Preppy Washington 2018

Inside the Tuckernuck store

1. Tuckernuck

Born as an alternative to J-Crew, Tuckernuck started online before opening a store in the university district of Georgetown. The brand – named after an island off Nantucket – specialises in what co-founder Jocelyn Gailliot describes as classic all-American wear: structured dresses, wool blazers and plenty of stripes. The shop also sells homewares and will monogram any clothing you buy there and then.

Tuckernuck, 1052 Potomac St, NW Washington, DC 20007

Gift items from Trunk Club store

2. International Spy Museum

Located on the top floor of the International Spy Museum in Penn Quarter, Trunk Club is a good option for those who like the best brands, but don’t enjoy traipsing round the shops to find them. Make an appointment to meet a stylist online, who, having asked a few questions about your style preferences will pick you out a series of outfits. Where usually the stylists would post their selections to you in a box, visiting the Clubhouse gives you the added bonus of being able to try everything on.

Trunk CLub, 525 9th Street NW Suite 700, Washington, DC 20004

Inside the Read Wall store

3. Read Wall

3. ‘Part men’s club, part library, part classy frat house,’ Read Wall’s stores should be a first port of call for anyone looking for classic American tailoring. Inspired by the dress sense of JFK, Ernest Hemingway and Steve McQueen, it offers everything from made-to measure business casual pieces to tailored sportswear and wedding attire. Scheduled appointments are recommended in order to get the full custom experience (and to allow them to stock the bar). And, the brand will give a book to a child in need for every product sold.

Read Wall, 1921 8th Street, NW Washington, DC 20001

Hugh & Crye shirt

4. Hugh & Crye

With 12 sizes to choose from, Hugh & Crye believes it has a shirt to fit every man, from the short and skinny to the tall and broad. Rather than asking for the usual measurements – neck and chest size – shop assistants take note of your muscle mass in order to get the perfect size. Shirts range from $85-105 and always fit brilliantly.

Hugh & Crye, 3212 O St. NW #5, Washington, DC 20007

Inside the Ledbury store

5. Ledbury

Ledbury was formed by two local boys from Virginia who, having finished their degrees at Oxford University, became apprentices at a shirt maker on London’s Jermyn Street. The store began by selling dress shirts, but has branched out into blazers, sweaters, trousers and accessories, all crafted with fabrics from European mills. After years of successful pop-ups, Ledbury has established a permanent home in Georgetown’s Cady’s Alley, offering both ready-to-wear collections and made-to-measure appointments.

Ledbury, 3319A Cady’s Alley NW, Washington, DC 20007

Inside Paul Stuart tailor's store

6. Paul Stuart

Paul Stuart, New York’s Madison Avenue tailor, opened a store in CityCenterDC two years ago. The brand isn’t a million miles from Ralph Lauren and Brooks Brothers, but what sets it apart is the new luxury line, Made on Madison – an array of hand-sewn robes, scarves and shawls for men and women, along with some excellent pyjamas.

Paul Stuart, 906 I Street, NW Washington, DC 20001

The Lucky Knot storefront

7. The Lucky Knot

There’s no better place to get decked out for a weekend’s sailing than nautical retailer, The Lucky Knot. Andrea Ploutis and her three daughters own the boutique – located in Old Town Alexandria – and traverse the States in search of classic American men’s and womenswear suitable for the beach and the boat. Look out for a great selection of croakies (sunglasses straps) and koozies (can coolers) – they’re not that easy to come by.

The Lucky Knot, 101 King Street, Alexandria, VA 22314

Inside the Vineyard Vines store

8. Vineyard Vines

Vineyard Vines began life in 1998, distributing ties in order to finance a life aquatic for founders Shep and Ian. Today, the brand has six stores nationwide (its latest on Wisconsin Avenue) selling clothes for the whole family, inspired by the nautical style of Martha’s Vineyard, the popular tourist destination just south of Cape Cod. This year, the brand is the official style sponsor of the America’s Cup and has added a new range of performance wear to its catalogue.

Vineyard Vines, 1225 Wisconsin Avenue NW, Washington, DC 20007