts use the same easy-care Bellissimo sateen as the men's line, so a father and son can match at a wedding, a graduation or a school concert without anyone ironing at 7 a.m.
Short-Sleeve Sport Shirts
Summer weddings and hot office days call for something lighter. Our short-sleeve sport shirts come in cotton and soft-touch blends from Hechter Paris and Jermyn & Bond, so they look finished with dress pants and relaxed with chinos. A short sleeve dress shirt is fine for a patio ceremony; keep a long sleeve dress shirt for anything with a tie.
Smart Pairings: Style Your Dress Shirt with Tip Top Wardrobe Staples
A dress shirt is one piece of the outfit. Build the rest in one visit.
Suits
Start with a Tip Top suit in navy, grey or black. Match a white or light blue shirt for interviews and weddings; save bolder colours for events with a looser dress code.
Dress Pants
Dress pants in charcoal, navy or khaki turn a dress shirt into business casual without a jacket. Look for wrinkle-resistant fabric if you commute.
Ties and Bow Ties
A solid silk tie keeps things formal. A pattern adds personality at a wedding or prom. Our ties and bow ties come in colours chosen to sit well with our shirts.
Vests
Layer a men's vest over your dress shirt for a three-piece wedding look, or wear it without a jacket at a relaxed reception.
Blazers and Sport Jackets
A sport jacket or blazer over an open-collar shirt is the easiest smart-casual outfit there is. It works for dinners, date nights and client lunches.
Accessories
Cufflinks, a leather belt and a pocket square finish the outfit. Belts, suspenders and tie bars are all in the accessories range too.
One shirt, a good tie and the right fit will carry you through most of the year's big days.
Frequently Asked Questions
What's the difference between Modern Fit and Slim Fit dress shirts?
Modern Fit is cut straight with extra room through the chest, shoulders and arms. Slim Fit narrows from chest to waist for a closer, more tailored silhouette. Pick Modern Fit for comfort and layering, and Slim Fit if you prefer a trim line under a jacket.
Are Tip Top dress shirts wrinkle-resistant?
Yes. Many Tip Top dress shirts are non-iron or wrinkle-resistant, including the Bellissimo sateen and Grafton 1853 lines. Every shirt in the collection is machine washable. A quick press only helps with the collar and cuffs on a big day.
How do I measure for the right dress shirt size?
Measure your neck size with one finger of room, your chest at its fullest point and your sleeve length from the centre back of your neck to your wrist. Compare the numbers with our size guide, then choose Modern Fit or Slim Fit. An associate at any store can measure you in a few minutes.
Does Tip Top offer in-store tailoring for dress shirts?
Select Tip Top stores offer in-house tailoring for sleeve-length adjustments, often same-day. Call or visit your nearest store to confirm what your location offers before you shop.
Find Your Perfect Dress Shirt at Tip Top
The right dress shirt should fit on the first try and look good for years. Tip Top carries men's dress shirts from Bellissimo, Grafton 1853 and Hechter Paris in Modern Fit and Slim Fit, with non-iron, stretch and stain-release fabrics built for Canadian workdays and weekend events. Shop the collection online, or find men's dress shirts in our stores across Canada and let an associate find your size.
Searching for "dress shirts for men near me"?
Tip Top has 102 stores across Canada, including Eglinton Square in Toronto, Square One in Mississauga, Market Mall in Calgary, Polo Park in Winnipeg and Halifax Shopping Centre. Walk in, try a few collars and leave with a shirt that fits.
H6: Visit a Tip Top store or shop our men's dress shirt collection online. Your next shirt is one fitting away.
Find the store closest to you in our Store Locator.
